Inside Late Night with Mark Malkoff - Jon Rineman Returns

Episode Date: November 12, 2024

Jon Rineman returns to discuss more of his time writing for Jimmy Fallon including Hillary Clinton declining a comedy bit, a real life Larry Sanders Show moment involving The Beach Boys, and working w...ith basketball great Larry Bird.     Buy Jon Rineman’s book: The Garden’s Always Greener Official Website: www.rinemania.com   Follow on IG: @rinemania Follow X/Twitter: @rinemania

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Starting point is 00:00:00 Hi, I am Mark Malkoff and welcome to Inside Late Night, presented by latenighter.com. Today, John Reinhman returns to the show. We discuss more of his time writing for Jimmy Fallon, including Hillary Clinton declining a comedy bit, a real-life Larry Sanders show moment involving the Beach Boys and working with basketball great Larry Bird. Now it's time to go inside late night. Jen Ryman, thanks for joining us. Thanks for having me, Mark. Happy to be back.
Starting point is 00:00:36 I read an interview with you, and you were saying that it was December of the year you were hired. It was Fallon's first year, a couple months in December of 2009, where you really found that the show found its voice, correct? Yeah, I think it was a Tiger Woods scandal. And I think the big reason for that is that, you know, when we were starting, the challenge was trying to find Jimmy's voice, trying to find what his stage presence was going to be and what his, you know, person's values were, you know, because there's some theatrics
Starting point is 00:01:08 to every comedian's persona, probably. It was finding out where the character, so to speak, of Jimmy Fallon would come down on certain things. And politics, he didn't really do political stuff. And he admittedly didn't know about it. So that was hard. Like it always felt like forcing that through anything with Obama or anybody else. And then he's not a sports guy. He is a music guy, but he doesn't want to make fun of anyone in music because they're, you know, he wants to be friends with them all. He wants them to all come on the show.
Starting point is 00:01:41 And then Tiger Woods was this guy who had just been on, I think, right before I got there. And everyone felt kind of duped. It was like he was, Tiger was this guy that would always have his wife and his kids run out on the course when he'd win and he'd hug him. And he'd always talked about his family and everything. And it's like, man, he's got 125 mistresses. And I think there was that.
Starting point is 00:02:03 I think it was Jeremy Bronson becoming the head monologue writer. That was a good combo for a long time. He and Jimmy, that worked. And it was the holidays, which is always one of my favorite times as a joke writer because there's so much new material. You know, you got to, you know, one of my jokes was, you know, well, everyone's talking about, you know, dasher and dancer and prancer and vixen you know tiger wood's latest call girls you know like stuff like
Starting point is 00:02:30 that and you can pull that out of the box in december just like you you can say what's the what's a christmas song i can make fun of just like i did and i think those three things it just was really freeing it was like okay we found what jimmy'll make fun of you know the kind of thing it's it's hypocrisy it's maybe someone that's it's not faithful to their family you you were telling me there was an Anthony Jesselnet joke that you really liked. What was it? Oh, it's one of my favorites. It was my favorite joke of his,
Starting point is 00:03:00 which was there's a new set of golf balls, and each one has a picture of a Tiger Woods mistress on it. And after inspecting the balls himself, Tiger said, I'd hit that. And that was, you know, perfect.
Starting point is 00:03:14 Like we were all just, you know, but then you take that and you can apply it to other stories. You get a little bit of confidence. And you say, well, hold on a second. And if I can write that, maybe I can write this political joke. Maybe I can write the sports joke.
Starting point is 00:03:27 Maybe I can write this music joke about things that I don't really know about or whatever. And our confidence grew by, I mean, that Christmas party in 2009, God, dude, it was great. It was, again, it was a dream year. It was like everyone was having so much fun. We were rolling. And it was just the dream team. It was me, like I, you know, as I said, the last time I was here, it was, it was me and the four in memoriams.
Starting point is 00:03:53 It was Jeremy Bronson, Morgan Murphy, Eric Legend, Anthony Jezzelnick. Somehow, some days, I'm getting the most on. It was just amazing, just an amazing time. And we all kind of found our roles. Like, Eric was really good at sort of the philosophical jokes. Like he would, you know, like, but it's going to stake when you blah, blah, blah, blah, blah, blah.
Starting point is 00:04:13 Like, it wasn't set up punchline with him. It was more like, and Morgan was really good at the act out jokes. Like she'd come up with a back and forth conversation sort of things. Jezelnick, as you know, he was the Hatchet Man. And then Jeremy and I were kind of pushing each other. We wrote very similar setup, run-up punchline, quick, quotable jokes. And so there was sort of that friendly rivalry. And so it was the dream team.
Starting point is 00:04:36 It was the best monologue team, I think, we had the whole time I was there. Because we all did something different, and we all pulled for each other. You know, we were all happy when someone got a lot on or when someone got a joke in New York Times or whatever. And I think Jezelnick had a lot to do with that. I said, he was, you didn't act out when Jezelnick was there because you didn't want to be on the receiving end of him calling you out for that, which all of us were at some point. And so you, you learn to behave, you know. Speaking of a dark humor, which Anthony Jesselneck is known for, a lot of comedy people, they have a, you know, a really nice persona. And I've met Jimmy Fallon
Starting point is 00:05:14 a bunch of times, really, really nice guy. But I've been told by a bunch of people that work there. I know you've said this as well, just much darker sense of humor when the camera's not on, sarcastic, but really, really funny. What I can speak to when I was there, yeah, his dark sense of humor, especially when he was in a good mood, like when he was in a really good mood and could just freewheel and be dark, man, he was as dark and as pitch black as anybody. And, you know, you hear those stories about Conan, too, like Brian Kylie always says that Conan behind the scene. I would put Jimmy against Conan. That's what I'm told. People would say that's insane because you hear Conan on this podcast now, you know, when he goes off the rails and talks about Santa screwing a birdhouse or whatever like he did when Gary was on,
Starting point is 00:06:01 just hilarious stuff. But Jimmy's mind was so quick and dark and he had such recall of random things from the past, like the, you know, the McDLT, you know, or baby Jessica or what I just weird random shit that he would bring out. And some of my best memories there were he and Miles in our monologue meetings just riffing off each other. And Miles was the perfect foil. You know, just going, oh, really? You know, the straight man. You know, really?
Starting point is 00:06:31 As I was in, Jimmy's like, oh, yeah, yeah, yeah. And then I ran into Cato Caelin. He was there. And, you know, he told us, oh, yeah, is that right? And just their riffing was the most funny thing. And then my role as I was the time he knew some of the operations. You know, I was the guy. I was the guy that would sit there as the prop
Starting point is 00:06:50 just waiting for Jimmy to make fun of my shirt or making make fun of my haircut or whatever but the flip side of that was I was able to give it back to him a little bit whereas other people didn't have that license and it was always a little bit scary and the room would kind of gasp a little bit but he'd laugh at it, he'd take it, we'd run with it and yeah his off-screen persona
Starting point is 00:07:10 when I knew him and he was in a good mood and he was being funny funniest human being of all the time. I mean, just like there's like you're just, you'd be crying. Like we've literally, you know, when people said to me like, did that show ever make you cry when you work there?
Starting point is 00:07:26 I was like, yeah, because I was laughing so hard, you know, during the meetings, you know, like is, you know, and well, at what? Well, I can't tell you that. You know, it's what happens in the green room
Starting point is 00:07:36 or what happens in the mono meeting. It stays there. And, you know, I can promise you, no one was hurt and all that. But it was just, you know, just a bunch of comedy writers.
Starting point is 00:07:44 let's talk about all the things we wish we could write about, but we know we can't sort of thing, you know. Speaking of that, you would sneak certain jokes in the monologue that you knew that Jimmy would never do, try to, you know, be a little bit more edgy. I know that you mentioned an interviewer. Somebody was interviewing you using an example that Louis C.K. said he would try to get stuff on with Conan a little bit more edgy. And sometimes Jimmy would do it at rehearsal just to amuse the writers or just to amuse knowing that it would never get in. Is that correct? Uh, yeah. Yeah, he would do, he would do it just get the monologue laugh. It was usually we'd put it at the end of the packet. So the monologue and he would say, that's just for you, take it home with you. You know, that's a, you're not going to hear that on the show tonight. Thanks for coming. Marshall Brickman, who was the head writer of Carson, tried to get Carson to do edgy or stuff as well. I feel like that that's probably happens with a lot with some of the hosts. Well, I want to, hey man, I, you know, not to put myself over too much using another wrestling term. But, you know, when I was. running mono the last year and a half or so that i was there miles was gone or he was there but no longer really the head writer and uh was more working in a producing capacity you know i want to take some credit i got him to do some pretty dark stuff we did a lot on the me too
Starting point is 00:09:01 movement uh we did a lot on harvey winstein uh roy more that guy the creepy guy that ran down there in the south uh we we hit him really hard uh i got jimmy to do two jokes about charles man Johnson dying. And I take that as one of my greatest personal achievement. I wrote one of them. Like that, you know, I, but we were able to put two together that made sense that felt like Jimmy. And you could see in his eyes, there was a little bit of excitement when he went into the setup. Because it was like, we don't really do a whole lot of this, but they both worked. You did an interview. You were talking about that you were in the Q card room one time or the control room. And you were surprised about how much things.
Starting point is 00:09:44 were scripted that you didn't think would be scripted. And you said some of those spontaneous moments. You wondered in late night, some of those classic moments that seemed very spontaneous how scripted they were. What are some examples of some things at Fallon that maybe the audience would be like, oh, wow, that's really that that happened. I can't believe that happened. That was maybe planned.
Starting point is 00:10:06 I still to this day, think he knew the Nicole Kidman thing was coming because their mutual friend who I happened to know. I don't know whatever happened to this guy, but he was a producer at the time. So maybe he's doing great. And if he is, I apologize, Rick. I just genuinely don't know. I've lost such a lot of people. But there was a producer that Jimmy and Nicole each knew and had worked with. And he was walking around backstage. So it was a little bit like a wrestling thing. It's like the Montreal screw job a little bit. I'm a skeptic of that to some degree. And I love Brett Hart. Part of me still wonders. Folks, if you go on Wikipedia, Google Montreal screw job. It won't get you fired. It's a wrestling scandal. I just want to interject. I was literally talking about this with somebody last week that I have so many still questions. Yeah. I know it's amazing that people still talk about it all those years.
Starting point is 00:10:58 As maybe we'll get to. I went through a somewhere thing myself, but, and that was not fake. So I have to respect Brett saying it's real. But with Nicole Kidman, I still think, without getting too deep in it, because a lot of it is, you know, a lot of it's just friendly talk, not locker room talk, like none of that, but a lot of us just friendly talk about who we were in college and who we were in high school. And I don't, Jimmy doesn't strike me as that, he's a very perceptive guy. I just can't believe that Nicole Kidman would show up at his apartment and he wouldn't jump
Starting point is 00:11:35 through the roof. Like, oh my God, Nicole Kidman's here. How can I impress her? So there's that. He said a couple things that are inconsistent, just telling stories to me about, just innocent story. Nothing scandals, just about just girlfriends he had back in college or his prom date or whatever. I'm like Jimmy, Jimmy knows is like he knows people. And so that conflicts with the person we hear about and then the Cole Kim. So that's a clash. And then their mutual contact, Rick was there that day walking around. And I just, from being in the green room in later years, or the cue card room, I should say, and hearing how things would be planned and how they would come out. And sometimes it'd be my idea. I'd say, why don't we do it this way and make it
Starting point is 00:12:17 look, you know, would this look more real or whatever? I just feel like 80% feel like that was a work. Like he knew, I think that I think he probably found out, he might have found out that day. Like Rick might have gone in and said, hey man, Nicole's here. She's going to tell this story. And Jimmy might have said, are you serious? I always wondered about that. And then, but when they got out on stage with that thing of like in the moment on TV, Jimmy realized he did. No, man. Like I think backstage there was some smartening up that went on there that's just that's just me that's my opinion i would imagine with a taylor swift she's she's on the show and then they have this embarrassing video of is it her her mom took or something and she's reacting oh she knew yes that's what
Starting point is 00:12:59 i'm saying that stuff they always know they always know yeah there's never any i mean especially with jimmy uh i mean even wakene phoenix on david lighterman dave knew he blew the gimmick at the end he stood up and took the glasses off and shook his hand david admitted he knew. I slapped my bed when I was watching that lie. I said, you just blew it, you fool. Like, you just had the most famous segment ever. And now it's only going to be like an A-minus because you took off the glasses and shook us. Like, you blew the gimmick. Rosie O'Donnell on her show, which was, it was such a huge show at the time, the syndicated show. She had this bit where she would be blindfolded and there would be his famous person come out. And it would kind of make noises.
Starting point is 00:13:38 And she would have to guess who the person was. Oh, yeah, I saw the Richard Simmons one. And she revealed that she knew. I mean, that she's like, I knew. This was like in the last couple of years, she's like, I just, I know that I just, I did know I could make it funnier that way if I knew in advance. Let me tell you something. I'll tell you a couple of moments. Like the Bradley Cooper laughing with the elephant man, that was, that was 100% genuine.
Starting point is 00:14:00 Like, they were really trying to. That was great. They just happened to have those dumb hat. And that's why it's so great. And you feel that as a comedy writer. Like, you're like, that's real. Like, and I saw it happen live. he really they they screwed up like they i think they in the planning of that segment took something
Starting point is 00:14:17 out of the middle or whatever or maybe kill or maybe they were supposed to be a commercial or something but we had so much show they gave him one big segment and so there's no chance to take off those crazy visors with the funny hair and bradley really was trying his damn to sell that i mean we know from the movies he's done since he's a serious you know he wants to win the award he wants to be the serious actor that play that affects your life and he really was trying to sell the hell out of that movie and they really that was 100% genuine um to my knowledge when stevie wonder popped out of the cake or whatever to saying happy birthday to jimmy when he turned 40 i don't think jimmy knew about that i think he knew there was a special guest but i don't
Starting point is 00:14:56 think he knew it was going to be stevie wonder which was fantastic but uh and then the hair tussle with trump that was planned like that was a that was a thing going in that it was part of a much bigger stunt uh callback wise that they were going to do with hillary clinton And Hillary said, I don't want to play ball anymore. So we got caught. What was the bit that Hillary that was pitched to her? She had been coughing a lot. And she'd had pneumonia, I think.
Starting point is 00:15:22 And there was a rumor that she might be gravely ill, which was not accurate, obviously. And so to prove that she was not sick, the bit that was pitched and supposedly approved, although it didn't happen, because I was skeptical. I was like, I don't know about this, was that she was going to grab Jimmy by the tie and give him a big kiss on the lips and then kind of push push his face away so she was going to put on the lipstick and you know make sure it's stuck on his face and everything so if you're going to kiss Hillary Clinton which would have been I would have loved it just because I hate Bill you know I'm a I'm a liberal leaning person but I hate Bill Clinton which you'll probably
Starting point is 00:16:01 figure out a surmise by reading Garden's always greener he's a routinely made fun of in there this book I wrote but I thought it was have been great for Hillary. It would have been a great moment that she gets to kiss Jimmy Fallon on the show and everything like that. And I guess to balance that out, because they didn't want to show bias, they were going to, they did the hair tussle. And, you know, I was like, why don't I mess up his hair? And here's my thing about that. I had, I had nothing to do with the hair tussle. I really didn't. I didn't know it was going to happen. I don't think any of us really knew. We knew about the Hillary bit because we had been told no Bill Clinton jokes, you know, for a week or two or whatever.
Starting point is 00:16:40 be very careful. Be careful with the jokes. You make no sex jokes, whatever. We want to make sure she'd feel comfortable doing this bit. And I think we didn't even do any jokes like that in the motto at all. I think it was like, keep it clean, you know, because this is a big thing for us. And the tussle would not have been as big a deal if he'd done an interview. If he'd done a real interview with Trump, with some real questions of substance, that hair tussle, instead he said things like, we're getting close to the election, how are you feeling? And this is starting to get real. up just being a softball interview ending with what was supposed to be a blow off. As you say in wrestling, the blow off from a tense interview was going to be, hey, we've been going at each other.
Starting point is 00:17:20 It's been awkward here for eight minutes. Can I just fuck up your hair and we'll make up? In defense of Fallon, I personally find it completely ridiculous that people think that that was something for him to get all the brunt when he went on Saturday night live and he was doing all these other things. I just don't. And also Colbert admitted people never. to talk about when he went on Trump went on Colbert. And Stephen even says, he said later, he's like, I wish I was tough on him. I think he has one thing that was a little, that was tough. But I'll tell you a story from that day that is the difference between who I was at that
Starting point is 00:17:56 point in my maturity and who someone else is in their maturity and why they're still working and happily employed and I'm someone that comes with a warning label because of past misdeeds is that Chris Belair, who I know you're friendly with. And Chris Belair, from listening to your Carson podcast, I heard the story when I believe Bill Schiff was on. And he told that famous story about there was a night when David Letterman really wanted to listen to the Eagles. And so he's like, can't we play some Eagles? And Paul's saying, no, no, no, anything we play is going to cost us.
Starting point is 00:18:33 And Rob's yelling at him, no, you can't do it. and Barbara Gaines is saying, no, no Eagles, you can't do it. So Chris Baller's day is done at that point. He's done his writing. It's the middle of the show. Dave's just screwing around. And Chris Baller goes and looks up on their MIDI music file, like all the archive music and the royalty-free music,
Starting point is 00:18:58 and just look, spends the whole show out of his own free will, looking up songs that maybe would sound like the Eagles. until he finds one that sounds like life in the fast lane and sends it down in the studio, sends it down to Bill, they play it, and they play it on the show, and it's what classic bit from Letterman. And it's because Chris went the extra mile. Chris is a good person. Agreed.
Starting point is 00:19:22 Chris will be a team player. And he worked out of his position that day and created a classic moment because he was helping out. Now, me, that day that Trump was on the show, I'm in a bad mood because, Miles left me a whole bunch of stuff to read that he didn't get to. So now I'm feeling like, uh, on top of all the stuff I've got to read. Now I got to read everything that he didn't get to from thank you notes or whatever, some bit or something or something for the mom.
Starting point is 00:19:50 Maybe it was like a joke bit for the motto, but I got to read through everyone's jokes for this. And an email went out to me and three other writers that said, we need more Trump questions and said, we want them from you guys because you're the dark, darkest joke writers. have, you know, you think it, make it funny, make it interesting, whatever. And I started to do it, and then I said to myself, you know, I'm already doing some of Miles's job today. And I've been here for, I think of that point, seven years. So I'm a little bit jaded. And I'm tired of doing other people's jobs. I'm tired of helping out when there's a sketch that's short. I'm just not going to do it.
Starting point is 00:20:29 And so when I woke up that next, I think about that every time when I see that hair tussle and what it did to our show. And I look at none of us helped out. All four of us said had the same bad attitude that I'm busy with something else. I'm not going to do it. But all I had to do was submit maybe two or three questions. If one of them gets on there, maybe that interview goes different. And I always tell that story. Like when I taught at Emerson, I tell people that story. I say, I was selfish. I was immature. I said, I don't feel like being a team player today. I'm not playing out a position. I'm not doing it. Whereas someone like Chris Belair will go that extra mile. So, you know, yeah, it's when people say, well, the hair tussle wouldn't have been
Starting point is 00:21:15 as big a deal if Jimmy had asked some questions. I always say to them, hey, I was asked to submit some questions that day. And I just said, I don't feel like it. And I knew I wasn't going to get in trouble because at the time I was, you know, untouchable or whatever. The next morning, watched the interview in horror, because, you know, I'd gone to bed and everything the night before. I was a rare night where I'd gone to bed early, but people were waking me up and saying, what the fuck, man, what is your boss? What's going on here? And I saw the image. I was like, I don't get it. And then I watched the interview. And it was a life lesson, learned too late that was like, man, do what to ask of you, be a team player. If you can, if you can contribute something in a
Starting point is 00:21:59 different way, you really should. And it could make the difference. In Chris's case, it created a classic comedy moment from an iconic show. And maybe if me and one other person and written some hard-hitting questions that day, maybe the hair tussle never even happens. Maybe Trump is in such a bad mood. He says, fuck you. And Jimmy looks even nicer at the end. And, but yeah, it's bullshit. It's people that say Jimmy is at fault for Trump being elected. And that's bullshit. Trump, that hair tussle had nothing to do with any of that stuff. Tell Hillary to go visit the swing states.
Starting point is 00:22:35 Tell her to go to Wisconsin every now and then. That's a bigger deal than what Jimmy Fallon's doing. Come on. Can you share any Larry Sanders-esque moments backstage with guests or just behind the scenes? Sure. Or like this would be maybe get on Sanders. My favorite day I ever working there. Well, there's two favorite days.
Starting point is 00:22:55 It was Halloween, 2017, is when my daughter and my wife came in. It was the day that everyone got to meet Sadie for the first time. It was Halloween, so she's dressed up. And Patrick Borrelli had a daughter, too. And so it was like this great moment for us. Two guys from Boston was like, you believe we had a kid? Like, you know, like, we never thought we'd have families and kids and stuff. And here we are.
Starting point is 00:23:16 And, you know, Jimmy got to meet. and I got a picture of the two of them and all that stuff. That's my favorite, favorite day. My second favorite day is from late night, and that was when the Beach Boys were on. And I don't mean like the Mike Love Beach. I mean the Beach Boys, Beach Boys. Brian Wilson.
Starting point is 00:23:32 Brian Wilson and David Marks and Bruce Johnson and Alan Jardine. My favorite backstage story is I'm just a diehard fan. And I'd already spent the whole day hanging out with everyone but Brian. Brian was on his own and was 100% with it at the time, by the way, too. He was leading that band, but he was off on his own, doing his own work and stuff. So I hung out with the other four guys, Beach Boys, all just five of us, just hanging out, telling stories. But then I kind of started to overstay my welcome a little like I'd been there. Now it's the show has already happened and I'm still there when they
Starting point is 00:24:06 come backstage. Hey, guys, I was there. Okay, great. And I go up to Al Jardine and I start talking to Al Jardine, and I'm talking to him, and I'm talking to him, and I'm talking to him, and he says something like, yeah, well, crazy days or whatever. And then his wife comes and grabs and goes, oh, Al, Jimmy wants to talk to you and pulls Al away. Oh, I'm so sorry, John. This was great, but we'll catch you up next time, pulls him away. So they go over to Jimmy, and Jimmy's like, Al, Al Jardine. Oh, my God. And they're talking. And I watch them talk. And then I see Jimmy, the light in Jimmy's eyes start to go out a little bit. The more Al talks to him until finally Jimmy goes, what is going on? Which is the cue for Kelly, his assistant to come grab Jimmy and pull it. And Jimmy, the car is waiting for you. You got to get downstairs. And Jimmy goes, oh, Al, I'm so sorry. We'll catch up next time. Does the same thing. Okay. So now Jimmy's pulled away. And as he's being pulled away, Brian Wilson walks around the corner. And Jimmy goes, oh, my God. And he goes, I didn't get to talk to.
Starting point is 00:25:14 He puts his briefcase down and everything goes over. He goes, Brian, that was unbelievable. And he shakes his hand with both hands. And he's like, oh, my God, you guys were great. Oh, my gosh. Can you come on, do their hearts for full of spring? Can you come on for Christmas and do little St. Nick? Oh, my gosh, dude, it would be great.
Starting point is 00:25:30 And he's doing, oh, yeah, right, right. And then all of a sudden, Brian goes, yeah, oh, he starts feeling faint, start to act like he goes, oh, where, where are, my what's happening and then everyone like brian's wife his manager jeff foskett they all run over there brian oh my god are you okay and then jimmy goes oh my god i'm so sorry brian thank you and leaves brian gets around the corner stands up straight goes like this and just keeps on while and so it was just walking watching that food chain of i don't want to talk to anybody like it was just that thing of like like the beach boy doesn't want to talk to the writer the host doesn't
Starting point is 00:26:09 want to talk to the beach boy the leader of the beach boy is doesn't want to talk to anybody and it was just that thing of like and rebecca and i still talk about it just like you know like whenever i'm having an important lunch whatever she's like just remember the you know remember the al geridine moment remember when it's time to to bail and i'm like yeah yeah yeah but it was like seeing that happen and then feeling not as bad like i was like oh jimmy just got blown up you know like it happens so yeah we there's stuff there's other stuff i can't talk about but uh out of respect for people, but that was one that stuck with me as a very Larry Sandersie's moment where it was like, no, it's a talk show, but no one really wants to talk to each other,
Starting point is 00:26:47 you know? You actually lived one of the Larry Sanders stories on the show, which was that they had filled the writer who would only be really good at his job, or he was, let me say he was the best at his job when he was miserable. Yeah. And he was really just in a down place. And he was on the, on Sanders, he was dating somebody who was all half. happy and the quality went down. So they purposely, I think, offered the woman that she was dating
Starting point is 00:27:15 something. I forget what it was to break up with Phil and then he's miserable and then the quality goes back up. But you've said in at least one interview that that was applicable to how you were as a writer. Yeah. And it's it's advice I've given to other people, which is you can't write from an angry place. It's really, that's what I did, and I did it for, you know, eight and the nine years, probably. I think I, after the first year there, I got really bored. I mean, there were days where there was a day I got like nine jokes on the show. And then I think I got 10. And it was just like, you get to that point, you're like, what else is there? Well, the answer is, you talk to your agent or manager and you figure out what else is there. And maybe you go do
Starting point is 00:28:05 other things. That's the answer. Someone like Rebecca Shaw or, forgive me, I can't think, I apologize, I can't think of her writing and life partner's name, but the two of them were both at the show after me and did a bunch of memorable bits and then moved. You know, they got off the show after about a year and now they have a new comedy coming out on FX. Yeah, that's what you do. You know, it's like you, you know, and Anthony said that to me and like, you know, he was always urging me to go But instead I stayed. I needed the money and I wanted the money and I loved 30 Rock and I loved being in New York and I loved Rebecca and I didn't want to make her move California and I didn't think she would. So I thought that that would end that. And so after the first year, I just got really bored and started acting out. It goes back to when I was in school. That's kind of how I was in school. I would go up and down. I would get really good grades and everyone would be happy with me and I'd get bored with it. So then I I would say something smart alicky in class, or I'd pick on something or whatever. It got to the point where the only way for me to motivate myself was to kind of get mad,
Starting point is 00:29:17 was to find a way to like, let it be like, you know, I've always gotten a joke on every Friday. So I have to get jokes on today or else I'm going to lose my streak of Fridays. And I got to really make sure no one can bother me while I'm doing it. Or, man, it's Friday. And I've only gotten 12 jokes on this week. That means I got to get at least, you know, three more. I've only gotten 11. I've got to get four more than the normal three or whatever. And, you know, when you're working with people like Jen Statsky or Morgan Murphy or Eric Legend,
Starting point is 00:29:49 people who've gone on to great, great success in this business, but are famously mellow, easygoing human beings as opposed to robotic sort of almost militant writers. That doesn't rub off so well on them and when it's time for them to go you're kind of the first one that they parry that they're like man i'm glad i don't have to work with that guy anymore so you're right and that every day or night depending on you know how i was doing it that i was in just a really good mood the jokes would be soft and every day that i came in ready to fight and ready to guns blazing and the The shirt was, you know, rumpled just because my shoulders were up and everything. I killed it and I got really good jokes on.
Starting point is 00:30:37 And I think that I mentioned that day of October of 2017 as being a favorite day. And it wasn't just a favorite day because of the circumstances. That was one of the rare days where I just had fun. And it was, you know, I just had fun with everything and it was Halloween. And I just said, I told myself, I said, look, my wife and my baby are coming in. I'm not going to be an hour. today. I'm just going to break character. And, dude, our monologue
Starting point is 00:31:04 was off the hook that day. We were so good. Everyone got something on more. Everyone got multiple jokes. I think we did about 20 something. I got six and they were all fun laid back, but I didn't learn anything from that. Like, I didn't like, it was just like as soon as
Starting point is 00:31:20 the next day came, you know, I was never someone who would go around picking on other writers. I was not, despite the bullshit And the rumors and the stories that have flown around, I was not someone that yelled at writers working under me. That is not true. In the year and a half that I was there with filling in for miles, I made it, that was my only goal was let's get through this without yelling at anybody.
Starting point is 00:31:47 So I didn't yell at anybody. Did I have to say to somebody, you know, I won't name them because they're still there and I don't want to create drama. But like, there was someone there that, you know, I had said, no more Trump jokes. Jimmy said, we're all. that you got eight that's it we're doing them and the very next batch jokes i got were three trump jokes did i call that person up and say hey what the heck is this yes i did i didn't yell at them but the thing is when you to write your own stuff give off this aura of being unpleasant of being unhappy people stay away they don't know what your deal is and they think they might take it personally and they might think oh he's mad at me and he's giving me some mad it's like being a
Starting point is 00:32:29 porcupine. And so, yeah, it was, I wrote from a place of anger for many of those years and have since learned how not to do that. And it's, you just have to, I didn't even realize it, but it was just, Rebecca said at one point, there was just one point where we were all having dinner, the three of us, being Sadie and Rebecca, and she just said, you know, I'm so happy that you've gotten to the place that you are. And I was like, what do you mean? She's like, and I go, am I that different? And she's like, yes. And she went back. and named all these times when we were together where I was just making up things to be mad at. But you just can't do it.
Starting point is 00:33:05 You're just going to drive yourself into the ground. And, you know, like when Statsky won her Emmy or latest Emmy, I sent her an email to congratulate her. And I didn't hear it back for a couple days. And I started to get that pit in my stomach where I was like, shh, like, is this another person? And when she wrote back a really nice email, it just felt so good that it was like maybe the word's getting around that it's like you can talk to Ryman like it's it's okay and you know but it's um if I'm a cautionary tale hey man I had it good for a long time you know uh hopefully other people can learn from it and have a really good career this happens on other late night shows I mean
Starting point is 00:33:46 it's something that you um you I mean your story of just how hard it wasn't all the obstacles and we'll get to everything um a little later but you were known in at the beginning you You said, quote, is a rookie with a temperament. Yeah. And you said that Miles and Jeremy had to sit you down and said, you have to stop acting this way. What was your response to them? Did you see that?
Starting point is 00:34:09 The way they framed it was, and they were right, is that, you know, when things ultimately broke for me, it was January 8th, 2018. So 1-8-18. And I had a TIA mini-stroke. On the subway. On the subway, on the path train, yeah. And I know, it was on the, you're right, it was on the subway. And somehow I got on the path. I don't remember how I got to Hoboken home, but I did. And what they warned me about, this is 2009. So this is almost eight years. This is like just over eight years beforehand. The way they framed it was not, I wish they had framed it as you have to stop doing this or else we're going to fire you. I wish they had said that to me. That would have woken me up real good. Because my dad was still around at that point. and the thought of having to face him after fucking up at this great dream job,
Starting point is 00:35:03 that would have, and other people that were mentors in my life who were around at that time, I would have woken me up real good. And it would have, you know, and I'm sure Miles would say, yeah, I fucking wish I did that too, you know,
Starting point is 00:35:17 like it would have made his life a lot easier for at least a couple weeks. I wish they had said you had to stop doing it. The way they framed it was you're going to burn yourself out. you're going to hurt yourself if you keep taking it this seriously and if you keep acting like this and the irony of it was i was angry because of the way of it wasn't my joke didn't get on it was an element joke meaning there was a sound effect and i wasn't happy with the way it was executed it still got in the show i got credit for it jimmy liked it lorn thought it was cute. The audience laughed, but because it was only 80% executed the way I wanted it to. I was
Starting point is 00:35:56 furious. Like, I was fuming. And I sent them both an email and said, I wish you would just cut this joke. And they sat me down and Jeremy did that many, many times. And then after Jeremy was gone, Miles said many times, like, you really, like, you would say, I know coming for me, this may not be what you want to hear, but maybe you look into therapy. Like, this could, you know, really help you. But again, it's like you talked about the guy from Larry Sanders, where it was just like all that mattered to me was how well I did at that job and how many jokes I got on that show and that they got funnier and funnier and then I got more and more. And then I, you know, fed that beast. And there was this personal, you know, because I used to be a distance runner, I think it was
Starting point is 00:36:42 that mentality of don't stop, don't slow down. As soon as you slow down, as soon as you slow down, things are going to hurt. You're not going to be as good. You're going to tighten up. And I just didn't listen. I would listen for a while and then something would happen in and I would act out. But you can't, how do you punish when you're a show that is new and trying to stay on the air because Dick Ebersaw is, you know, from reading Bill's book. That would be Bill Carter. Bill Carter, yeah. I, you know from reading his book that Dick Ebersall was poking around trying to get us kicked off the air. He was trying to have it be Jay and Conan again. And so when you're the number one writer, even as a rookie on a show that is on the chopping block because they're trying to cut a late night show, they're not going to punish you.
Starting point is 00:37:26 They're just going to give you talks. They're going to talk to you. They're going to tell other people like Morgan, like Ali Waller, like Eric Legend, they're going to tell those people, hey, just deal with them. He's fucking crazy. When you leave this show, you never have to deal with him again. But just we have to put up with him because he's good and we're trying to keep going here. and then there was always something like that. Then it was we were trying to get the Tonight Show.
Starting point is 00:37:49 And so when you're trying to get the Tonight Show and I'm being an asshole again and I'm treating Jeremy like garbage, what are you going to do? You just tell everybody, just deal with it. You know, something I've done in between, like when I was, like I said, I'm going back to school and I'm completing my master's degree. And something I've done just to have something to do on some days. Like, you know, you don't do it to get rich, but I've been a substitute teacher. And I've gone back to the school, I went in my elementary school, actually, and I've been teaching sixth grade, and, you know, you learn your attitude with certain kids who act out is, well, they're not following the rules. They're not doing what I told them, but they're not bothering anybody right now. It's like if I go poke the bear, they're going to bother the rest of the class. If I let them just keep break the rules and watch YouTube on their computer and they're not bothering anybody, take the win. You know what I mean? And I think that was,
Starting point is 00:38:43 what Miles' attitude was with me, which was, as long as he can put out the fires with everyone else that I annoy, just let him get away with it. You know, that's just the business side. And, you know, you always think that like, you're invincible. You know, every time you get away, every time you get away with another transgression or, and again, I was, it was never anything like scandalous that you get fired over. Like, it's never anything you read about. I, I was not someone that went around picking fights and making fun of people. I was not someone that I always root for the underdog. So I was never going around making fun of people's clothes or making fun of new staffers.
Starting point is 00:39:20 I was always nice to the interns. Obviously, didn't sexually harass anybody. That's, I don't even know how to. You know, that's, I mean, you can see. I mean, this is, I'm dressed like Forrest Gump for sake. You know, but I was just unpleasant. And you always think with each turn that I'm invincible and I'm always going to get away with it. man, there's always someone for each of us.
Starting point is 00:39:44 There's always going to be someone that comes into that job and comes around the corner and they're going to be carrying a big, big club that you didn't expect. And they're going to have your number. We're going to get to that in a little bit. But, I mean, your whole journey, I appreciate you being just so honest. I mean, the thing is, I've worked on late night. I had friends at late night. And I've had people that have told me that have been let go from jobs.
Starting point is 00:40:08 they're like, I didn't do anything. I have no idea why this happened. And they tell their friends that. And their friends are like, I can't believe they didn't. I'm so sorry. And then I'll talk to like other people that worked at this show and they'll tell me actually what happened. You're taking responsibility.
Starting point is 00:40:25 A lot of these people, I don't know, I didn't even do anything. They'll tell me they did this, this, this and this. Well, it took me a long time, Mark, to get to that point. And it took me a long time to be mature. And I know we're both wrestling fans and someone. I got to work with for a little while, and I, I mean, I'm listening to his podcast really changed my life, a guy by the name of Bruce Pritchard. Absolutely.
Starting point is 00:40:46 I know who he, I used to watch him at Hershey Park Arena when he was Brother Love. Brother Love. And now he's a very divisive figure, you know, we never know day to day what's going to happen with WWE right now. They just had another big couple bombshell articles come out, a new lawsuit and all that. So I don't know. Like, you know, for all I know, I know he's close with Vince, anyone that's close to Vince, you know, you got a target on you.
Starting point is 00:41:08 So, but I can only speak to my experience with Bruce Pritchard, which was very, very positive and very giving and very generous and humorous. And that's just my experience. But his podcast, I love. And it changed my life. It changed the way I look at things because he owned up to the way he behaved. And I listened to it and I said, two things, man, that sounds a lot like me. You know, he's a guy that got fired and he was gone from the business for 11 years until he finally got brought back. part two of that was
Starting point is 00:41:39 I wish I'd listen to this podcast while I was at Fallon because there was a lot of warning signs and can I interject real quick though? Bruce Pritchard admittedly brought a gun to a tape. I never did that. I never did anything like that.
Starting point is 00:41:54 But you know what else you don't want to do is if there's someone who has a very close personal relationship with the person that makes the final decision and they're really good friends, you don't want to piss off that friend. and that's what I did. And, you know, then when you do that,
Starting point is 00:42:12 all the stuff you've done in the past comes back to haunt you. And so I was stupid, you know, like for me, it was less like doing anything. You know, I never brought a gun to work. I never, it's funny because Jezlinix joked about that. Is that fair that I mentioned that about Bruce? I don't want to. I think it's fair.
Starting point is 00:42:29 Yeah, I think it's fair. But Bruce's big thing was he didn't get along with Stephanie McMahon. And he was in his words, I think, He said he was immature about it, and he was not communicative, communicative. And it was inevitable probably that he was going to be let go anyway, but that was something. No, he gave her the smoking gun literally and figuratively is what all she needed, but it was a very similar story to what I went through. But yeah, that's what I tell people is that, yeah, you're invincible until they hire someone
Starting point is 00:43:00 that knows that has your number. I do want to mention that I don't know the circumstance with him bringing. the gun. I don't know if it was I'm guessing it was unloaded. I think that's what he said. I believe he said it wasn't loaded. I don't know if he was aware it was even there. There was a hurricane or there were storms or fires or something down near Houston, Texas, where he
Starting point is 00:43:21 lives, I believe. And I think in packing up he went straight on the road and packed up all his stuff and ended up bringing it to the show unwittingly. And I think or was trying to get rid of it or something. I don't know. exactly it's on something to wrestle it's on his podcast why was bruce fired which is probably the best episode they he and conrad have done um but he talks about it there he owns up to it yeah he did that i never did that but yeah but i will say that you know i like i had that reputation with
Starting point is 00:43:55 certain people in the office that you know yeah i was the dwight shrewd i was the guy that was going to go nuts someday you know so it's like i never did anything like that but you know i like I said, I was the ticking time bomb. And I think what no one realized was it was going to go off internally that I was going to implode instead of explode. And, you know, that's ultimately what happened. And you did go to therapy, correct? I went to therapy after it ended. I went through a real, real rough time. I mean, a lot of 2018, that's like my last year in a way. Do we want to talk about that now? We can. This is you're going through a divorce. You had just got and let go. from Fallon and one of your parents was sick?
Starting point is 00:44:40 Well, here's what happened. I would say I was more pushed out at Fallon than let go. There was no, there were people there, namely Mike DeSenzo and supposedly Gerard Bradford, but I can tell you Deach for sure that were fighting for me to, that were like basically saying to Amy Olzels, who was the new head. had writer that you can't fire Rydenman. You just can't. We're not going to fire him.
Starting point is 00:45:09 She had Jimmy's ear. She was the Stephanie McMahon of the situation. And it's so funny I said, because I'm friends with Stephanie McMahon. I love Stephanie McMahon. But Amy was wanting to get rid of me. And so it was sort of this, you know, just keep writing for the show, but you can't come to work anymore. She had been let go, though, right?
Starting point is 00:45:28 And then brought back. Is that what happened? I could, I just want to make sure. Dude, she's, she's been, I think she's been. I think it's happened two or three times. Yeah, she got let go one time that I know of in 2013 as showrunner. From Fallon. Yeah, they brought Josh Lieb in instead.
Starting point is 00:45:48 Then they bring her back and then she asked to have dinner with you. Yeah, they brought her back and I always thought I was cool with Amy. I wrote a pilot with Jimmy and Amy about wrestling of all things back in 2012. And we got real close to producing that thing. And a couple of things happened after the fact where, admittedly on my part, where I think I f***ed things up with Amy to begin with was, this will sound insane now because it's like ancient history.
Starting point is 00:46:22 It's like you're like, what? But we pitched the show to USA after NBC had passed on it. And USA didn't want to do the pilot. written with Jimmy and Amy, but Chris McCumber, who was the president of USA at the time, wanted to do a different show with just me. And so I basically used that meeting that Amy had set up for me unwittingly, but sort of, I kind of let it happen. I kind of turned a blind eye and cut a handshake deal with Chris that let's go do something different without Jimmy and
Starting point is 00:46:58 Amy. And to no one's surprised by like two days later, that thing was mother fucking dead. I mean, that was dead in the water. Because as soon as Amy and Jimmy caught on to that, all of a sudden you get the call from Chris, ah, you know, I think I spoke too soon. And I don't know if we can really do anything else. And okay, you know, it goes away. And then the flip side of that is now you got your friend mad at you. You know, Amy's mad like, man, I got you that meeting. And you didn't even come to me to ask, you know, like, what the hell? You know, because the ethical thing would have been for me to say to her, hey, Amy, they don't want to do Slam, but they want to do this
Starting point is 00:47:33 other thing. Would you want, you know, come do it? Like, you know, we'll all work together on this thing. And I didn't do that. I was young. I was immature. I didn't understand the business. And it pissed her off. I didn't know that it pissed her off. And then in 2016 or 2017, out of the blue, Amy is sort of in the picture again. She's writing jokes. Like, I first realized that when Jimmy was doing Dennis Leary's fundraiser in Boston and I got there and the monologue was totally rewritten. I had written his monologue for him that he was going to go up and do stand up at Dennis's fundraiser. And I go, what the hell? And I go, why is this all different? And I go, who wrote these new jokes? And he goes, Amy Olsles. And man, when I heard that name,
Starting point is 00:48:18 heard Jimmy say it too. Because like when she got let go, that was a big deal. And it was like, you didn't mention her in the office and you didn't mention. her to Jimmy. If he had a story to tell that it mentioned Amy, fine, you didn't bring that name up. It was almost like bringing up an old writing partner or someone, you know, it was like a Farrell McKay sort of situation. And all of a sudden, she's back. And when I heard she was coming back to behead writer, I loved the idea. I loved it. Like, to me, it was great because I felt like she didn't get a fair shot in 2013. I loved that she was coming back. I felt like a great redemption story. Yeah, and then she asked to have dinner with me, and during the dinner made it very clear
Starting point is 00:48:58 that she thought I should leave and just ask me, you know, why don't, why don't you go do something else? Why don't you develop a pilot with Lorne? Why don't you go do this? Why don't you go do that? And when she's saying this to me, this is right after I finally, after all these years, fallen in love with the job in the show. And I had let that anger go. And I had really, you know, I had a daughter, you know, when you come home to a daughter and she comes up and crawls across the carpet and gives you a big hug and you're trying to get things right with your wife and everything, you let that work anger go.
Starting point is 00:49:34 But now it's like right when I've fallen in love with it, she's saying, why don't you leave? Yeah, shortly they're at that night, as a matter of fact, on the way home is when I passed out on the subway. It was the mini stroke. the mini stroke and then all of a sudden it was like I just couldn't write anymore like I could read people's jokes I could edit I could put together a mono but I didn't have the same brain for several months to write and then Amy came into the office so now I'm trying to manage up a little bit too which I had not had to do like the reason it had been so much fun is that it was just being Jimmy
Starting point is 00:50:09 like I was I mean you know at first it was very difficult you know there are stories that are out there that they only really have half the story or a third of the story. But there's some that I hear and I go, I remember that. Like I was, I was part of that or I got it pretty bad that day. And it was tough with him at the beginning. But then once he trusted me, it was fantastic. And I could email him and say, hey, Jimmy, I don't have an opener. Every opener I have here is really dark. It's either going to be about Trump or it's going to be about Matt Lauer or it's going to be about, you know, Charles Manson. Like I just like I don't know. And he would write back, don't worry about it. We'll figure it out. It's going to be great. And it was
Starting point is 00:50:49 amazing. And it made me feel so good. Then all of a sudden, Amy's there, and I can't talk to Jimmy anymore. And it's like anything that said to Jimmy, I got to go through Amy. I noticed that after I had that dinner with Amy, Jimmy didn't really talk to me anymore. And if you watch, to go back to the wrestling theme, the 25th anniversary or whatever it was, a Monday Night Raw from the Barclays Center. Yeah, it's Raw 25. The four of us are sitting there, a ringside, and Jimmy and I are on different ends. Jimmy purposely made sure Gerard and Amy were sitting between us, and he didn't talk to me the entire show. So, I mean, this is, we both, we wrote a wrestling pilot together. We both loved wrestling. We talked about it all the time. And that night, when he didn't talk to me at all,
Starting point is 00:51:39 I was like, uh-oh, something's off. And it was really just a harbinger of things to come over the next couple months. So that was sort of the beginning of the end. There is a lot more drama that I would love for you to come back. I mean, I have three pages of notes still here from things that I want to ask you about. I do want to mention, we talked about the last time your book is out. It came out in June. That is the garden is always greener.
Starting point is 00:52:06 I know also you got a blur from Jay Leno. the last time Gary Gullman, Wayne Federman. So that is out now. Real quick, just talking about the, you love the Celtics. And I know this is a basketball writing about basketball. What was that like working with Larry Bird when he came on Fallon? So that came. That was thanks to Gerard Bradford.
Starting point is 00:52:30 He's the one that made that happen. We had a story around Thanksgiving that the bird flu was out. And everyone had to be scared of the bird flu. can you imagine that a pandemic unbelievable so this is 2015 and i said to gerard you know it'd be really funny is if we said there's a bird flu uh let's check in on it right now how's it going larry and we just cut to like larry bird like sneezing and then he goes that's actually really funny i go yeah yeah yeah because i think he's gerrador's always ribbing me he's the same guy that convinced me that all the malls close down in new jersey on the weekends and dumb
Starting point is 00:53:03 shit like that and then i'd go home and yell to my wife she'd be like that's not true and then Gerrivers be like, you fucking idiot the next day. But so I thought he's ribbing me. Like I'm like, yeah, right, whatever. So I get an email from Risa Abrams, our writer's assistant and producer, by then I I think she's producer, the coordinating producer. We got an email from her next day saying, hey, Larry Bird said yes. And I'm like, yes to what?
Starting point is 00:53:26 And she's like, isn't it your bit? And I'm like, wait, Gerard, like, you guys really redid this? And she's like, yeah, we reached out to the Pacers. And she goes, he called back 20 minutes later and said he'd do it. So we go in and it's on. Skype and Larry wants to do it at 8 a.m. his time, 9 a.m. R time. Sharp. Larry Bird is Larry Bird. He's ready to shoot early every day. And so we go in there and the screen comes on and there's Larry Bird.
Starting point is 00:53:51 And he has one line where he's got to say, he's go, you know, how you feel on Larry? And he goes, not too good, Jimmy, go Pacers. So he does it the first time, it's great. Like we could get out there. And then he goes, let's do it again. I think I got something for it. Let's do it again. So he says line again. he sneezes it does something else and goes like go pacers and we got we're like larry thank you so much he goes one more time let's run it back one more time boys and we're like all right and then he gets he gets the larry bird game face and then he goes not so good jimmy yeah go pacers and he says
Starting point is 00:54:26 it like a twink he makes his eye twinkle somehow and somehow it's perfect so it's like we're all just like oh my god so you know chris tataro says thank you Larry, that was great. Chad Wallet says, you know, Larry, that was, you know, Natalie Byrd. Thank you. Thanks for coming on. Gerard says, thank you, Larry. It was great. And everyone looks at me. I'm the last one. And Larry turns his head to me. And I go, this is day before Thanksgiving, mind you. And I go, Merry Christmas, Mr. Bird. And he goes, he kind of pauses and then just click, turns off the sky. And I'm like, oh, we have all. had that happen to us. But dude, by the time I got, Gerard must have called her or sent her an email
Starting point is 00:55:13 or something. By the time I got home, Rebecca just goes, Merry Christmas, Mr. Berg. I'm like, oh, how do you now? And she goes, oh, I heard. Everybody, everybody knows. Our neighbors knew. It was horrible. Like, it's so I said, and people say, how was it meeting Larry Bird? I got, it was great till I met him. It was great till I talked, you know, but he was, it was awesome. He was, he was a real pro. really funny. So he's cool. I'm glad that you had that. Will you come back again? I'd love to. We have to do this to conclude on how everything went down with you and you built your life up and the correspondence dinner and then you doing stand-up on the show and you almost injuring Lauren Michaels. Oh, yeah. I mean, we have a lot to talk about that. That would be great.
Starting point is 00:55:58 Thank you so much for being on again. Thank you, Mark. Garden Screenerbook.com. Go get it. Thanks for listening. Please subscribe so you never miss an episode. On Apple Podcasts, please rate it and leave a review. Be sure to go to late-nighter.com for all your late-night TV news, and you can find my podcast at late-nighter.com forward slash podcasts. Have a wonderful week, and I'll see you next Tuesday. We're going to be.
Starting point is 00:57:02 I'm going to be. Thank you. Thank you.

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