The Bill Simmons Podcast - KD's Out, Kyrie's Leaving, and Jeselnik Is Still Funny—With Bill's Dad, Sean Grande, and Anthony Jeselnik | The Bill Simmons Podcast

Episode Date: May 9, 2019

HBO and The Ringer's Bill Simmons is joined by his dad to talk about the Rockets letting another playoff game slip through their fingers and the end of the Celtics' season (2:50). Then they are joined by longtime Celtics radio play-by-play announcer Sean Grande to reexamine Boston's season, where it went wrong, and why it couldn't be fixed (25:30). Finally Bill sits down with comedian Anthony Jeselnik to discuss edgy tweets, comedy roasts, gambling, sports, Jesilnik's new Netflix comedy special 'Fire in the Maternity Ward,' and more (1:00:50). Learn more about your ad choices. Visit podcastchoices.com/adchoices

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Go to DAZN.com to sign up. That is D-A-Z-N. We're also brought to you by the Ringer Podcast Network, where you can find all kinds of awesome podcasts, including Binge Mode, our Game of Thrones podcast, the most popular Game of Thrones podcast. Only a couple of them left. And the new one went up, breaking down season four. Sad to say only a couple left.

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youtube channel because we've been doing a lot of fun stuff on there as well, including the trailer for It Too came out. And we like to do a little office trailer premieres. And we just taped that one in Chris Ryan's office, actually. The Ringer staff and myself and the Simmons family, most importantly, because my son has seen the original It from two years ago about 25 times. Very excited for It 2.

So check that out on YouTube, youtube.com slash ringer. And you can also find Throne Game with me and Rosillo. We have cut all of those parts out of the podcast, and we have made them YouTube clips. So you can catch up on those. You can watch them for the rest of your life. YouTube is eternal. It'll live on forever. Coming up, Anthony Jeselnik is coming up a little bit later.

Second podcast with him. One of our favorites. He has a new Netflix special coming out, or it's actually out, I'm sorry, that we talk about, but we also talk about the comedy scene and a whole bunch of stuff, some sports. He's coming up later. My dad is here now. Obviously, we have to have a eulogy for the Celtics season. We're going to call Sean Grandy as well to get his perspective of somebody who's been forced to ride the team plane with these guys. But first, our friends from Pearl Jam. All right, my dad is here. We thought we'd be watching game six of the Bucs series on Friday night,

but that's been canceled because the Bucs finished the series off. We can talk about the Celtics in a second. We watched the Warriors-Rockets game this morning, and Durant goes out, and it's all on a platter for the Rockets. This is the break they finally needed. This is it. This is their chance.

Close game. They come back. It's sitting there for them, and they don't get it done. Felt like another lost opportunity for them. It was the strangest fourth quarter though. We were talking, where's Harden? Where's Harden?

Where's Harden? Yeah. And he might've only scored three points. I don't have the exact number, but he never had the ball. He scored, he came back with like a little over seven minutes left and only scored at the tail end of the game. And it was effectively garbage time, although it did cut it to three and they almost got a ball and a steal.

But they had to foul at the end. And I watched this Twitter thread where Brett, where somebody who covers the Rockets broke down every possession in the last seven minutes. And it was interesting. They actually made the right decisions. Almost every time there was one play, like a little under four left when

Chris Paul just decided to take Kavon Looney off the dribble and he ended up getting a charge. For the most part, he was pretty unselfish. I guess my question is, the whole year you haven't been unselfish. It's been this offense where you have the ball 40 feet

from the hoop, everybody spreads out, and you do your thing. It was hard to understand why they weren't doing that last night. It was like he deferred to Chris Paul. It really did seem that way. Who hasn't played that well this series? And who would you rather have in a very winnable game with the

ran out? I don't want 45-year-old Chris Paul dribbling around. I want Harden with the ball, if I'm a Houston fan. Yeah, it was weird. It seems like they overthought the matchups a little bit because once Durant goes out, you know,

less rim protection for the Warriors. Although I guess Looney, I still like Durant more as a rim protector, but it just seemed like they felt like, oh, cool. Now we can exploit Looney with Chris Paul. And it's like, you have a guy on your

team who had one of the best offensive seasons of the last 40 years. I'm pretty sure the Chris Paul-Looney matchup isn't like your mojo here. You know, I don't want to... It just reminded me of when Harden had that awful game seven.

But he wasn't bad in this game. He was like 10 for 16. No, but it's like he almost didn't go and get the ball. He didn't want the ball. Oh, now we sound like we're on first take. James Harden, come get the ball! I want Harden with the ball. I'm not a Rocket fan,

although I would rather see the Rockets win the series. What, because you met Darryl once? More than once. You're like a Sloan Conference VIP. He got me a ticket into Sloan Conference. So now you're rooting for the Rockets. What have the Warriors done for you? Nothing.

So I want Harden with the ball. Again, Chris Paul is my age. I don't want him dribbling around in the fourth quarter. It's, what do you, as somebody who's seen every point guard ever dating back to Bob Cousy and Bob Davies in the 1950s, where does Chris Paul rank for you? All-time point guards. He's in the top 50. A notch below Isaiah?

Yes. Detroit Isaiah, not this decade Isaiah. Detroit Isaiah, sure. decade Isaiah. Detroit Isaiah, sure. Oh, certainly below Isaiah. What's your point guard list? Oh, I... I'm going to give you Magic, Isaiah, Oscar Robertson, Walt Frazier, who you were really bullish on,

Chris Paul, Nash, Bob Cousy. I'd have to have them all written out, but my favorite point... I just listed all of them. My favorite point guard of all time was Walt Frazier. Make the Walt Frazier case. Well, the 70 and 72 championship teams, he had charisma,

he had style, he had game. He played in the most famous city at the time for basketball. Yeah. He had style. He had game. He played in the most famous city at the time for basketball. Yeah. He had it all. And he came up big in big moments. I was just going to say that. As opposed to what happened yesterday with Harden last night.

Yeah. Frazier wanted the ball, and he made the big basket when he needed it. And he was surrounded by great teammates who wanted him to have the ball. And that didn't seem to happen last night. I mean, it was a strange fourth quarter. I remember when I was researching my book and I got a hold of, it's funny now because a lot of this stuff's on YouTube,

but I got a hold of game seven of 1973, the series, the Celtics were the best team that year. Havracek separates his shoulder. But it ends up going game seven in Boston anyway. And they had the video of the game, but there was no audio. It was just the video. And he's watching the second half and Frazier just over and over again, he's dribbling to the same spot, top of the key, like 19 feet away with his back to the guy, backing him down to the spot he wanted and then a little turnaround.

Right. And I was like, it was kind of eerie watching it. It was like, oh my God, they can't. But then you're also watching it from the prism of the way we play basketball now where you're going like, why don't they send a second guy at him? Like, why are they just letting him do this over and over?

He was an assassin though. Well, it's ironic because it was that series, as you probably remember, after New York won and we lost that series, that prompted me

to go down to the Celtic season ticket office and get season tickets. Yeah. Because we had just lost, there were some tickets available and that led to, what, 46 years of watching the Celtics.

And unfortunately, it's probably a good segue into this was one of the worst years I can ever remember watching as a fan, this Celtic team. It was, yeah, it's the worst case scenario for a season where you have a ton of talent and the talent doesn't mesh and it's an unlikable team. And then. We didn't know it would be an unlikable team. Last September. Oh, my God. I mean, shit.

Our expectations. I'm on record. There's videos of me saying how they're going to roll through the Eastern Conference. I thought they would win 67 games. LeBron's gone. It was all lined up. Yeah. Giannis through the Eastern Conference. I thought they were going to win 67 games. LeBron's gone. It was all lined up. Giannis was the X factor. I mean, actually, Giannis and Kawhi were the two X factors.

It's like, and I remember for the year, we picked, not you and me, when me, Sal and Haas were doing our things, we thought Giannis was the best odds. It was like five to one. It was like this. There are signs that point to him having like a breakout MVP year and then the other one was like

ah Kawhi if he's healthy he was a wild card but it was like the good version of the Kawhi season is like

if he's healthy and in the playoffs that's going to be a dangerous team but who knows so now you have Giannis come through you have Kawhi

come through and then on the flip side Boston Craters and Philly seems like they're crumbling we'll know we'll know tonight we'll know more tonight I'm not optimistic but you know Kawhi come through. And then on the flip side, Boston, Craters, and Philly. Seems like they're crumbling. We'll know tonight. We'll know more tonight. I'm not optimistic.

But you know, Milwaukee also did a, I mean, they obviously looked at what happened last year when they lost the seven-game series against the Celts. Yeah. I thought they did a terrific job bringing in three players to surround Giannis. Well, one of them was your all-time favorite random league pass guy, Brooke Lopez, who is now just a three-point shooter. You're right.

They brought in four guys. I wanted Brooke Lopez on the Salts. I mean, he was available for cheap money. You and I are both tainted by Brooke Lopez because there was that one year where we had Brooklyn's pick and we were watching the games rooting against him and Brook Lopez was just single-handedly killing our pick. He was.

And scoring game-winning buzzer shots and 45 points and all this. We were like, this guy's the best player in the league. So they brought in Brook Lopez, who's a eight-foot-tall, three-point shooting center. Yeah. They bring in Meretic. They bring in Hill, who I thought had a career year off the bench from Milwaukee.

And looked like he was walking dead last year. Add him to the list of people who you've put them with LeBron and they just become worse. And Ila Solver, if I say his name correctly. You went three out of four with the names. Okay, not bad. Meritage was the only one who got wrong. So they brought in four guys, all of whom shoot the three. Well, you left out Connaughton, who killed us in that Boston series.

Well, he was already on the team. He just got better. I thought they signed him from Portland. Wasn't he in Portland last year? Oh, maybe you're right. They got him within the last year and a half. Arlington's own, Pat Connaughton. They looked at the tape. They saw that teams

were triple teaming Giannis when he went, when he was well, remember last year in the playoffs, we're just leaving Tony Snell up and leaving a, who's the other guy? Well, Middleton Jabari Parker. Middleton had a good series but it was like Tony Snell, Jabari Parker Thon maker. Yeah. We were just letting all those

guys. Good luck. Good luck. Good luck. So they were a much better team this year. Where does Giannis rank for, you've had season tickets since 74 of most incredible people you've seen in person. Is he like in the top six now? He probably is. He's got to be, right?

He certainly is for me. I can't think of another athlete who he reminds me of. No, it's basically like Dr. J in the late 70s if Dr. J was like seven inches taller. Seven inches taller. And now you're not afraid. If I'm a Milwaukee fan, I don't mind when Giannis takes the three-point shot. I mean, he's not terrible.

Well, it's the difference in him and Simmons on Philly where he wasn't good at it, but he kept taking them and they kept telling them to take them. And it's like, you just have to do it. Like, even if you miss them, maybe we'll get the rebound, but you can't not take a couple a game. And now he seems relatively, I mean, he's not like an assassin, but he's relatively comfortable.

And I know we'll talk about Kyrie, but I'd love to have him on my team. He's an ambassador for the sport. His teammates seem to love Giannis. He's coachable. Yeah. He's a great teammate. We could have had him, by the way. I know that.

We took Kelly and Lennox over him. I remember. He was only 6'9", though. He grew three inches after. We traded down for the 13th pick, or traded up, I guess you call it. I remember. He was only 6'9", though. He grew three inches after. We traded down for the 13th pick, or traded up, I guess you call it. Took Kelly. We wanted the number, we wanted the guy who won ahead of Kelly.

You usually love when your teams trade up. Yeah, I do. If you were a GM, you would just be trading up every, the Patriots would have just traded up at every draft. We have no players. You would have traded up this year. We would have great players because we traded up what do you mean?

the one year we traded up for Chandler Jones you were the most excited you've been in like 10 years well I was still excited until he was naked in the police station I forgot about that he was shirtless he wasn't naked who was the guy you wanted to trade up for this year?

Hollywood, the wide receiver. No. Was that the guy? Or the tight end, Noah Fant? No, the tight end. You wanted one of them. Noah Fant. Yeah. When the Celtics traded down from the false pick a couple years ago, you were really upset. You didn't like that. I made a mistake

on that one. I would say Philly made a bigger mistake. Yeah. It's funny with this Philly made a bigger mistake. Yeah. It's funny with this Philly thing where they had basically the number one pick two years in a row.

But then nobody's talking about it. And Embiid, who was the third pick in the draft. They had Okafor, who was fourth. Right.

And they basically have one and a half guys now. They have Simmons, who's been a really good regular season player and cannot be played in the playoffs until they figure out how to use him, and they just can't.

Now, I don't know if another coach could figure out how to use him, but it's really kind of weird watching their half-court offense and just like clogging the paint. Simmons is taking a lot of heat for what's happening. He should be. I don't understand how you don't know how to really shoot at all

when you're a professional basketball player. Not just that, but your job is to be a professional basketball player. Yeah. This is it. You're not making movies. You're not doing... Well, unless you're Kyrie.

Yeah. Sure. But don't you spend the whole summer shooting jump shots? I mean... I would just assume he would at least have a 17-footer by now. I feel like if my son, who's 11, if I had him out there three hours a day shooting a 17-footer,

he would become decent at it by the end of the summer. He's 11. It's hard to figure, but... Very strange. Which team would you rather be right now, Boston or Philly? Next five years. Boy well that's a tough one because I think we have more

unknowns than Philly does I mean we have tremendous unknowns for this summer well especially we have four first rounders but none of them are top shelf

we have four first rounders in your draft where everybody only likes like five players right and we have like the ninth pick and down right and we have the Kyrie situation where and then the Horford situation the Horford can opt out he can opt out I think he might we have Rozier who's restricted somebody's gonna throw him a lot of money well I'm driving Kyrie to the. I think you said you would take Rozier. Well, if Kyrie's flying away, I don't know who our point guard is. That's the only... But could you do another year of Rozier?

Just mentally and physically, could you do it again? I don't think I could. I think... I'm trying to think your type... It's funny, the Celtics team hit the triple crown for me. Cause my least favorite things with basketball are 25 footers, lazy defense and finger pointing your least favorite thing. You hate all of those things,

but your least favorite thing is the 20 footer with 18 seconds left on the shot clock is the all time bane of your existence. And that's really a Rozier specialty. That's one of his moves. He's on the shot clock. Right. Is the all-time bane of your existence. And that's really a Rozier specialty. That's one of his moves. He's not the only one. It worked in the playoffs last year somehow for a couple rounds. I think when they're practicing outside shooting, I think Tatum, Smart, and Rozier keep taking the same shot.

And it's that 22-footer with 18 seconds left on the clock. That all the advanced metrics say don't take the shot ever. And the lane is wide open and they can go in and maybe get fouled or at least maybe even make the shot. I don't know if... Sometimes I worry that Tatum just is the guy... What we're watching, is he just going to be this guy? You know, when you look at this season, all the disappointments,

Tatum, well, I guess Kyrie has to be number one. I mean, I don't know how you, but certainly number two would be Tatum. I agree. At least Hayward had an excuse. He seemed like he had PTSD from that injury. The Hayward stuff, I blame

and I wouldn't have been blaming Stevens a year ago for anything, and I wouldn't have been blaming Stevens a year ago for anything, but I think they made a huge mistake depending on him too quickly. Yeah. They should have brought him in really slowly. We noticed that

when we went to the Orlando game together. Back in November. And he just didn't seem right. We left the game and they were super disjointed, but we left the game. We're like, why are they rushing Hayward back?

He doesn't seem right. They rushed him. They started him right away. I think that created some bad feelings from the players who had been there a year ago. Right, he hadn't earned his spot. No, and they should have brought him off the bench 10 minutes a game.

You know, it's sad though because I went to the games February, March, April. Hayward was slowly after All-Star break he looked like he got his mojo back and I don't know

what happened in this Milwaukee series he looked like a guy who was scared to death to go near the basket yeah and he

and Kyrie's gonna take all the heat and he should but I gotta say I was shocked by how bad Hayward was because he seemed scared.

He was, this game that, in April, this slashing kick game that he had was really starting to come back and he was really athletic and fearless and he was challenging people going to the rim.

And he was even doing it a little bit in the Indiana series. A little bit, yeah. And then something happened in the Milwaukee series and instead of being a slashing kick guy, he was just a kick guy. Yeah. bit in the Indiana series. A little bit, yeah. And then something happened in the Milwaukee series, and instead of being a slashing kick guy, he was just a kick guy. And even when he was trying to go to the rim, it was like Giannis had him psyched out or something. I don't know what was going on with him, but he was like a shell of himself again. Well, you and I, when we're at the game,

because the seats are so close to the bench, I watch Body Language a lot. Yeah, you're the original Body Language doctor. I like to call myself the body language doctor, but you were the original. You're the Jonas Salk of body language. There was a consistent theme with Haywood. Every time he missed a shot or a shot went awry in terms of a pass, he'd be shaking his head. Hang dog. Hang dog. Yeah. And he's not the only one. I mean, Irving should get the Oscar for that. Yeah. I mean, if his shot doesn't go in, he doesn't play defense. You think that's a problem?

Well, I think it kind of hurts when four guys are playing. Actually, I don't even know if we had four guys playing defense. Well, the last couple games, and this yesterday, look, you can go back and listen to the podcast I did on Tuesday night with Ursula at house. I was like, the Celtics are done. They're making vacation puts already. And the defense, the last couple games, that 60-second sequence last night when Milwaukee gets like six offensive rebounds

and Kyrie looks like, I don't know what he's doing, but it's almost iconic. It's like the defining minute of this season. He looks like a little kid in a playground who should be on a leash, those little kids on a leash who don't really know where to go and they're just kind of staggering around.

He's just kind of staggering around. The ball's bouncing over his head. His guy's running behind him. I don't know. It's unbelievable. Yeah, they kept showing that on ESPN today. It's unbelievable. Like, you could just put a giant spotlight over him and be like,

what is this guy doing? I think he's waiting for the fast break that never happens because Milwaukee gets six shots. Then there was another great play yesterday when he had the, he drove into the defense. Four guys collapsed on him. Four guys. Four him. Four guys. Four of the five guys on the court from Milwaukee,

they collapsed on him because they know he's going to ball hog it. And they end up tying him up. He comes out of this huddle of four bucks and just starts yelling at Tatum. It's like, what did Tatum do? He just dribbled into four guys. I can't imagine how much they must have hated

playing with him by the end of the season. I think Horford specifically, because Horford, incredible playoff player. Somebody who definitely got better than when it mattered last season. And in general, he's just been in a lot of big games and just as reliable.

Even he seemed like he wanted out of there by the last two games. And his wife had to tweet about it today too. As you know, I went to the game Friday night, game three. Oh yeah, you went to three and four. Monday night, game four. And I mean, we were in the game, maybe even had the lead in both games at halftime.

We're certainly close. Third quarter, our defense just wasn't there. And you could see in the huddle. You like to study the huddle. Well, it's one of my real concerns about what happened at the end of this year. It looked like Stevens lost the huddle. Yeah.

It looked like... Guys were looking at the video screen? Yes. And really not paying attention. And we've seen that before with teams where they check out. Well, remember the Patino team? Yeah, but Patino- Those guys were like playing cards in the huddle,

not even listening to them. They were just like- But would you have ever expected that from a Stevens team? I think the team was just ready to go home. I think they, once Kyrie said the July 1st thing, three, four months ago, and just completely backtracked on, I think that was it. It became the Batan Death March. Well, as you know, I was at the season ticket.

They had a special- Yeah, you went to that. Special night for season ticket holders and Kyrie gets out there and, you know, of course, at that time, we were so excited that he was going to come back. And now, as you said, you want to drive him to the airplane. Airport, yeah. Things have changed. My concern, though, is, you know, he leaves.

It's not like other leagues where somebody leaves and you get a compensatory draft pick or, you know, we're left with nothing. Yeah. And now the Anthony Davis trade, I don't know how you can put all your chips into maybe one year of Anthony Davis. I don't know what they do. Let's put those two together. Two reliable teammates. Well, that's a valid point.

We're going to call Sean Grandy in one second. Sean Grandy is the radio voice of the Celtics. I think he's the most underrated play-by-play guy out there, but more importantly, has traveled with a lot of Celtics teams over this century. And I just want to get a sense from him of what he saw this season. But first, we're going to take a quick break.

Let's talk about Luminary. If you didn't know, The Ringer's new show, The Rewatchables 1999 is available only on Luminary. It dissects the most iconic and 1999-ish movies from one of the all-time great movie years. So far we did American Pie,

we did Cruel Intentions, and this week, Big Daddy, me and Joe House. So you can check that out. Same categories that we have in the rewatchables, plus we added a couple to make it a little more 1999-ish.

Notting Hill coming next week, by the way. I am not on that one. Luminary also has great podcasts from Hannibal Buress, Trevor Noah, and many others. They give you access to a bunch of other shows, all original from innovative, dynamic creators.

Plus, their app is free to download. Use it to listen to thousands of podcasts, including this one. Get first two months of access to Luminary's premium content for free when you sign up at luminary.link slash Simmons. After that, it is $7.99 per month. Luminary.link slash Simmons. For two, it is $7.99 per month. Luminary.link slash Simmons for two months of free access. Cancel anytime. Terms apply.

All right. He's in Massachusetts and he is doing a podcast radio hit tour today. Sean Grandy. We booked him. We were able to book him for 10 minutes here, 20 minutes, whatever this is. First of all, how are you? I am, well, I'm always fascinated as to when you choose to make this call, because thinking about it, I don't get to watch Game of Thrones in real time, right? So I'm sort of disqualified there. I've never directed Denzel or Ray Allen in the scene or have a great story like that. And the only thing I know about the Celtics season is that I've never directed Denzel or Ray Allen in the scene or have a great story like that. And the only thing I know about the Celtics season is that I'll never, ever get on the

rewatchables talking about it because no one will ever want to see another minute of it again. Oh, that's good. I like how there was like a ringer plug there. That was smart. Is this, you've been, how many Celtics seasons is this for you? Like 17, 18? Yeah, this is the last 18.

That's just a long, I'm starting to get that long time voice of the Celtics. Now people for you? Like 17, 18? Yeah, this is the last 18. That's just a long, I'm starting to get that long time voice of the Celtics. Now people sneak that in. Oh no. Like, like, like Jim Ross, long time voice. I told Danny H asked me about that the other day. I heard them call you the long time voice of the Celtics. And I said, you realize, and you know,

a great literary reference in back to school, Thornton Mellon says, if you want to look thin, you surround yourself with fat people. I realized being around Mike and Tommy all these years gives you a sort of a false sense of security about your youth. Yeah, that's true. You think, oh yeah, because I'm still the young guy with Max and Tommy, you know, Mike Gorman and Tommy Heitzen for the uninitiated. And you realize, you know, at our age, we're pretty close in age, you realize it's just a matter of who you're hanging around with.

I think long time is better than veteran. Veteran feels insulting. Like veteran announcer Sean Grandy sounds insulting. Long time sounds like you've been hanging around. Well, I'm a long time season ticket holder. Right. You're not a veteran season ticket holder. Yeah.

But I have 46 years. I have a lot of years. I did not call you during the season because I've been trying not to go on tilt for this whole time. It barely happened once when I flipped out and said I would drive Kyrie to the airport. But this team had so much talent and the way the internet works now when stuff gets thrown back in your face left and right, I just was really trying to rein myself in and I would save all of my barbs and sarcastic comments and anger for just people that work for the ringer and my family. So now I can let it out. I hated this season. I hated the way they played.

I don't understand what happened. I didn't understand what was happening as it was happening. I didn't understand why nobody could fix it. I knew how this season was going to end the moment they fell apart in game three. Why couldn't anyone stop this? What was your expert opinion on this, having been there day in and day out for the last eight months? It really was the movie you had waited to see for so long, right? I got to see this movie. I got, I can't wait until this, the first day of this movie and you go and see it. And it's just from the start, this isn't right. It'll get, well, it'll get better. It'll get,

and it never gets better. And it ended up like last night was like people's reaction to the last episode of lost walking out. I just wasted all that time. What happened? It clearly from the beginning, just never fit together. And there has to be a desire at some point, not just to say you're going to fix it, but to actually do it. And these pieces, you can sit there with the definition of insanity, right? Repeating the same behavior over and over again. These were square pegs and round holes. And it was seven months of getting headaches just trying to jam the pieces in place that never, ever fit.

Why do you think they didn't make a move in February when it was clear that it was clear to all of us, the pieces didn't fit. And I thought for sure, like at the, you know, I have no idea why they didn't trade Roger because it was clear even heading into the season, he wasn't going to have enough. Maybe it was the fourth guard after playing as a starter in the Eastern conference finals. And then in February, it seemed like one of the easiest moves would have been to just trade Morris and throw a bigger burden on the young guys and see what happens.

He's expiring contract. Or maybe even get experimental and trade Kyrie and just try to get out of it and trade him to a team that could try to re-sign him. The arrogance of the front office on this one, and I really respect Ainge and Zaire and everything they did this whole run, but I thought it was a little arrogant to think that this was just going to get fixed with everybody being the same.

Why do you think they stood pat? Well, there were a couple of reasons. One thing I said over and over again in having conversations like this as the deadline approached was the Celtics were in position to add, have the biggest addition of anybody in the league and that was a healthy Gordon Hayward and it's funny because it kind of played out that way this his performance in the last few games was puzzling because he had been his most consistent and not even close over the

last two or three weeks of the season so and he had really been the bellwether if you think about this season that the Celtics and they won 49, and they were sixth in the NBA in scoring differential. And isn't it funny how people are acting surprised by what just happened when that series was exactly the regular season for those two teams. Yeah. 2-8-T, it played out exactly the way it was supposed to play out. And the playoffs often do mimic the regular season far more than we like to admit, even though we say, oh, the regular season doesn't mean anything. Yes, it does. It almost always does, and it did in this case.

The Celtics were in that stretch, and it ended in February. We can talk about, in my view, what the one moment was where everything really started to turn. I think the bad start or the shaky start was predictable because of all the pieces trying to fit them in place and a rough early schedule. And then I remember

saying, 19-20 games in, they're about to go on a run and turn this early schedule. And then I remember saying 19, 20 games in, they're about to go on a run and turn this around. And what will forever be forgotten is that they did. They were 25-9 in the following 34 games. They had the best scoring differential in the league in that time. And they had done almost what you thought they would be. Although all we remember, you don't remember the wins. You just remember the Kyrie press conferences

and Jalen Brown and Marcus Morris barking at each other on the bench, even though they were winning. So the deadline is coming up in February. The Celtics at that point, up until about a week or two before that, had really been playing well. And Gordon Hayward had been trending upwards. So there was potential for this thing to actually be pulled out of the fire. And let's not kid ourselves.

A week ago, when they won that first game in Milwaukee, a lot of people were convinced that it magically had happened. So to have faith, it's easy now to say, why didn't they make a move? Back then, the potential for the thing straightening itself out still seemed to be there. So what was the one moment? You said there was a moment when everything turned. What do you think it was? I believe strongly it is not a coincidence that the Celtics

go on that crazy run and the nothing really the bad start didn't surprise me them going on the run didn't surprise me and being as good as they were

but the final third of the season did and you can trace things back to they win a game in Cleveland in early February. Then those Laker and Clipper home games happened. And those were the games that really started the ugly downward spiral,

even with the crazy, bizarre nights they have when they beat Golden State by 35 after that. Kyrie, advertently or inadvertently, and let's just jump forward to the cut to the chase, as they say, by making his declaration in September, whether he meant it or not, and I think he did mean it at the time, it was brilliant. And then it took it off the table. It was gone. I'm staying. And so it was not an issue as the whole season was going on. And on February 1st at Madison Square Garden in the shoot-around in a deliberate statement because he knew the question was coming because he was in New York. In an attempt, in my view, to go at the media the way a lot of players have this year

in those press conference situations, like, get off my back, I'm going to do what I'm going to do, he caught every Celtics fan and I think his teammates to some degree in friendly fire by making the statement that day, I don't know what I'm going to do. Talk to me July 1st. And the feeling around this team, particularly externally, was never the same at that point. And it really has gotten 3,000 miles away. You can feel it, but I can't tell you how ugly it is here right now

in the relationship, which the Kyrie-Celtic fan relationship was always going to be one of two things. Either he's going to be a beloved legend with his number going up to the rafters, or he has the potential, this has potential to be the greatest heel turn in our parlance. Heel turn.

One of the biggest ones in Celtics history. I think it's the biggest. And you think about the signature guys they've had. I mean, Dad, since you've had season tickets, Havlicek, Cowens, Bird, McHale, Parrish, Paul Pierce, Antoine Walker briefly. Reggie Lewis. Reggie Lewis.

That was a good one. Yep. And then you go to KG. Ray Allen, almost. Almost. Rondo, definitely. Pierce, obviously. Pierce, obviously.

Rondo, definitely. Yep. And then Isaiah briefly. Yep. And then Kyrie. most um rondo definitely pierce obviously pierce obviously rondo definitely yeah and then isaiah briefly yep and then kairi those have been the signature celtics of the past but i 45 years i i think you just made a great statement kairi had the opportunity to be a legend here and uh that for i remember vividly i was at the season ticket holder thing when he got up and everybody was cheering and he was going to be re-signing. Yeah. And that February statement, I mean, as a fan, I never looked at him the same way. Yeah.

And you felt like both of you, because you were both telling me different, funny, different text threads, like the crowd really doesn't like this team like they want to like it they're going through the motions of being like the good supportive Celtic crowd but the moment something goes bad in the game it just dies they were and part of that had to do with this season was doomed in so many ways but one of it was by the toxic combination of the expectation level, which was so ridiculously too high, and the performance, which was too low. But the fans, I'd never seen, and this includes 08, by the way,

I'd never seen Celtic fans anticipating a season more and in love with the team more coming off last year and excited going into this year. And the guard hand turned in midway through the season, too, everybody sitting on their hands at the start saying, alright, show me. Show year. And the Garden turned in midway through the season too. Everybody sitting on their hands at the start saying, all right, show me. And when they did, it was a season in which the fans gave more to the team than the team gave to the fans.

And what it was, and the reason fans are so upset is because for those who are deeply ingrained in the concept of Celtic pride and what it means to be, this team betrayed that feeling of being a Celtic. And that's what I think drove everybody crazy. And then on top of that, you have Hondo dies. You have, you have Heinzen who has to leave and then we have to worry about him, but then he's able to come back. Koozie's still kicking, but you know, he's 90 at this point. And you see just the legacy of this whole franchise. Andy Jick died,

but you're talking about a seven decade legacy with this team. And it, it does feel, I know people from outside, they're like, Oh my God. And I'm talking, bragging about Boston again,

but it does. I think that, I think certain franchises have this. I think the Lakers have it too. I think when you have, you know, six, seven decades of memories and generations of fans, there does come to a certain expectations with it when you're the best player. And it was weird that Kyrie never recognized that at all. Maybe that's just what his generation is like.

I don't know. And you know, my only caution here in this, you're talking about Twitter and social media and reliving everything we say. Yeah. I, we are speaking in the past tense, which of course is a logical thing to do. Now, while it would be the greatest heel turn in Celtics history, the potential, if he decided to go the other way and say, you know what? And I know Celtic fans don't want to hear this today, but if he decided to go the other way and say, you know what? And I know Celtic fans don't want to hear this today, but if he decided to go the other way and say, you know what? I messed this up. I'm responsible for it.

Whatever. I'm back in. I'm all in. The potential, obviously, that's fraught with peril in a lot of different ways, too. I think that's a no for me, but keep going. Well, right now, today, as we're talking today, it's a no for all.

Listen, I walk home. I walk to the garden. I live about a mile away from the garden. And on my walk home after game four, people are so angry at Kyrie, they're angry at me. Just because they can't scream at him. People are yelling at their cars, from their cars in the levered circle there, where the cops have them stop because of the traffic. And they're so upset.

They're yelling about get Kyrie out of here and one of the great, isn't it one of the great ironies is that Kyrie's statement to the season ticket holders. If you go back, if you wanted to go

super conspiracy theory, remember what he actually said? If you'll have me back. Oh, so that puts the onus on us. So if you want to, yeah, subverter film that and say, you know what? He knew this whole time.

It was all a conspiracy. Because I think one of the things today, when everybody nationally was saying, well, if this doesn't go well and this season doesn't go well, Kyrie's going to leave. They had in their head the notion of the players around him not performing and the season going down the drain and him looking for a better situation. Nobody had projected the idea that he would be a large part of the reason it didn't go well. And that the fans who four months ago, the notion they lived with the fear, the biggest fear among Celtic fans four months ago, six months ago is that Kyrie could leave. And now, if you polled them today, you'd get some amazing numbers

as to how many actually want to see that happen. But that's why you don't make decisions the day after the season ends. That's very wise words. And I'm going to heed them for about three seconds. He can't come back. He can't come back. There's too much damage.

This is now a relationship where there's been too much damage. And I don't think the fans are going to trust him again. Because guess what? We went through it after the trade deadline with the whole, hey, they figured this out in the plane ride. Kyrie fell on the sword. He admitted he was a dick.

He's going to be more of a leader now. And then he walked the walk for three weeks, and then it stopped. It begs another issue. Would, do Danny and Wick and Brad Stevens, they want him back? I would say.

I think, you know, there's going to be a public answer and a private answer. I think we're all in agreement for the most part

that the Celtics signing him is still the, you know, gives you the most options. You know, it's still the best situation, you know, whether it's sign and trade, whatever it is,

him walking still leaves the Celtics in a, in a bit of a problem. I don't think there's any question about that. Well, so the sign and trade, so they, there's two separate conversations. One is that, can you still build around Kyrie? I like the, I like the sign and trade. Well, that's the other thing is like, he's still an asset, even if it's a sign and trade well that's the other thing he's still an asset even if it's a sign and trade and it's a situation

a little similar to what the Rockets were able to get with Chris Paul the only thing is I think they changed the sign and trade rules isn't it harder to do a sign and trade now? it is harder but it's still a better for the Celtics to have control of his contract as we enter. And the Celtics just entered the party room last night of what we all know

is going to be the wildest, most insane off season in NBA history. And I don't know what dependent races are going on. I think we say that every year. I don't know what's, what stories are going to come out of NFL training camp, but the NBA is going to own the month of July. Like it never has.

Well, the rumor, the rumor mill is fantastic. I don't mind passing along various things I've heard, including somebody told me that Ty Lue, the Lakers had to back out of the Ty Lue thing because Ty Lue and Kyrie, they couldn't be together again and Kyrie's going to go there. And that's why that fell through, not because of the contract. I have no idea if that's true or not, but that's going to be the next two months of my life. It's like, wait, is that true?

And then I'm texting people trying to figure out, wait, did Ty Lue and Kyrie not like each other? But maybe there's a world in which they sign and trade Kyrie to the Lakers for Lonzo Ball or something. By the way, sign me up. I'm in. I'll drive both guys to the airport. Wait until Golden State and Milwaukee are playing in the finals,

and Kyrie and Kawhi Leonard are sitting next to each other, or they're seen together across the street at LA Lot, or all of the, I mean, we have not even begun to scratch the surface. It's going to be great. And you're right. The stuff leading up to it is going to be better. Then look at KD and Kyrie having that conversation on the wall in Charlotte. Right. All-Star weekend. And what did that become?

Yeah, we have just, you know, the social media is the fuel of the absolute. If you love this stuff, if this is what you love about, you know, we always talk about the Monday night raw used to be wrestling and now it's all the interviews and the crazy stuff, whatever. And that's what people like. You like this stuff. You're going to love the next two months. And it's going to keep going and going. I mean,

the other thing with Kyrie beyond the whole personality standpoint is he's 26 years old, about to be 27 at an age where point guards, I think have, you're talking maybe 10 to 12 years before they kind of morph into a different part of their career, which we're seeing right now with Chris Paul. And he's had a lot of injuries already. And he's had some guy who's had knee injuries and knee surgeries and five years, 220.

You saw what's going on with Washington and John Wall right now, where if you miss on that contract, you're screwed. That's it. That's it. You're done. You're done completely. Is Kyrie, is this who he is going to be? I brought up this example because obviously we're just, we've seen

Kyrie and the way he is throughout his entire career. What teammates have said about him, what players around the league say about him. We all know what it is. And chances are that doesn't change. And you are who you are. But in Boston, I use the example of Paul Pierce who did not

have a good reputation in the league. And earned it. Earned a bad reputation. George Carl, 2002 World Championships. And then you guys remember, Celtic fans remember in 2005, he had like a hissy fit during that Indiana series. Yeah. Gets kicked out of game six. Remember the Jacob Marley bandage around his head?

Well, here's the punchline of that. Paul Pierce was older than during that series than Kyrie is now. Yeah. Yeah, Kyrie is. There's still potential for it to be different. He can still change the trajectory of that other part of his game. He can do things on the floor that nobody else can do, but he has not figured out the other part yet.

He is swinging and missing at his notion of leadership. I believe his earnest. I think he actually believes what he was doing this year was leadership. He just, it's like that Facebook commercial. That's not how this works. That's not how any of this works. You're doing it wrong. Do you think Tatum, Brown, and Revere think that his version of leadership?

I don't think they thought it went very well. I think they'd drive him to the airport. And then poor Al Horford was like the mom in a 1950s movie, like where the dad is. Isn't it funny? And, you know, that's why Al's the perfect player. He's like, he can play with anybody. He can play in any situation and he's still going to do what he does. I find it fascinating that Marcus Smart, who, if he's not your favorite Celtic, maybe he

should be. And in so many different ways, Marcus Smart loves Kyrie. Loves the dude. And it's just funny how certain people get along with certain people. And, you know, Marcus Smart today was very quick to shoot down all this idea that kairi was the problem but it was it was you know our our friend colin cowherd said yes he said it exactly right that you look at the players around kairi this year did he make them better or did he make them worse and this was a year in which a lot of guys took a step back. And on the one hand, it's completely unfair to throw a lot of this on Kyrie.

On the other hand, this is what he wanted. Yeah, it's not unfair because he demanded this. He wanted to go to a really good team and he felt like he was a superstar. And by the way, I agreed with him. I thought this was a great trade. I really, I was like... Everybody did.

And by the way, Isaiah Thomas, I mean, nobody would not. Everybody did. And by the way, Isaiah Thomas, I mean, there is, nobody would not have done this deal. Nobody. And that was without not even knowing that Isaiah wasn't going to play. Although his team is still playing and Jarebko's team is still playing, which is kind of funny. I'm a psycho, so I'm just going to, you know,

I have weird karma stuff. And I think about, I do think about karma a lot. We shouldn't mention that from the moment they made the Isaiah Thomas trade, the karma swung against this team and continued to swing against it. And I do think about that. And I do wonder, is that just a coincidence? I think one of the things that underlined it, during that post-February 1st, I think one of the things that underlined it during this,

that post February 1st, and I strongly believe that moment changed everything. It didn't get, no one like media here doesn't really talk about it. I just, from a feel standpoint, yeah. From being around the team in the building,

I felt that moment was very significant. And one of the things that came after it was the night that Isaiah came back and finally got his, you know, got his video tribute and whatever. And obviously it was a night that Isaiah came back and finally got his, you know, got his video tribute and whatever. And obviously it was tough time for him and all, but he, that was such a natural love affair and fans tried to transfer it to the, to the new guy, the hotter girl, right? The brilliant, brilliant Kyrie. What this whole thing was, was the Celtics landed the, you know, the runway model and said, oh my gosh, we got, look at what we have here.

We did this. And you heard the stories, right, about stuff from previous relationships. You heard some behavior. But you know what we all say when that happens? That's not going to happen with me. It's not going to happen here. And obviously Kyrie was, has been the same guy and it's unfair. I think it was unfair of us to expect him to change and expect him to be different. Kyrie is who Kyrie is. So you think this was like when Springsteen married Julianne Phillips,

but then realized he should be with Patty Scafio? That wasn't the first one that came to mind, but I think that probably works. I remember when I was a kid, when I was in high school or junior high school, I was growing up in Manhattan. I looked out the window and I saw the boat going by the East River that had Billy Joel and Christie Brinkley on it. Yeah. And you thought, oh my gosh, it's perfect. It's going to last forever.

I've told a girl. Yeah. Yeah. Were you on the plane during the famous cross-country trip with Kyrie? Were you on that one? I was not on that flight. But I do remember, you know, I was talking to everybody who was on it, and I had a flight separately the next day.

I think that stuff gets really – the flight I remember, the only flight on which I celtics hit the only flight on which i remember celtics history genuinely changed with the flight after game seven in 2010 where when we got on that plane that everything was breaking up doc was leaving kg was like that whole thing was done and i think in that six hours back everybody talked themselves into one more run and it started with doc and kg came back and then they added Shaq. And it's funny because we talked after that following season, which played out very similar, kind of a bad ending.

Easy first round win and then get bounced, you know, in the second round by a team that, listen, it's not, you didn't call me to talk about the Milwaukee Bucks, but forgotten in all of this, Kyrie this, Kyrie that, Celtics are a disaster, gone fishing, Kyrie on the road, all of it. It's all fair, and that's the way things are. The Milwaukee Bucks have been the best team in the NBA all year, and it's not even close.

For seven months. They're unbelievably good, and they've got a real shot to win all of it. I couldn't agree more. And they have a great player and really good bench guys, and they're well-coached. And they have home court, by the way. Home court batters. I know it's one game. it's silly, and it's one game, whatever, but these final four teams in the East, now final three, they all won their game at Oracle

this year, easily. So, you know, more little cracks in the cement. That's the real NBA story here going forward is, do the Warriors have one more? Can they crawl, you know, you know NBA history better than anybody maybe in the world. These dynasty-type teams, when they get to that last one, 98 bowls, can you cross the finish line one more time against the usually young, hungry? Because you're not getting Glass Joe in the finals again. You're going to get a real team,

even if Toronto finds a way with Kawhi playing at another level. This is going to be a real final this year. I agree. How would you compare Kyrie around the Celtics team to Eddie Edelman in the 15-10 offices in 2002? There is going to be a time people are already calling about that question.

There's going to be a time in history when we look back at the people that were there at that time. Actually, there's going to be already an in history when we look back at the people that were there at that time. Actually, there's going to be already, I think, an oral history on this ill-fated second sports radio station in Boston, in which I recruited you to be a part of it. A guy by the name of Ryan Russillo has done fairly well since then. Yeah, Sean McDonough. Sean McDonough, Michael Hawley.

He did a lot of stuff nationally. I mean, we recruited a lot of people to that station, and that was a time when you had to add a, you needed a name, right, at that time. And so that was the thing to be made at the time. So your prediction is, is Kyrie on the team next year or no? I, you know, listen, today everybody says no. I just don't think you make decisions today.

If you're Kyrie, here's the thing. Where are you going? Where are you going? What is it you want out of your life? Do you want to win basketball games? And if you don't, and by the way, the Nets thing, if the Jalen Brown, Terry Rozier, Jason Taven thing didn't work, how's the D'Angelo Russell, Karis LeVert, Spencer Dinwiddie thing going to work in Brooklyn?

In New York, there's 10 members of the media asking you questions you're too sour to answer for everyone there was in Boston when you go to New York. In L.A., the same thing. It only clearly works for him if he's got, you know, what's Durant going to do? And by the way, talk about a sullen, dour double play of Kevin Durant and Kyrie Irving as the face of the franchise, as good as the basketball is going to be. So all of a sudden, look at the Celtics right now and say, should Jason Tatum be better next year? Should Jalen Brown be better next year? Should Gordon Hayward be better next year?

Terry Rozier, I mean, Terry Rozier, if he comes back, which is not likely, but if he did, he's almost definitely going to have a better. The best basketball situation and the best money situation is here. The question is, can he repair the damage with the fans and whatever? And while the answer today is no, let me tell you something. On July 1st, if Kyrie says, my bad, let's do this thing, I'm staying. Celtic fans love this team and want to win so much. I'm telling you, I saw it this year.

You said it yourself. How many times did you get sucked back in this year? Because they kept bringing you back in all the way through game one against Milwaukee. If Kyrie says, my bad, let's do this thing, I'm telling you, everyone's going to give him another chance. Dad, the worst case scenario here is they sign Kyrie to a one-on-one and then they trade everybody

for Anthony Davis and they put all the eggs in the one year of Davis and Kyrie basket and then they both leave a year later and we have nothing to show for the last decade. I'd never do a one year with Kyrie, but I hate the thought of him leaving and us not getting anything in return.

Yeah. I don't know the sign and trade. I guess he would make more with the Celtics if he signed and then we traded him. What about, are you worried at all about Al Horford leaving? I am. Because he can opt out of his contract. I hope he does. Pretty significant.

Pretty significant, yeah. What do you think about that one, Sean? I think it's a little concerning. I think his relationship with Boston and with his team and with Brad Stevens obviously is much better. I think he wants to see what's going to be happening here. I think the biggest concern, and Al Horford, I've said this many times, the fascinating thing about it is, from a human standpoint,

you'll never find two people more different than Al Horford and Kevin Garnett, but on the floor, although Al Horford is not one of the 25 greatest players in NBA history, and it's an unfair comparison in a lot of ways, he does so many of the things that Kevin Garnett did when he was here and he can do it without having to be the superstar and gladly taking that back role. So he's the perfect Celtic. The, my own, the only thing about Al Horford is you've got to put on your,

your Danny Ainge harsh reality hat when it comes to his age and his miles and things like that. How many more years of Al Horford playing at this elite level are there left? That's a legitimate question, but you need Al Horford next year. You need him. There's two issues. One is it's an Al Horford player option, not a team option. Right.

The second issue is if he opts in, it opens the door for a Davis trade. He could opt in and then it could be like, yeah, cool, Al, you opted in. Great. Hey, you're going to New Orleans. I mean, he saw what they did to Isaiah Thomas. It's not like he's ever going to trust Danny. Would you trust Danny? Nobody, you can't, Danny can't be trusted.

He'll trade, as the saying goes, he will trade anybody on any day. He does not care. He would trade his son. He would trade his son to like OKC for a first round pick. So. I mean, he would trade like, you know, Doc would trade, Doc would. And they both traded, you know. Yeah, Doc did trade his son. And he both traded his son to like OKC for a first round pick. He would trade, like, you know, Doc would and they both traded, you know, Doc did trade his son.

So, if you'd be like... There's no question about it. And, you know, Dan, this formulated, it's funny how people, you could always trace back people the way they are to something that they went through and something that happened. And Danny watched as Red let the Celtics get old. And he would ask him about it. Because they had that kind of relationship.

He would, he was encouraging them to make the trades, trade Larry, trade Robert, you know, at the time in his career, he was doing it because he saw it coming and you know, he swore never again. I'll never forget when my dad and I found out that we could have gotten shrimp from Perkins for McHale for one legged McHale. Yeah. But you, I was in the camp of, we should have done it. And you,

my dad is such a loyal person. Well, I was like, we can't do that to McHale. I was, that was your, you were against it. I was at the February 87 game when McHale got hurt.

Yeah. And he kept playing, played through the playoffs. You were like, we can't, he did so much for the team. Yeah. But in retrospect,

that would have been an unbelievable trade. I'm glad we didn't trade him either. That's why Danny's in the job and we're not. Early 90s Celtics and the 80s New York Islanders. Exact same deal. Dynasty teams that the general manager could not pull the trigger on getting rid of the guys that were so loyal and had won all the titles. And then decades of ugliness followed. Now we're never going to have teams like that again,

because everybody just switches teams every four to five years. We're never, Steph Curry is going to be the last guy. And every, and every week they're, they're taking pictures with guys on the other team and, and you know, I don't want to get into this, get off my lawn, AAU mentality, but isn't it interesting that the best player in the league now did not come from that? Yeah. AAU American basketball all on the same team mentality.

I think it's interesting. I like that point. I'm going to steal that. Wonderful play to watch play basketball. I stole Grandy's. Hey, can we establish this thing now? I got some pushback on Twitter. I thought I had come up brilliantly with this idea of. You did. I stole Grandy's. Can we establish this thing now? I got some pushback on Twitter. I thought I had come up brilliantly with this idea of.

You did. I gave you credit. No, I, and I'm sure that you did. I just didn't, I wasn't sure. I didn't know if I had lost my mind when I came compared to sell it.

Cause we got inundated during the tournament with that commercial. If it wasn't, you know, it wasn't Charles Barkley and Samuel Jackson, by the way, I do, I have to ask a question here as an aside. Yeah.

Charles Barkley has offered to throw me a bachelor party for my wedding coming up in September. Is that an extraordinarily good idea, or is that an exceptionally bad idea? I think it's both. That's a question I'll throw out there. Let's ask Nefi Kyle. Nefi Kyle, should he?

Do it, do it, do it. Yeah, Nefi Kyle's in. Nefi Kyle's 25. During the tournament, we're watching the commercial, right? It's not them. It's for orange vanilla Coke. When people asked me about the Celtics this year, I said, do it. Yeah, Neficazen. Neficazen's 25. During the tournament, we're watching the commercial, right, and it's not them, it's for orange vanilla Coke. And when people ask me about the Celtics this year, I said, you know what?

Orange is great. Vanilla's great. Coke is great. But maybe all three of those great things together do not make a great drink. And that was what the Celtic team turned out to be.

It was the best analogy. I stole it, but I credited you every time. I'm mad that anyone on Twitter... You never know anymore, right? It'd be so hard to be a comedian now and to write monologues and whatever because it seems like every time

you think of something funny or whatever, somebody must have already thought of that. What's funny, though, is I got the... How do you check? I got it wrong, though. I just thought it was vanilla Coke. The orange vanilla Coke is actually better for the analogy. Yeah.

That's the only thing that made me think of that was because of the, when they kept coming up with the new, we have to invent the new thing. So Coke was Kyrie. Orange was all the young guys. And then vanilla was Brad Stevens and Horford. And it all just seemed like it was going to make sense, but it just didn't. Oh, well.

Well, at least you get some time off. That part's fun. You don't have to work anymore. Well, most people would not consider what I do to be working. You don't have to travel? Maybe this year more than other years. You got your bachelor party? You get bachelor party to do?

Sean Grandy, a pleasure as always. And thanks for coming on. I know you have seven more radio and podcast hits to do, but Grandy, a pleasure as always. And thanks for coming on. I know you have seven more radio and podcast hits to do, but thanks for making time for us. Excellent interview. Hey, two generations of Simmons. It was my honor as always. Thank you.

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Let's just leave it there. Hurry into your local BMW center today. Test drive the all-new BMW 3 Series for yourself. I rarely say stuff like this. They're the best at making cars. I really believe that. I think they put the most care into their technology. And it's just my favorite car to drive.

The all-new BMW 3 Series. Don't be driven by technology. Drive it. BMW, the ultimate driving machine, and they ain't lying. All right, let's bring in Jessalyn. So this is the second time we've done this. Anthony Jessalyn is here.

Grantland, I'm going to say like 2013, maybe you came by? Yeah, I went in 2013. Somewhere in there, 12, 13? Yeah. This one's going to be a lot easier because you won't be as nervous. You know, it's like the second time around. It's a great point.

I was shaking. Yeah, I was excited to have you on the last time. And I think I pursued you as a guest, which I don't normally do. Probably. Normally I have third parties, but that one, I was like, I need to get Jocelyn. I got to dive into this guy. Yeah, I was psyched. They even knew who I was. Yeah. I ran into Kimmel a few weeks ago. one i was like i need to adjust like i gotta get dive into this guy yeah i was psyched they even

like knew who i was you know like i ran into uh kimmel a few weeks ago and he just quoted one of my tweets to me word for word and i was like that i was shocked like and he was like oh yeah bill and i yeah and i like screenshot back and forth your tweets all the time that's not that's not a lie yeah me sal jimmy and, and Daniel Kallison, my old producer there, every once in a while you'll have a tweet. And we have this text chain that if anybody ever hacks it,

we're all done. But sometimes you'd be like, man, fucking Jesselnik still doesn't give a shit. It's the best. That's how I know. Everybody gives a shit now. You're like one of the five people left

that just does not care. I'm the last guy. I think you can do it. But I know I might be in trouble when someone texts me great tweet when they don't like retweet it or comment on twitter they just text it to me i'm like oh you can't endorse this but you think it's funny it's like stealth exactly stealth praise yeah yeah i feel that way about almost all your tweets yeah pretty much i'm like i'm not retweeting this but i fucking loved it every day before I send any tweet

my thumb hovers over that send button I'm like hmm and I almost always 99% of the time hit send and then it's like let's see you really don't know I used to be there and around 2012 I just couldn't do it anymore

because the fear of the backlash and the problem is when you're doing tweets like that and if you go back and read I just couldn't do it anymore. Because the fear of the backlash, and the problem is when you're doing tweets like that, and if you go back and read, like, my tweets in 09 and 2010, it's like you're just firing them out. And some of them hit, some of them don't, but you don't know. And we've removed that, I don't know, that adventure, adventurous nature of Twitter where it's like,

I don't know what's going happen here nobody wants to find out anymore it's become a press release you know and I worry that's gonna happen with podcasts there's gonna be a way you can search podcasts for terminology

and start getting people that way because Twitter it's easy you just search like certain keywords on Twitter and you can find everyone's everyone's stuff but podcasts you can't

and people say some wild shit on podcasts that it could be the next frontier. Especially the longer ones, about 80 minutes in, I start to get groggy. That's when the weird shit starts coming out. Exactly.

Weird basketball opinions. You start going, Chris Paul's a loser. He can't win. Then you're like, whoa, did I say that? Why did I say that? I I say that I walked out of I did Joe Rogan's podcast the other day and it's like three hours yeah let's hear about that

and what does he do he like tries to wear you down what is the methodology on that it's different with me because I'm a comic that he knows you know we see each other

almost every day at the store so it's a different vibe than if he's trying to really get something out of someone and I was like I don't really remember saying anything

edgy or controversial or anything and then I see like a blog the next day being like, Anthony Jesselnik calls Jerry Seinfeld aggressively corny. And I'm like, yikes. I did not remember saying that, but I guess I did. That's the thing. And this really worried me with podcasts once mine started to take off during the Grantland days like people can pull stuff out of context in a conversation and it doesn't account for tone no it doesn't account for can you hear in my voice i'm joking as i'm saying it or any of that stuff what the what the context of the whole conversation was and they could just pull out the little tidbit yeah and

that becomes the thing i think people are wiser to that what's weird is this is one of the few benefits of the trump presidency i feel like where um people are actually more suspicious of things like this now absolutely we're in a new era where people are like wait a second are we sure that yeah that doesn't pass the smell test and they'll at least kind of examine it for a second it's crazy i mean even where that's going with like the deep fakes thing you can like make someone's face yours and do a thing that like every video is going to be suspect pictures are already suspect yeah uh but people still believe in jesus you can't fake comedy yeah jesus and comedy yeah yeah yeah that's that's i read this whole story i think it was on like wired one of those places about deep fake porn so this is like

the new frontier and these people spend days putting like emma watson's face on some porn actress and then they put it out there like it's her well i've done that like i took like scarlett johansson and put my face over hers and then i use that you know i mean it's it's hot as hell that's really good. That'd be pretty creepy. Yeah, super creepy. I haven't seen one that's not creepy, but when they're well done, they can be funny. How does Kyle Dunnigan do the Instagram stuff he does

where he's doing some sort of, it's not a deep fake, but he's blending something. I think it's just a really good deep fake where he also does the impression. It's like a deep fake done as well as it possibly can be. I think those are great. It's super creepy. It's really good.

And it's also like kind of haunting. But it's like where Jordan Peele did that commercial, like warning you against deep fakes where he's doing Obama's voice. And it looks, it sounds exactly like him because it is, it's like four dimensional. You know, if you can do the voice too and the mannerisms, you can do a great great deep fake but if it's just slapping an actress's face on a porn star's body you can kind of tell you know so you're in the i'm catching like the tail end of your press tour for your netflix special it's honestly a never-ending press tour now with netflix because you can see it forever so it's almost it used to be like two weeks out start promoting now that's

worthless because everyone hears netflix and they want to go watch it right away yeah so if you're in a day early it's a waste of time right so you had one in what 15 uh for for them for 2015 yeah 2015 and now this new one what did you learn from the 2015 one that surprised you because you think think about the history of the TV comedy special. So it goes back to you're talking to HBO early. That was when comics wanted to get on initially. Either on the Young Comedian special or maybe get an hour

or whatever. Then it became Comedy Central half hours, maybe possibly an hour. Then it kind of shifted back to HBO and Showtime. And now it's this whole Netflix era where it pops out of nowhere and people can see it in like 175 countries. I mean, it's changed everything. It's so weird that this is my fourth hour of firing the maternity ward. When I went on tour after Thoughts and Prayers, that's when I noticed.

You know, you see stuff on Twitter. Yeah, when that came out in 2015 and then I went on the road all of 2017, all of 2018, and you just saw a much bigger audience. Not only that, but if I would mention older work, like if I mentioned Caligula or Shakespeare, which were my first two hours that were on Comedy Central, no one knows what I'm talking about. Really?

Like in Thoughts and Prayers, when I talk about my Comedy Central show, most of the people who are watching it don't know what I'm talking about. Really? Like in Thoughts and Prayers, when I talk about my Comedy Central show, most of the people who are watching it don't know what I'm referring to. Because I never say Comedy Central. I never say the name of the show. They're just Netflix people. And they really don't.

Like people keep calling this my second special. I'm like, it's my fourth. But it may as well be my second. Is it almost be smart for Netflix to buy the other two and just put them on there? So when they searched you they all came up like the first one was an album the second one caligula was a special and i really wanted that to go to netflix when netflix blew up and comedy central and netflix are at each other's

throats yeah neither one wants to help the other in any way every comic wants their stuff on netflix even when it's older and comedy central will not budge people like jimmy carr was like you should re-record your first album, Shakespeare, as a special for Netflix. And I'm like, that material is 10 years old. Like there's no way I want to revisit that. And that's a big 10 years. Yeah.

Late 2000s, people were still crossing the line. Actually, 2010. So yeah, that's when that came out. It just, it would feel, telling an old joke to me just feels stale coming out of my mouth that I don't want to do that. Unless you're Jerry Seinfeld. I don't know out of my mouth that i don't want to do that unless you're jerry seinfeld paycheck i don't know i'm kidding i don't know how i know listen i love seinfeld i've never met the man but his movie comedian the documentary changed my life to the

point that i consider the day that movie was released to be the day i started doing stand-up but i just i went to see a show yeah yeah it just told you everything you had to know as someone starting out who was like scared to go to an open mic that movie showed seinfeld having to go to an open mic having to go and deal with like having no material and building but it was just like oh you just do what he did and if he can go through it then i can't you know if he's that big then i can i love that special never met him the new one the one where he kind of goes back and revisits no I love the comedian

oh comedian yeah that movie I watch it once a year I feel like that was before it's time because if that came out now it would be a much bigger deal

yeah because you would be able to push it better I forget what channel had it was it Comedy Central no no it was a movie it was a movie

in just a couple theaters and then you rented it it was like back in the rental pay-per-view days it was one of those where you couldn't it wasn't even streaming forever yeah you had to buy the dvd on amazon or something now it's on netflix but i think if it had just debuted on netflix today it would be huge it'd be huge i think i mean i saw seinfeld twice in the 80s the talking like because he was like one of the original Letterman guys he's been doing it

for 40 years I think when when you hit like your 60s and you've been phenomenally successful I don't understand part

a lot of comedy comes from you know either self-loathing or you're mad about something or there's some sort of conflict

that it's coming out of and if your conflict's been removed from your life, I don't know how you do comedy. That's a tough thing. Like I ran into Chris Rock and I was like, what are you working on standup wise?

He was like, nothing. Like I was on tour with him for a while. He was like, I'm doing this special. And then I Netflix another one. He's like, maybe this summer I'll start working on the new material.

And I see him, this is a year later. And I'm like, what are you, what have you been doing? He's like, nothing. He goes,

I'm too happy. Yeah. I'm too happy. Yeah, that's true. I'm too happy to be working on Santa right now. Is that death for comedy? Yeah, it really is. Like right now, I should be working on the new hour right now, but I'm so satisfied with this last one that I'm like, I need to wait till that wears off.

Victory lap. Exactly. I need to wait till it wears off to go out because I'm so proud of that, that like going up and bombing with new material is so unappealing. But at a certain point, I'll be like, no, let's go. I need this.

Your manager should have paid some writer to do just total hit piece on the special. Get your juices flowing. That would have done it. That would have done it for sure. This piece of shit. How do we keep allowing this guy? Yeah.

You'd be like, what? I keep waiting for something to happen that'll tick me off. People are afraid of you now. Yeah, but usually still something makes me mad enough that I'm like, I'm going to go prove everyone wrong. And I haven't found that yet. So this is a compliment and an insult.

Maybe this will get your juices going for the next special. Please. You're the greatest roast battle judge of all time. Thank you. It's a compliment and an insult. I don't see how it's an insult. Okay. I think, why would it be an insult?

Well, it's my favorite show, so. I mean, that's an insult to you, I think. Like you should have better taste in television. But that's my favorite thing in the world to do because you can't prepare. And you're just sitting there for 10 minutes and all you have to do is just one killer joke. And I could see your brain like just percolating for and then it gets

to you and you're just like ready yeah i'm so excited and like the work i put into doing a roast is is infinite compared to the work you put into doing roast battle roast battle you just show up but the roast is like months of banging your head against the wall looking for the best possible joke. And the roasting, it's like we had too many of them. It became like professional wrestling where the guys kept going higher and higher to jump off whatever ladders, and then it was like a scaffolding. And then it's like at some point, the only way you can really shock me is to jump off like a 50-foot five-story building and do a belly flop on somebody. At some point, there's no more line to cross.

Yeah, I really feel like they peaked with Charlie Sheen. Like I did Trump, Sheen. Trump, it was great. Sheen was great. And Roseanne was like, it didn't matter. Like I remember doing a club the week after the Roseanne roast and it was like half filled. And I was like, I can't believe this. I thought for sure it would just be packed

and people just didn't watch that roast. And now it's just gotten very hard to book them. You know, Twitter changed things a lot. People get real-time reactions. And I agree, people have just gotten meaner and meaner and you don't want to bomb either. Well, it's also people being mean about somebody they've never met.

And I don't know, you know, the early days of Rose, it's a big good oral history book, but like the ones that I fell in love with, Shaq used to have those comedy Rose. He had a famous one. Was it the Emmett Smith one? He had two. The first one was with Shaq.

It was just on Shaq and Jeff Ross. That was when I fell in love with Jeff Ross. He just like completely crushed it. It's an all black audience. He just in love with Jeff Ross. Yeah. He just like completely crushed it. It's an all black audience. He just comes out like just firing. Yeah. And it was great.

But one of the funny parts was like half the people didn't know what a roast was. So you had people who got invited and they thought it was like a- A tribute. Yeah. Yeah. So then he had the other one with Emmett Smith and Moose Johnson, the fullback for the Cowboys was up. Did he throw a chair? No, he did a roast, but he didn't do a roast. It was like a speech. Like they were at like the...

About like what it meant to be a cowboy? Yeah. So Jeff Ross followed him and he goes, sorry, Moose Johnson did all my shit. Like he made one of those jokes. Moose Johnson's like, what? Like you insulted me? Yeah. And now everybody kind of knows what a roast is. The early 2000s, it was still, you could sneak it by people like Moose Johnson.

Yeah. Yeah. But still, I think when you do the private ones, people, it's a bad idea. The private ones, what are those?

Like with someone's like, it's for charity or my friend's birthday party. And I rarely get invited. I always turn them down because i'm like you really don't want me there you don't you don't want it have you done one of those never i've only been invited to like two they have them all the time but i'm like the last guy you would want like that's one of the reasons i stopped doing them was because they

did the franco roast and they were like they they don't want you and i was like why i kill and they were like, they don't want you. And I was like, why? I kill, and they were like, yeah, but as of right now, we've got Natalie Portman, and Kate Hudson is on the day. I was like, we don't want you going after them. And I was like, I kind of see your point. These are like Hollywood princesses, and they ended up bailing anyway and not being a part of the roast.

But once they kind of said that, I was like, you know what, I'm not going to get nicer. I'm not going to tone the sound. I just have to be able to ramp it up. Like you said, like how high can you go before it's just a complete atrocity? The saddest roast was the Chevy Chase one. Were you at that one? I wasn't at that one.

I don't think I was even doing comedy when that came out. But that is one of my favorite roasts. It's a total shit show. It's an unbelievable youtube extended clip or whatever you have to find on youtube like when i did the my first roast i was like comedy central give me all of them so i can watch them all and then we've got everything except the chevy chase roast i'm like what do you mean you don't have it and then i look it up on youtube like we destroyed it like it's oh they destroyed it oh they i mean because they never wanted to rerun it it was just a it

was a to them it was, to them, it was a fiasco. And that was the one where like, they took it from the Friars. They did it themselves. And that's why I love it so much. It's like, it's Todd Berry. It's Andy Kindler. It's Stephen Colbert, people who you'd never think would roast doing their version of it, but to a completely disinterested and hurt Chevy Chase. Who from five minutes in, his feelings were hurt. He wasn't selling the jokes anymore. And from five minutes in, his feelings were hurt. He wasn't selling the jokes anymore. And it was the worst three hours of his life.

Now, I mean, being roasted is an art unto itself. Yeah. You know, if you sit back and throw your head back and laugh every time someone makes a joke about you, you're the star of the roast. They keep cutting to you. But if you just sit there with your sunglasses on looking ticked off, then everyone's just awkward.

That's why Shaq was so great way back when. Yeah. Because Shaq has great reactions. Like you want people reacting the same way they would react during the dunk contest or something. Oh, totally. Throw their arms out, kick their head back. Yeah.

Yeah. I mean, imagine if like, remember the Flavor Flavor roast? Oh, yeah. Imagine if Flavor Flavor thought those jokes were racist and they were all racist, but he didn't think so. Like if he had just sat there and been like, how can you say that to me? What? That roast would have been over quick. Flavor Flavor thought those jokes were racist and they were all racist, but he didn't think so. Like if he had just sat there and been like, how can you say that to me?

That roast would have been over quick. But he laughed so hard at every one that it was great. When I was working for Kimmel, he was the emcee. I think it was Courtney Love. Is that possible? It is, right? No, Courtney was on the dais for-

Oh, it was Pamela Anderson? Either Pamela Anderson or Shatner. It was Pamela Anderson. Yeah. And it was a much longer day. I actually took house. It was in the other room. It was like three and a half, four hours.

Because you see the edited version, but you don't see, you see like the best parts of everybody's roast, but it's actually like twice as long. Yeah. And it drags in some points. Oh, for sure. And if you have somebody who's bad and it's not going well early,

it really feels like it's an hour. But that's what they used to do is when they would show it on TV, like before they went into commercial break, you would see like the guy who played Big Pussy on The Sopranos like saying a sentence as they went to break. And you were like, oh, I guess it didn't go well.

Or he just told a story. Definitely not. But now it's like people in the theater tweeting like Big Pussy's bombing, you know? So they've got to show it after that. Did you it's like people in the theater tweeting like, the big pussy's bombing. So they've got to show it after that. Did you ever hear about the ESPN roast that they did once? They did one for Mike and Mike and all tapes were destroyed after. I wonder how many times that's happened.

Oh, I think anytime they've taped it, like 90% of the time they destroy the tapes. Can you think of a worse idea than ESPN, who in the mid-2000s was pretty humorless, as I can tell you because I was working there yeah being like you know what to be good or roast and and alcohol I can't go wrong I can't believe they even had alcohol I mean Stuart roast like after the Norm Macdonald Espy's you know monologue yeah they were like another great moment in your life huge love that and I just thought that's how these things go like oh what how amazing I didn't think like

Norm's breaking the mold it was like this is how this is but when jimmy kimmel hosted a few years later i wrote some jokes for him and so did i in his contract he was like you can't i get to do what i want and then they cut my jokes oh i had like two or three jokes that they cut out of before it went to air and kimmel was furious and then printed the jokes so like my jokes got more traction than they would have if he had actually said them but he was like I'm never doing this again I can't trust you well the good thing was I was directly in the middle of that because I was the one promising him it would go okay with the ESPN yeah like they cut his monologue from like eight minutes to four and as i was watching it was like and and people

always say this but this really was true like i would say he got like five really huge laughs like big just jokes that just crushed and i think all of them came out so it's the combo of being edited but then also like what they edited made me less funny he was he was out of his mind and this is what i had been complaining to him the whole decade. I was like, nah, the fuck fucking took three jokes out of my draft diary. And so he would hear it.

He, he'd been hearing it from me for years, but that was way worse. What happened to him? Cause he knew in the room he had done well. Well, a place like ESPN, they don't need humor.

You know, they like it. They like the idea of it, but they're like, I've done some work for the NFL network and they're even worse. they're like don't you dare make a joke and if you do it better be about like clowns or something because you can't make fun of these athletes so when you're at the espies and everyone you're making fun of is in the audience they're not happy like they used to do they used to hire a comedian to host the porn awards yeah like the av the adult video

uh awards and And every year, the comic just completely bombed because they're making fun of porn and porn stars to an audience of porn stars. And they have no sense of humor about themselves. First of all,

you act like I didn't watch that every year on Showtime. It was always the best 10 minutes of the year from an unintentional comedy point. I used to fantasize about it until it got to Showtime. I was like,

well, if it's on Showtime, how good this really be you know but a bit on like if you gotta like if you gotta buy it for 99.99 on pay-per-view i would have done it every year it's like ron jamby's in the house yeah a lot of that it was great someone i'm uh i a porn star on twitter got in touch with me and she was like hey uh do you want to come to the porn hub awards this saturday and i go oh porn hub awards yeah is that a thing i guess it is now i think it's a porn star on Twitter got in touch with me and she was like, Hey, do you want to come to the Pornhub awards of this Saturday? And I go, Oh, Pornhub awards.

Yeah. Is that a thing? I guess it is now. I think it's the first year, maybe second. Great. I was like, Oh,

I'm going to be out of town. She was like, Oh, as if like, why wouldn't you cancel what you're doing to come to the Pornhub awards? The Pornhub awards. Who's hosted the Pornhub awards? I don't know who hosted.

I have no idea. It was Aza Akira who invited me, but, but I did not know who hosted. That was David idea. It was Aza Akira who invited me, but I did not know who hosted. That was my friend David Cho's old podcast partner. Oh, really? Yeah, yeah, yeah. She's a podcaster.

Was she on? Well, everyone's a podcaster at this point. Yes. You have a podcast. I have a podcast. I wanted you to have a podcast here. I know. I know.

It was hotly debated, but you were not very patient. No, that's not what happened. That's not what happened. We were like, we were doing a podcast. Great. And I'm like, I've got an agent getting offers from five different places. And then by that time, football season started.

Greg had a thing with his contract. He was trying to do with the NFL. The season already started. That was the thing. I was like, can we just wait till next year so we can do the whole season? Yeah. And by that time, by that time that happened, then I had a deal with Comedy Central

that was like for eight different things and the podcast. Yeah, yeah, yeah. But it was either here or there. And Greg had a thing where since he works for the NFL network,

Greg Rosenthal, there was a thing in his contract where he, a non-compete clause. Yeah. We were worried if we were at the ringer,

they might look at that more closely than they do at Comedy Central. So why'd you just blame me? You blamed me. This was, Because we could have split it through. We could have gotten through. You were just blame me? You blamed me. This was your side. Because we could have slid it through.

We could have gotten through. You were our first choice for a long time. I'm still here. The words, we don't know if we have room for it. That's not true. That didn't come from me. That's what I was told. And people lie to me all the time, so I would believe it.

We don't know if we have room for it. That's ridiculous. You already have an NFL podcast. And we also thought if we came here, we'd have to also thought if we came here we have like four basketball podcasts like our our podcast it's supposed to be about sports but we almost never talk about sports right maybe one off the field issue thing but then it's like some kid brought coke to kindergarten like we like stuff like that well that and this greg rosenthal was your buddy from way way with back when right yeah we met my freshman year

of college so 1997 what college Tulane yeah Tulane huh New Orleans for four years yeah

what was that like it was fucking amazing man I mean it was the best the best four years of my life hands down I mean cannot be recaptured cannot be repeated

I'll go back to New Orleans once a year just to eat but I mean the things you could do to your body 18 to 22 i mean just i can't even imagine full mardi gras every year with like off classes just not going to sleep for four days i mean it was it was amazing everybody i've ever met who went to tulane i'm always like oh my god whoa and everyone just laughs when before they answer how was tulane because it was indescribable.

That is New Orleans is my Achilles heel city. It's got every single vice that I care about. Really? Including like food that you can't resist but then you feel terrible

for like 18 hours. Yes. And you're combining that with the Harris Casino that's right downtown that I've had a lot of great nights in and all the other things New Orleans brings to the table. And I just can't handle it.

It bums me out that it's not a great comedy town. Like, I've gone back to Tulane to perform and they don't care. Like, I've gone back to New Orleans a couple times. They're like Miami and they're not a comedy city. You know, they have their music. They have their entertainment. They just want to talk to each other and drink. And I understand. It's like LA is to each other and drink. And I understand.

It's like LA is not a book tour city. No, no. Because there's too much to do here to be like, I'm going to go meet this person who wrote a book that I liked. But if you go to like Chicago, the best. People pour out. Yeah. What do you think?

What are the best comic cities? God, I mean. Like when you have like your schedule, what are the ones that you're like oh that place yes chicago is a great one chicago the people are the best yeah chicago is always amazing uh minneapolis is a great one atlanta is a great comedy town atlanta atlanta you'd be surprised nashville is a really good one and like in the south there's just certain markets i've never been to like they just have their own comedians that you've never heard of.

You're just like, okay. I think I said Minneapolis already. I love Pittsburgh. New York, of course, is great. There's very few bad comedy towns. When you're in Pittsburgh, is that like when CM Punk used to go back to Chicago? Same kind of reaction? They don't know I'm from Pittsburgh.

Really? Yeah, I have to go out and tell them. To wear like a Steelers jersey? I have to tell them when I graduated high school in which high school because they otherwise they're just like you don't sound like you're from pittsburgh you don't look like you're from pittsburgh i'm not billy gardell wearing like a jersey on my like the my album cover then i don't talk about pittsburgh things that they're always they're always surprised we're in like a better jersey yeah yeah younger i just had to get a new jersey i just had to uh i had like three

antonio brown jerseys i was like i just can't after i kept like holding on to antonio i was like you know what i'm still i still love the guy i still love him and then when he went after juju i was like man that was a weird move you already won what are you doing yeah yeah that felt like jealousy to me like somebody who leaves a tv show and then they replace him with the new lead of the show yeah like if caruso had gone after jimmy smith's and then ypd blue or something yeah he just there's some ego stuff going on there that had nothing to do i don't feel like with juju it was just like that's the next guy i gotta lob my grenade at him. Yeah.

It just made no sense. It just seemed like spoiled spilled milk. He was here. We didn't do a podcast, but he came in and hung out for an hour in Tony Brown before he got traded. And I got to say, he talked me into it in about 45 minutes. But I'm one of those people, if I'm in the room with somebody, they always win me over. Sure. But yeah, by the end of it, I was like, yeah, you do need a new team.

Yeah, screw those guys. I understood Le'Veon Bell, everything that he did. I wasn't happy about it, but I understood. Really? Yeah. It was like, you're not going to sacrifice your body for a year where they're just going to run you into the ground knowing you're gone next year anyway. True.

He's taking that money. Why not wait? It just feels like he lost money, though. I think he did too. But I understood his point of view on it. Antonio Brown was like, you want another team? Great.

But why are you throwing your trade value into the toilet every chance you get for this team that's done so much for you? I mean, they paid him a lot of money. He's gotten a lot of stats.

He's going to be in the Hall of Fame for what he did as a stealer. Not as for what he's going to do as a Raider. That I just thought, I wish he'd done it differently. What would be your opener for the Antonio Brown roast?

Fuck you. Fuck all your kids who look just like you. Something like that. Do you think he would be a bend over laughing guy or do you think he would be a Chevy Chase just silently smoldering the whole time sunglasses sunglasses on wide fake smile the entire time fake smile the entire time he'd only laugh he made fun of other people but there's that like there's that in between you just got a big smile on your face like when i remember when i did last comic standing

keenan avrey wayans hated me but he would just but he knew if the cameras cut to him looking mad he would look like a jerk. So he just had like a huge smile on his face all the time that I knew. Why did he hate you? Because I was not, no one expected me. They thought I was going to come out and host.

And I was like, no, no, no, no. I'm going to take this show over. Yeah. I'm going to make it my own and make fun of the judges, make fun of the contestants. I'm the best standup comic in three square miles from here.

And I'm going to let everyone know. Yeah. And they cut all of that'm going to let everyone know. Yeah. And they cut all of that out. They cut it off. Yeah. They told me, they're like, Anthony,

we cut everything that made you look like an asshole. And I was like, why do you think I did the show to look like an asshole on Last Comic Standing? That would have been so funny. I thought,

honestly, I walked out of Last Comic thinking I could get an Emmy for hosting a reality show. That's how crazy it was. And Jeff Probst was like, nope. Yeah, nope. I think Ellen won it for Game of Games or something.

No. Yeah. Wasn't even nominated. Let's take a quick break to talk about Vudu, a leading streaming app with a library of over 150,000 titles available to rent or buy from the latest blockbusters to your favorite indie films. They also have an ad-supported on-demand service

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if you like buying movies. Head to Vudu.com slash rewatchables to sign up and start watching today. Catch up on John Wick 2 before next week's Rewatchables episode at Voodoo.com slash Rewatchables. Back to Jessalyn. Who would be your dream athlete to roast right now? Who do you think would react the best? Who has the best material?

I mean, everyone always talks about Shaq, like you said. Shaq is, Comedy Central always thinks about getting him, bringing him on a roast or doing one of him.

How do you think LeBron would handle it? I think LeBron would be too controlling as to who he booked. Like, Comedy Central always thinks that if they class it up,

they're going to get George Clooney. They're going to get Brad Pitt. And it's like, like no if these guys wanted to do that they would do it themselves and control it all yeah like Dennis Leary's roast way back in the day one of the first on Comedy Central he had total control over what jokes were used and who was on the dais so I think that was there's like no Bill Hicks jokes that's what that those are the only things they cut but anytime someone mentioned Hicks, Leary had it gone. There was no reason to even do that. And athletes do not have a great sense of humor.

I mean, a person who would be fun to roast, like a Floyd Mayweather, would be fun to go after. I think he'd be good. Like Mike Tyson is the only person I've ever felt bad about roasting. I truly, I love the man and I felt bad making fun of him. And he was like laughing and he was pretty high, you know, a little drunk and like getting through it. But you just like,

I felt like this guy's struggling. I don't love, I don't love smacking him around right now. Cause I loved him growing up. Kobe would be kind of the most riveting roast. And I feel like it would end halfway through. Oh yeah. It would just be like over. Yeah, I can't even. And I think he'd be mad the whole time. I just think none of these guys have a good sense of humor about themselves. Like if you got like Jason Witten on the dais, you know what I mean? He would be furious within like five seconds. There's no way.

There'd be a lot of stuff about what was going on with his hair. Yeah. Or being the worst Monday Night Football announcer of all time. You think he was all time? I can't think of anyone worse. There have been some bad ones. There's so many bad announcers right now. We're in like,

this is a bad announcer heyday right now. I just can't believe it. I mean, God bless him. He's a legend, but Hubie Brown's doing the Celtics series this round. And it's like, I mean, he's like legend but hubie brown's doing the celtics series oh yeah this round and it's like i mean he's like 88 at this point it's just can i have somebody who's not just going to read the box score might point out some stuff with the game please with basketball i can't really tell

how bad an announcer is baseball it's very obvious which is why i think there are fewer in baseball fewer bad announcers in baseball but in in football, if you're bad, you've got like three minutes to show how bad you are in between every play that it really shines. Well, and also you have Romo, whose former teammate who is so much fun. Just killing it. Yeah, from the get-go, just that enthusiasm.

I think it's weird when the guys lose it. Like I always felt like Sims was pretty good. Not great, but he was good. He's passable. And then the last couple years, he was completely unlistenable. And I just want to know what happened. That's funny. I think I was just too young that he was grandfathered

in for me. I always remember him more as an announcer than as a quarterback. Really? Growing up. When he started to lose it, I didn't. It was like, oh, that's Phil Sims. I didn't realize that he was. But I guess you're right. I remember Madden and Summerall. Madden never really a hundred percent lost it,

but he definitely was better in the early years. Like I would say anybody. His Summerall though, it was tough to tell with Summerall that he lost it. Cause his style was, you know, very short sentences and stuff. But when he's just getting names wrong,

that's usually the sign with announcers. When they would show them in the booth toward the end, you were like, oh man, these guys aren't going to make it to the game. Can we get him in horseshoes? Yeah. Yeah, that was rough. So you think LeBron would control the whole thing, roast-wise? A hundred percent.

What about Tom Brady? I feel like he would be laughing the whole time and almost like not getting the jokes. I believe that 100%. Like I had friends who wrote for Peyton Manning on the ESPYs when he hosted. And then like a lot of times they had to explain the joke to him. And he would deliver it perfectly, but he wouldn't get what the joke was. And he's considered to be one of like the super funny athletes.

And I think he can be. I just think you have to tell him. I'm sure he probably just takes direction really well. You know, some people don't. I've talked about this on pods before, but the whole concept of athlete funny i really enjoy when an athlete is supposed is supposedly hilarious but it's only in the context of other athletes yeah yeah if you actually put him with a hilarious person he's not hilarious a total disaster i was like you know oj simpson you know of course from uh i've heard of him uh the double murder was hilarious and then you go back and try to watch, uh, naked gun now. And

you're like, that's not as good. You know, he peaked. He did. They should deep fake the OJ scenes and put like Barry Sanders in there or something. Try to save it. Cause that was like an iconic mid eighties movie. Oh yeah. And it's impossible to watch it now without the OJ part just overshadowing all of it. It's not impossible because he's not in it that much. And it's so funny. And he is like, he's like the roadrunner in that movie where he's always getting beaten up and tortured. You don't like, you're laughing at him,

you know, getting like dragged by a bus for like across the country. That it's not as hard to watch as I would have thought. It's funny watching these movies with my kids, the movies that I grew up on. And some of this stuff is so inappropriate. I mean, my kids, they don't roll with anything. But like the original Vacation,

first of all, they dragged the dog and there's just a leash left. And my daughter was so upset about that scene. She just wanted to stop the movie. I thought it was hilarious. But they put the grandmother in the car and they drive like a thousand miles with her. I don't know if they would do that now.

There's a lot of like, I'm not sure this would go now. Yeah, I didn't see the new vacation. I was wondering like, how do they change this to- They made it less funny. I got to imagine. I don't like when they redo the classics. No. If I can still watch the old movie, don't touch it.

Yeah. Especially a comedy. Especially a comedy. Comedy is special. There's no reason to remake The Bad News Bears. Have you had offers to be like the lead in a comedy or anything? Like I've had offers to be the lead in something that's like super low budget and it's never going to get made and never has been made.

But usually it's like someone offered me something and I'm like, I'm on tour right now. If I wasn't, I would, I would be happy to, like, I just met with like the head of an, uh, a, uh, a movie studio. And he's like, would you ever want to be in a movie? And I'm like, yeah. If the head of a movie studio calls me his favorite comedian and says, here's a movie role for you. I'm happy to do do it am i going to run through auditions right no i'm not but you know what i you know what i can do i've proven it give me the part and i'm there and i'll show up and and do do as well as i can i'm surprised you don't have like one rom-com in your background where you're like the lead guy's best friend who doesn't like the new girlfriend and it's just doing these pg13 insults. And then a year later,

you really regret being in the movie. Anytime they described it as like cute or I knew that they wanted someone just like a good looking young guy to be like the kind of the smart ass, I rejected it immediately. That was it? I wanted to play evil,

not like, not like, not kind of the smart aleck, you know? I wanted to be like a villain. You want to be like the Ooski, Dullrich and Scream, like that kind of guy. It turns out You know, I wanted to be like a villain. He would have been like the Ooski, Dullrich, and Scream. Like that kind of guy. It turns out

you're the killer at the end. You've taken everyone's virginity first. The example I always used was I wanted to be Craig Kilbourne in Old School. Old School.

Oh, yeah. Yeah. You know who else wants to be Craig Kilbourne in Old School? Craig Kilbourne. Yeah. That was a pretty big letdown

watching that like he that movie was so funny and he was just not funny in any of the scenes oh you didn't think so no i actually enjoyed how ridiculous the casting was that it made me enjoy his scenes i mean i don't think i enjoyed them for the reason he thought i was enjoying he was in it so little that it didn't like ruin the movie for me but i was like oh this is a missed opportunity like jeremy piven is that movie and it's funny that i'm like why is he i know why he's playing this character but they should have given him more to do uh but that movie holds up jeremy piven's been in a lot of stuff that he did you know he

was at major league we just did a rewatchables on major league and they cut him out of major league he was on the bench as an indian like bench jacky guy like who yelled insults out and they just cut his all the scenes out really yeah he's got like a really interesting imdb background that's funny this 80s 90s stuff i had no idea what about entourage you could have done yeah they never came to me for entourage but i would have definitely done that show. I saw every episode of that just like, hate watch, just like, I can't believe this is a real thing. Went and saw the movie Opening Day and like couldn't believe the people

unironically laughing. Like, it'd be like, come on, bro. And they'd be like, ha ha. I'm like, are you serious? This still gets you? I hope they make another one. If they made another movie. I mean, that movie did so badly. It did. That there's no way to make another one if they made another movie I mean that movie did so badly

it did they missed it's moment it's about two years too late I think so what happens now this Netflix special comes out I meant to ask you what was different about this special what was your mindset going into it it seemed like the pace of it

you slowed down even more than usual with your style like you were really trying to create like an atmosphere with it yeah part of that was i just wanted the jokes to like thoughts and prayers was like an angry special it's like i gotta get this off my chest whereas i wanted this just to be like almost like a rock show let's just have fun and every joke just be great and go into it that I really put a lot of thought into. And for the first time, I thought about how it would be as a special.

You know, I was thinking about that for years instead of just, all right, we're doing this now. What do we want to do? But I know I wanted to work with somebody big. Like I got A24 to produce it and they were great. I knew how I wanted it to open. And I always, I kept thinking about the first show. You know, every time, every comic who tapes a special tapes two shows back to back and the first one is usually bad yes almost

occasionally someone will tape just one and you can tell because they don't have things they can like move around to if something goes wrong they have to leave it in usually they tape two that night in a theater or wherever and the first one's bad because i'm off like i'm like in my first tapings i'm like i'll be a little sweaty you're just like you want to get it right and the first one's bad yeah because i'm off like i'm like in my first tapings i'm like i'll be a little sweaty you're just like you want to get it right and the audience is good but you're just not yourself and so this time i really was like that first one's gonna be great i'm gonna make sure it's great to the point that i went out and had mentally prepared myself enough that it was like that was like i thought that was the better show between the two tapings and to the

point where i almost didn't want to go out for a second show. I was like, maybe I'll just go out and screw around. Or maybe I'll just like, maybe I'll leave. Like, who cares? And then we did the second. And then they go, John Mulaney and Nick Kroll are here to watch the second show. And I was like, my friends are here. I got to go out and kill it.

You know, I can't let them see me do a bad show. So did that. And then afterwards, the director comes back. And he's like, that was great. We're definitely using the second show. And I was like, what do you mean? The first show was amazing. And he's like, we got better coverage in the second show. Just after watching you do it once, we were able to like, and I was like, oh, I'm glad I didn't just throw it out the window. But yeah, but that was one of the things I thought hard about. And it ended up, it still benefits

you because when you need to go back to the first show to cut something out, you look good. It looks the same. But that was, that's what I really prepared for on this one. One of the things I like when you do comedy is when you get mad at the audience and you take their reactions personally and you put them on the defensive, which is a really hard thing to pull off. Totally. I mean, usually I do it. That can go really wrong in the wrong hands. I've never had a good, it always gets a laugh from me if you keep it short and you go back to pull off. Totally. I mean, usually I do it. That can go really wrong in the wrong hands. I've never had it go. It always gets a laugh from me. If you keep it short and you go back to being

normal, like if you lose your temper, it's always going to be bad. Yeah. But I usually, I yell at crowds who are laughing, you know, for not laughing hard enough. And people love that. Yeah. It's rare that, and if I know a joke is just like, this joke should be getting a bigger laugh and it doesn't, like if a joke is too smart and that's the only reason. Like I went on like a European tour where I was like, are they going to understand what I'm saying? And they got jokes that American audiences didn't get. Really?

They just, yeah. They understand English better than they can speak it. And so they, but they got all the nuance that some American audiences just totally missed. I used to love Carson. It was my favorite Carson thing when he would take it personally when he didn't get a laugh on something. Oh, yeah.

And then Letterman learned to do his variation of that. And I remember the first couple years with Kimmel because he was really new as a host. And it took him probably, I don't know, two, three years to almost stop when a joke didn't work. Because initially, if you don't have the experience, the habit is just to rush to the next one because the silence made you uncomfortable or the lack of reaction. And it's so funny watching him now. He fucking loves it when the joke doesn't work.

Sometimes that's funnier than when the joke works. Oh, yeah. The facial expression when a joke bombs is better than anything else. Conan's great at it. Yeah. I think everybody, the reps of doing a show like that, eventually you're going to get good at knowing how to react. I think you just find a way to fill out the time.

Like, I'm sure, like, when I first start doing an hour, I'm doing 15 minutes. I'm thinking about that 15 minutes. Like, I don't want to go short. I don't want to go long. And then you eventually just feel at home in the space, and then you can let everything breathe. But Milton Berle had never told a good joke in his entire life.

His whole act was telling a joke that didn't work, and then he would react to it in a way that killed everybody. Uncle Milton. Yeah. Legendary SNL hosting performance by him. Yeah, didn't they? It's prominently featured in all of the books about SNL.

Didn't he just break out of every sketch and just refuse to do it? He's mugging and it was like everything they never wanted that show to be. Yeah.

Do you feel like, I've asked a couple people that come through about comedy classes where it's almost like sports where, you know, the guys in the late 80s, early 90s, they're kind of clustered and they all kind of came up doing the same clubs together

and they're all friends and then they kind of hit at different points around the same time. You kind of have your own class, it seems like. When you were coming up, when did you start doing comedy? Like 07, 088 so you're in there with aziz and aziz was in my class melanie kind of aziz melanie i've been i would say almost 17 years in

october i've been doing it uh aziz melanie um like bj novak was just like one like little class ahead of me yeah like i just remember like i would see bj novak on premium blend and i would say okay you know what next year i bet dan minak on premium blend and i would say okay you know what next year i bet dan mince gets premium blend and the year after that i'm gonna get premium blend and that's how it would work yeah like i just knew those guys and like their progression and like oh bj or dan mince got the half hour next year i'm gonna get the half hour and i would there were people that i could follow that aspirational jealousy of like oh this guy got it that means i'm going to get it next

but yeah my class i would say melanie um camille nagiani yeah uh tj miller pete holmes um yeah those are the guy or hannibal burris i would put in that class as well yeah but then we were came from all over i was one of the only guys in that class from la i met a lot of those guys when i moved to new york for a couple years they They were all Chicago people or New York people. Was Whitney Cummings in that class? Whitney Cummings, I think started right after me. She would be in that class too. Yeah. Yeah. She started in LA. Do you feel like there's a class now, like a late 2010s group that's emerging or is it just so different now with the internet? It feels like some people are making big leaps. Like I would put Ali Wong in my my class but for a long time ali wong was under the radar and now she's like one

of the biggest things in comedy yeah but she never went anywhere she didn't come from nowhere i've been watching her grow as long as i've been doing stand-up like sebastian maniscalco who's like a couple years older than me but uh and has always been working and now just suddenly blew up that you'd be like okay i guess we're in a similar class. But the people below me couldn't name one. Like that's how little I know now. If I need an opener, I've got to call people and be like, who's young and good?

Because I only watch people who I follow at the comedy store or at the comedy cellar. Otherwise, I'm not watching a lot of standup. What's the best place to do it in LA? Oh, the comedy. Actually know i'd say largo if you're lucky enough to be on that on that in that league because logo only takes a certain kind of comic yeah you got to be able to sell the place out you know 30 tickets it's a big place uh the store is more like you're going to see hundreds of people or like you know dozens of comics and so that's a little it takes the pressure off where i don't do as well uh on a comedy store show because people just aren't there they're

not all there to see me but at largo they're all there to see me and whoever i brought so they're they're good to them so i think i'd say largo is my favorite with the comedy store being a close close second you haven't played kimmel's place yet in vegas and it just opened up it just opened yeah everybody was going nuts about it They actually spent a lot of money trying to make like the best possible comedy place. For some reason it didn't really happen in Vegas. But it's a comedy club, right? Comedy club, yeah.

I think that's the tough thing is that there's so many theaters that do it. Like I always do the Mirage, like the Terry Fader Theater at the Mirage where Leno plays. You can just do one night and get the hell out. The idea of staying in Vegas for a weekend and having shows to do at night is like my biggest nightmare like my biggest nightmare do you gamble a little bit i'll throw money on the sports book and if i'm around for that like last time i played vegas under uh never never bet on or against the steelers okay never

because i don't want to like i don't want to double lose you know or like win the bet and lose the game. And then you're mixed up. I'll call my friend Greg Rosenthal and be like, what four games are pretty much locks to you? And do that. Then go the opposite way. No, he's good.

Is he? Yeah. I do bet on my own team. And it's been very profitable because I don't know if you're the Patriots have won six Super Bowls. So it's been really good. I didn't know that. Yeah, we're up to six now. I didn't know that. I didn't know that. We're up to six now.

I didn't know that. Yeah. I was in Boston. It's been great. Someone heckled me. They were like, fuck, what did they yell? Oh, a Steelers thing?

It was something about the Steelers. Probably a Roethlisberger related. And I was like, wait. They go, Steelers suck. And I go, really? I feel like it's been forever since we lost a Super Bowl. And it was right after you guys had lost the last Super Bowl.

And they were like, all right, pretty good. Pretty good. Pretty good. Yeah. I went to Steelers-Pats rivalry not to die. It was good there for a while. And then I felt like we really had the upper hand there for 10 to 20 years. We've never been underneath you ever.

20 years? I'm trying to remember. 96, I guess you had the upper hand. It was a long time ago. I mean, I'll never forget that AFC championship game. You guys just came out of nowhere and destroyed us. Oh, all the special teams touchdowns? Yeah.

Yeah. 2001, yeah. Cordell Stewart just falling apart. That's Cordell. It was the end of his career. Oh, that was it for him. That was it. 2001, yeah. Cordell Stewart just falling apart. That's Cordell. It was the end of his career. Oh, that was it for him. It was it. He was done.

It was unrecoverable. That game was a disaster. That's why every Pittsburgh Steelers fan calls the two Super Bowls that the Giants beat the Patriots the greatest

non-Steelers Super Bowls. It seems like a lot of people feel that way. I enjoy, like, listen, I understand why the Patriots keep winning. I don't, and I don't want to be like a hater and root against them. Yeah. But whenever like a lot of people feel that way. I enjoy, like, listen, I understand why the Patriots keep winning. And I don't want to be like a hater and root against them.

But whenever like a story comes out about like Brady and Kraft hating each other, or like Brady and Belichick hating each other, I love it. Like I love to hear that like they're all miserable, crying into their piles of money and Super Bowl trophies. Brady was at the Kentucky Derby last weekend with- Amendola? Yeah, like he still does it. 15 of his dudes.

I can't believe... And they go and they just do the whole thing. But wasn't it a fact that Amendola was on Molly last time he was there and he won and was giving away free money? And you see him, he's wearing mirrored sunglasses and looks out of his mind. I've heard variations of this story. I thought it was Welker, though. It was Welker.

You're right. You're right. But was he, I don't think it was confirmed that we knew what he was on, but he definitely just seemed super happy. Yeah, it was just, it was like you're too,

even though you won, you're too happy and you're wearing sunglasses inside, which is something that I'll make. Sunglasses inside is tough. Yeah. Yeah, there's usually something going on. And like,

if your sunglasses inside and you're chill, it's like maybe he's just sensitive to light maybe he doesn't want fans bothering him sunglasses and i'm handing out cash to whoever wants it you're probably on some drugs yeah do you want to make fun of jeff ross before we go i'd love to i'd love to i mean it's hard you know the guy's perfect in every way but uh i just think it's cool that he's finally moved on from the roasting thing it's you know he's finally moved on from the roasting thing. It's so funny. He's just like, I'm just going to get back into just pure stand-up

and just leave this roast thing behind. It's the funniest thing ever. We wrote for Jimmy for the AMAs one year in like the 06. And he was like, I got to get out of roasting.

I'm going to get pigeonholed. And everyone was kind of like, why? This is a great lane for you. Like, really? You think I should exploit it? And within five years, he was the roast master general.

But it was like, he was the last one to realize this is great real estate for you. He's also the only guy who could have stayed as long as he has stayed. You know, it was just, he hit the right tone

of like lovable, but silly. Like Lampanelli had like a short lifespan there yeah giraldo i don't know how much longer he could have kept doing it it was time i had three like he was like an edge too angry to kind of have a 10-year lifespan his last three or four roasts he almost had nothing to do with like it was like a lot of it was written for him he didn't care he would just go up and just knew how to deliver it yeah and knock it out of the park every time but

he didn't enjoy them like one of the reasons that i walked away after three was just knowing how miserable he was seeing how happy whitney was to walk away after three yeah that seemed like the right number to do yeah ross's he loves ross will be there for i don't think i think i think when jeff ross eventually passes and i hope that's 40 years 40 years 40 45 days from now uh um i think you i don't think you can ever do a roast again like i don't know how you do it without him it does feel like they might have to retire it yeah i the funny thing with him is i met him like in o2 got to know him pretty well through jimmy and those guys and you could clearly see the course of his life

where it's like he idolized rickles and those guys and you knew like see the course of his life where it's like he idolized Rickles and those guys and you knew like when that guy's 70 he's going to be whatever that generation's version of Rickles is still banging it out still a great late night show guest and all those beats and he's on his way he's the one comedian I know we're currently working today who could do a residency in Vegas until he's 95 and have it not be embarrassing yeah you's 95. And have it not be embarrassing. Yeah. You know what I mean? Have it not be like,

he wouldn't have to change his act. He wouldn't change anything. He could be truly be himself and enjoy it, I think. Whereas for me, and I know a lot of people, that would be Pure Ha. Well, he just loves making fun of people. But he's so good at it.

He walks into any room and he'll just see anybody and he'll be like, oh, look at this guy. And then he's, all of a sudden he's going the speed roast stuff he does live now

is amazing I've done like we did a college together and he's like come on stage with me and do the speed roast yeah and usually

I've seen him do it in an audience with you know a very diverse audience and you've got all these different people but in this college somewhere in New Jersey

it's like eight fucking white dudes who all look like Chad and then like one girl and Jeff's just going fucking white dudes who all look like Chad and then like one girl. And Jeff's just going down the line. And he could tell, like, if I'm like, I've got a joke, Jeff would throw to me, like, what do you got? But if I didn't, I'm like, I hope he doesn't call on me.

He wouldn't every time. And I was like, afterwards, I was like, how did you know not to, that I didn't have a joke? And he's like, I've been doing this so long, I can just glance up at you. And I know if you've got something or if I should just move on. Like, he can just move it so easily that it's a, it's like a, it's like a sixth sense.

I did the first, when I was writing for a Jimmy show, he guest hosted for a week and we did speed roast on Hollywood Boulevard. And that was the idea. And it was like, so Jeff's going to go out and he's just going to speed roast people as they walk by. And I'm thinking like, how the fuck is he going to do this? Like, so he's just going to see the people and have a roast. And I was the writer assigned to it. And we went, we had the camera crew and I'm like, this is going to be a fucking disaster. This is going to be the worst.

And then he did it for like an hour. Yeah. And he was just grabbing everybody. And then like, you know how weird Hollywood Boulevard is. It was like, he was like a kid in a candy store. Well, he's gotten good and like I could never do that.

If I started roasting people in Hollywood Boulevard, we'd get shot. But like, but Jeff, people like want to be roasted. It's like an honor and like they're delighted by it.

They're delighted to be made fun of by him that only he can really pull that off. I always like at the end of the roast when he's just crushed somebody for 12 minutes and he's like, with all that said, you're a great guy and you've been a great spirit and it's been an honor and I've been a huge fan. And he has a way of diffusing it

in 10 seconds before the hug that nobody else is as good at. But everyone says those same words. You're like, they like almost make you, but he's the only one who means it. Right. The only one. He genuinely does mean it.

I agree. What is the greatest roast joke that you've been the most jealous of that anyone ever told? Oh, for sure. Colin Quinn talking about Artie Lang, I think. Saying, Artie Lang did so much cocaine in the 90s. He once got a handwritten thank you note from Pablo Escobar. Just the idea of Pablo Escobar writing someone a handwritten thank you note for all the coke they did killed me so hard. It was like the best joke of the whole roast. I'll never forget that joke. You know, some of Norm's weekend update stuff is online now from the mid-90s when he's telling

jokes like that, but the audience isn't laughing and he's just staring in the camera. I would watch a documentary of those three weekend update years that Norm did where he just didn't care. Oh, yeah. You almost got that job, right? I mean, I auditioned for it. You were in the mix for it. And I thought I was like, the word was like, it's looking good.

You know, like it got to the point where they were like, Lorne Michaels asked for your phone number. Lorne Michaels doesn't call people with bad news. Yeah. Someone else, and then he, like a day went by and I was like, I'm not getting this. Is that a good thing or a bad thing? At the time it was a bad thing.

And now it's a good thing. Like I've talked about this before, but like that, it was so, that was a dream. That was the only job I ever really wanted. But to go in and kill the audition where like you're in the suit and tie at the actual desk, the camera comes down and they say, ladies and gentlemen, for weekend update, Anthony Jeselnik. And when I heard that, it's the announcer, I just started laughing.

Because I was so happy that my audition, I just breezed through it. I had my own jokes. I got them to laugh and they never laugh. And it was just Colin Yost having to tell the same jokes over and over again with just eight different people. And I was like, maybe I took it. And then I think it was just a thing of timing of like, Colin, let me do it for a couple of months. We're going to give him another chance at it. That I really haven't watched the show since, but I was just like, oh, it's so hard to get that close to a job like that, that I need, I need to just pour it all into the special.

Like this whole special was like me getting over that. Oh, really? So you were really traumatized by it. Oh, yeah. I mean, not traumatized, but it was a disappointment that I was just like, I'm not going to let, I didn't want the story of me to be like, oh, did you hear what almost happened for him? You know?

Like, you know the guy, you know, Doug Ray Scott? The actor. He was the bad, you would recognize him for sure. He's been in a bunch of movies. He was like the bad guy in Mission Impossible 2. I can't believe you just name dropped an actor

and I'm drawing a blank. This is like the lowest moment of my 2019. This might, you might realize, Doug Ray Scott was the bad guy in Mission Impossible 2. They had to do reshoots.

So we had to drop out of X-Men. He was going to play Wolverine. Gave it to Hugh Jackman. And Doug Ray Scott has never gotten over it. And I'm like-men he was going to play wolverine oh gave it to hugh jackman and doug ray scott has never gotten over it i'm like i'm not going to be that i'm not going to be bitter about and about like an audition that didn't go well no matter how badly i wanted it i'm just going to make the next thing i do even better and in the in the things that have happened to snl over those years i'm like i don't know if i could have i don't know if i could have been there through the Trump episode.

Not just because of like, Trump being on the air, but like, Trump telling me what jokes I'm going to tell. Like, no, that's never going to happen. I don't know what I would have done

or if I would have lasted or if the show, the show might be better now than it would have been if I had gotten that job. But it certainly would have gone in a different direction. I liked your Comedy Central show.

Thank you. Thank you. Yeah, it was fun, but it was, I don't have any regrets on that because it wasn't meant to live forever.

You know, it was so like pushing the envelope and the network at the same time. Like I'm working on a new Comedy Central show right now that's just designed

to be easy to do. Like I don't want to fight with a network. I just want to go shoot it. You guys have notes. You can do it in the edit and we're done, but it's not,

I think it'll be, I think it'll be as good, but it won't be, it. You guys have notes. You can do it in the edit and we're done. But it's not, I think it'll be, I think it'll be as good, but it won't be the same. Just, you know, fighting over joke after joke after joke. Yeah, yeah, yeah. Well, those days might be over and now you can just get right to people. I think that whole day of the network notes thing

is heading toward a slow ending. I mean, even when I did my podcast with Comedy Central, they were like, you're going to have standards and practices. And I was like, what do you mean it's a podcast? And I go, even when I did my podcast with Comedy Central, they were like, you're going to have standards and practices. And I was like, what do you mean it's a podcast? And they go,

we sell our ads throughout the network, so you still can't do it. And I was like, I'm not taking this deal if I have to do that. So in my contract, they're not allowed to give me notes on the podcast.

Really? Yeah. Because I was like, who would sign up for this if they didn't have to? And our podcast isn't so offensive that you're worried about what you're going to say. Right. But all those rules are weird. And yeah, you can circumvent

them easily now. What do the next couple of years look like for you? I mean, I'll do this show for a little bit. And I assume I'm going to want to jump back into stand-up. I think I have at least one more special left in me. But I just turned 40 a few months ago. And I'm looking at like, I used to think I would retire at 40 from standup, like still work and do things, but just be done with standup. But I think I got one more in me at least, if not two, maybe 50.

When you're out there, how many people are you playing to now? Anywhere from, I mean, if I'm doing a club, I sell out the club before I get to town. Yeah. No matter how big it is or how small it is. If I do a theater- But how many people is that?

I mean, it could be as many as like, you know, stand up live in Phoenix seats, 600. She saw five shows of that, you know,

3,000 people. But usually, it's about 1,500 to 2,000 people. And I'm thinking if on the next tour, I'd probably in the 3,000 range just from this special. You know,

it's like thoughts and prayers built up goodwill. And now it's a different time for Netflix comedies. I think more people watch them. Just wait till you get the Ringer podcast. That's, you know, get up to like 5,000. I'm going to use this as leverage. I'm going to be like, listen to me and Bill talk about how things could have been.

I'm here. My contract's up in 10 weeks. You can steal us. Is it really? I said, we have the- It's not even going to be a stealing. I'm just going to take it. We have the have the it's not even gonna be a stealing I'm just gonna take it we have the pickup

that's what I thought walking out of the SNL audition man you gotta I'll call you in one day yeah yeah call can you do it every week though

that's the thing that's the thing now that I want to pull back on we had we had a deal for 40 in a year yeah I was like I don't want

like if I have time off I don't want the only reason I'm stuck in la to be the podcast yeah but you don't have to do it in la they say you can do it on the phone but i i like doing because i'm with my best friend and we're messing around i don't want to do that over the phone that that's a that's a contractual obligation i don't want to have to do that so i think we might try to do uh try to do some fewer episodes so i'd like to i'd like to go live live in Berlin for a month you know like now that I have kind of money and success

and I can really go somewhere and write I stayed in LA and wrote for a year before I started taking this hour on the road at all I'd like to be able to go to another country

and write sounds great Berlin? yeah Berlin was fun man fucking Germans are there Berlin was fun I had a great time in Berlin you make great cars

it's true it's true. It's true. And they've lost some wars. All right, we'll talk. We'll negotiate. We'll figure it out. They've lost some wars.

Kyle, you've done a good job of not laughing too much during this. I've been keeping it under wraps. I've heard you go falling a lot. He was excited for this one. Good, good. All right, Anthony, a pleasure as always.

Always, man. All right, good to see you. All right, thanks for listening. Don't forget to go to DAZN.com if you want to sign up for DAZN. Don't forget about the Rewatchables 1999 Big Daddy. And don't forget about the Rewatchables John Wick 2 coming next week as well,

as well as Natty Hill and the Rewatchables 1999 feed. Don't forget about the Game of Thrones, our post-game show, Talk the Thrones, hashtag Talk to Thrones on Twitter as well as the Binge Mode Podcast all the Thrones content

we do put it up and Throne Game with me and Rassil Sunday night we're doing it again Kyle can't wait food, basketball

and then a little Thrones as well so we will see you late late on Sunday night until then Late, late on Sunday night. Until then.