The Bill Simmons Podcast - A Sox–Yanks Power Flip and Biden's Struggles With JackO, Plus Sean Penn's First BS Appearance

Episode Date: September 11, 2019

HBO and The Ringer's Bill Simmons is joined by his buddy JackO who gives his thoughts on the Red Sox firing their GM David Dombrowski, the surging Yankees, the Democratic presidential candidates, and more (4:10). Then Bill sits down with Academy Award-winning actor Sean Penn to discuss his long career, his new novel 'Bob Honey Sings Jimmy Crack Corn,' what he'd learned from Clint Eastwood, Jack Nicholson, and David Fincher, and more (33:08). Learn more about your ad choices. Visit podcastchoices.com/adchoices

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Play NBA 2K20 today. NBA 2K20, welcome to the next and welcome to me because I'll be popping on your game as you're playing. All of a sudden you're hearing my voice and think you're hearing a podcast or something. We're also brought to you by The Hottest Take. That is our exclusive daily podcast that's going to be on Spotify starting next week, September 16th. You can

follow The Hottest Take on Spotify. This is an idea we've had since 2015. Chris Ryan wanted to do a game show with The Hottest Take where we had judges and we talked about that. We tried to figure out different incarnations and we never kind of figured it out. And then we finally figured it out. We decided it would be fun to take the hottest takes we've ever considered, takes we don't even necessarily believe and argue about those takes like we really did believe them. But do we actually believe them? I don't know. That's for you to decide. That's the hottest take. And a bunch of the people who have been on this podcast and on the Ringer Podcast Network in general are going to be coming on and delivering takes. Here's the

little catch. It's a short podcast. It's going to be between six and nine minutes, depending on the podcast. So it's a little quickie, a little way to start your morning. All you have to do is go to Spotify and subscribe to The Hottest Take on Spotify. It's exclusively there. And there you go. All right, we are taping this part at six o'clock PT, West Coast time. We'd actually finished this podcast

and we're putting up later tonight. And then a story broke, courtesy of the New York Times and TMZ, that New England Patriots receiver Antonio Brown had been accused of sexual assault on three separate incidents by a woman named Brittany Taylor, who is somebody that was working as a trainer for him. The details are pretty horrible. And a lawyer representing Brown, Darren Heitner, released a statement saying that Mr. Brown denies each and every allegation in a lawsuit, etc., etc. And until we find out more about this story, which again is really horrible, I don't feel comfortable talking about Brown on the podcast. So I had my buddy Jacko. He came on earlier today, and we talked about the Patriots at the top as well as the Red Sox and where the Democratic Party is standing right now, and then it goes to Sean Penn after that.

But until we find out more about this story with Brown, I'm just going to take that Patriots part out, and it's going to jump right to the Red Sox. So let's see how this story plays out. Here is my buddy Jacko and we are going right to the baseball part. I couldn't, I couldn't stop thinking how we had to talk on a podcast at some point this week.

You love nothing more than when this Red Sox ownership, which has won me four world series. So I'm going to tread carefully. A has a scapegoat. ownership, which has won me four World Series, so I'm going to tread carefully. A has a scapegoat, and then B jumps on some sort of media manipulation narrative

in some way. And they really peaked on Sunday after yet another embarrassing Yankees-Red Sox series. Sunday night, the Patriots have just made one of the craziest Boston signings in recent memory. Most unexpected. Oh my God. It's definitely one of those, like even people's moms knew about what happened that don't follow sports. And on top of it, the Patriots are kicking the Steelers

ass on Sunday night. So Monday, Tuesday is just all going to be Patriots locally. Nobody's going to care about anything else. And at midnight, the Red Sox are like, Hey, we fired her. We fired her GM. It's not going to be her anymore. Well, isn't there a conspiracy theory that John Henry hates the Patriots? Or isn't there some bad blood between like John Henry and the Globe and the Patriots? Yeah, there's always been rumors.

Yeah, the WDI and all that stuff. Isn't it a thing that he did this to step on their banner ceremony and the Antonio Brown. Yeah, there's always been rumors. Yeah, the WDI and all that stuff. Is it a thing that he did this to step on their banner ceremony and the Antonio Brown thing or whatever? No, I think it's the opposite. I think they knew they were doing this anyway. Like a Friday night news dump. Oh, it's the all-timer. This was, what was the one where Nixon fired all the-

The Saturday Night Massacre. The Saturday Night Massacre. Yeah, yeah, yeah. This was the Saturday, it was the Sunday Night Massacre. The Saturday Night Massacre. Yeah, yeah, yeah. This was the Saturday. It was the Sunday Night Massacre. They did it. I woke up and I had gone to bed because I'm old. And I woke up the next day and I turned on my phone.

And I was looking at Twitter and it said, you know, part ways with Dombrowski. And I was like, wow, I couldn't believe it. Because, I mean, the guy won 108 games in the World Series last year. And so to blame it on Dombrowski, like, what, did he take John Henry's checkbook and he was, like, doing all these things without their knowledge? Yeah. Like, you know, he signed Steve Pierce to an extension and gave more money to Porcello and Sale and side priced at $217 million. Like, did nobody else sign off on that? That was, like, all on him.

And to blame this year on him. I mean, they didn't bring back Kimbrell and they didn't bring back Joe Kelly, but the rest of the team was the same. Like, I don't understand what was his fault. I mean, he's been doing, this is like what his, you know, his, his thing is that his, his resume was that he goes out and signs guys and he burns the farm system to get guys in, but they won the world series last year and had the most wins in the history of your franchise. And then they can the guy at midnight, and then they don't have any kind of a press conference or anything.

And they only have about 47 different, you know, executive vice presidents, and they make poor Alex Cora have a press conference where reporters question him about it. And he's like, I didn't fire anybody. He's like, yeah, I just found out. Sorry guys. I mean, for an extremely successful ownership group that, you know, turn the franchise around, they do some things that make you scratch your head sometimes. Like, I just don't understand why it's his fault. And then you don't come out and explain what your rationale was behind it. So there were a lot of rumblings all year, even after they won the World Series,

that it was a very weird dynamic over there. And Shaughnessy, for the Globe, had a piece about a month ago. He's pretty wired in the Red Sox side with a couple different people. And he had some piece a month ago about basically tipping it off that there was a weird thing going on

where he only had Tony La Russa and this other guy as his right-hand people and didn't really interact with anyone else and was just presenting himself as the aloof enigma, which you can do when you have the best season in Red Sox history, but it's harder

to do when every single move you've made during an entire year of 2019 was probably the wrong move. Yeah. He did the pro I had friends. I was just excited to get baseball texts from anybody other than you and my buddy Hench and my dad, who were the only three people that even text me about baseball anymore. But I had friends that were like, wow, that guy just won you the world series. What happened? And it really comes down to, he just spent a lot of money after they won the title,

but seemed to not realize that by doing that, they're now going to have to choose between Mookie Betts and JD Martinez. Right. But I mean, yeah, anybody could have known that though. I got to say, I didn't know that last year. Like when they gave Evaldi that huge extension, I was like, great. It's not my money. He's a world series hero. Glad he's back. And if he blows out his arm, so be it. But I didn't realize like, Hey, by doing the sale extension and by doing Evaldi, we're going to have to choose. It's going to be Sophie's choice between JD and Mookie in the next off season. I would not have signed off on that. Well, isn't the problem that, really, that Mookie bets after the Trout contract basically came out

and said, or his agent did, that he wants Mike Trout money? He deserves it. Yeah, but they're not going to give him that. They're not going to give him Mike Trout money with all the other money they have tied up. Yeah, but he deserves at least... And account on J.D. Martinez to opt out.

What if he doesn't opt out? I mean, I made a joke on Twitter about this, you know, he's going to get a phone call and he's going to say it's Bob Holler from the Boston Globe. Oh, yeah, they're going to smear him? Where they try to dig up some dirt to run him out of town, which I wouldn't put past them. He's going to have the old Terry Francona profile treatment? Exactly.

J.D., it's Bob Holder from the Globe. Can you comment on your four mistresses thoughts? JD, I was searching through your locker yesterday. All due respect to Bob Holder. He wrote the Terry Francona piece that had a lot of sources. After they ran Terry Francona out of town. Yeah, it had a lot of sources. He was the guy that dragged him through the mud, right?

I mean, it's his job as a reporter, if people are telling him stuff, to write the stuff. It's just that everybody had a clear agenda with what they were telling him. And, you know, I just think he did a really bad job this year. And it was obviously not happy behind the scenes to begin with. But you talk about the sale extension, which Hench and I went nuts when that happened because we were like, that guy just basically couldn't get through the last two postseasons.

Can we see another year first? Yeah. Is it okay if we can make sure he can pitch six, seven straight months? The guy loved his players. He wanted to be loyal to guys that won the most games in Red Sox history and is paying you back for past service.

Well, the other... The Kimbrel thing I supported because that guy was a rollercoaster ride and I did believe in the whole bullpen back committee thing. You don't need a closer, right? Yeah. It also didn't work. And as the season went along and as that became one of the

Achilles heels of the team along with the atrocious starting pitching, they just kind of didn't do anything. And the big move was Kashner. You faced Kashner during some of these Yankees games. Any fear of Kashner at all? No. I looked lustily when I saw his name in the box score as facing the Yankees happily.

There was just not a lot of scrambling, especially as the bullpen started to get wore down. If Darwinson Hernandez hadn't come in, who's my favorite Red Sox pitcher, if he hadn't kind of emerged out of nowhere, they really would have been in trouble because they didn't have anybody like that on the team. Then Workman kind of became a pseudo decent closer.

I don't trust it, but at least he was competent for two months, but that bullpen could have been worse. It didn't do anything. Everyone else was doing something and they didn't really have a lot of prospects to trade either, which cause they had already traded a lot of them. I still think the sale trade was a really good trade

and the guys that came up that they gave up. You still do that. Nobody set the world on fire yet. Yeah, you give up three major prospects, odds are two of them

aren't going to make it. You know, and for... and the guy was, you know, one of the best pitchers, well, maybe not now,

but he was one of the best pitchers in the American League. He won your World Series. You can't question that trade. That was worth it. My biggest, now this has happened before they won the World Series, but I'll never understand how he missed on Verlander, who he was with, and the Yankees too.

The Red Sox and Yankees missing on Verlander is kind of inconceivable because it just wasn't an overwhelming amount of money. And the book on him just seemed to be like he was done and that he was headed toward another point of his career. And it's been the complete opposite. I don't know how both of those teams missed that. Two teams that needed a guy like that. Well, I think the Astros might have a little Patriots in it when it comes to pitchers.

Oh, no. The Atlanta Pilates? I think there's a little Patriots in it when it comes to pitchers. Oh! No, not a lot of Pilates. I think there's a little something going on. Come on. I've seen things about the spin rate. Verlander didn't look like he was done, but he's not the Verlander of today. So I have a few questions. The organization that had Mike Scott, too, don't forget.

I'm not saying he's got the same paper on his mouth. God, you're just accusing everybody. This is terrible. Well, I'm getting ready for the playoffs and hopefully a showdown with Houston, so I'm throwing down the gauntlet already. They do. They do have a specific thing they look for with pitchers

that they just hammer home, right? With certain pitches and... The ability to wheeze pine tar or something, something shady there. I love it. You really are in playoff form. You've eliminated the Red Sox. Now you're ready.

You've targeted the Astros. I'm stepping over your dead carcass and I'm moving on to Houston. That's where all my focus has to be. Well, this Red Sox thing, the full concept of a five-year grace period. I think the internet has basically ruined it. There is no grace period anymore.

108 wins and see you later, right? Enjoy the ring. Get out. My whole thing is, the more I thought about it and the more I watched the team this year, like Belichick would not have signed a Valdi in price. He just would have been like,

thanks guys. Right, absolutely. I have a parting gift for you. That's the mentality for Belichick, right? Belichick absolutely, one million percent, would have traded Jackie Bradley Jr. last winter. Yes.

He would have done that in five seconds and put either Betts or Benintendi in center and just kind of figured it out as it went along. And I think Belichick would have tried to lock up Mookie even before this became a thing about his contract because he would have been worried that it would have weighed on him. He just would have tried to take care of it in some way. Here's where I stand, though. As long as they have Devers, Mookie, and Betts, and JD, and Benintendi, I'm not going to give up on, but let's just say you can get his stock right now.

It's available. He regressed a bit. It's available. Benintendi's stock is available on the internet. But just with those four, you should just be a 90-win team. Yeah. It's amazing, really,

when you look at their roster and their talent and they always seem to be, now they've kind of packed it in, but for a good portion of the season, they were never out of games with that offense. Yeah. And there'd be times I'd be flipping back and forth between the Yankees channel and the Red Sox channel.

And you know, they're down big and I'm like, Oh, this is good. And then you turn it back and they're like only down a run or whatever. They're still in it. So with that lineup, it's amazing really that their record is as mediocre,

is as mediocre as it is. World Series hangover, I guess, whatever. It was that, really, that their record is as mediocre as it is. World Series hangover, I guess, whatever. It was that, but it's really the pitching. Yeah, the starters weren't good enough and the bullpen was horrible. Yeah, it's funny because everybody blamed the bullpen, but the starters were equally horrific.

Their staff ERA for most of the year was like 4.8, 4.88, something like that. Now it's down a little bit to 4.7. But they were just giving up five runs a game. It's really hard to win when you're doing that. And then they were losing a lot of those tight ones that,

as your team has shown over and over again, your team in a close game, you feel like, oh, this is great. It's 3-3 in the seventh. We're winning. We have five relievers we're going to trot out. We have a bunch of guys having a career. Boy, you want to talk about candidates.

There's a couple on your team. How about your dude, Gio, who's one of the best hitters in the American League who hit like 210 last year? Hey, he was a diamond in the rough. Undiscovered gem. That's what Cashman does. Is that what he does? They have a brilliant analytics department.

Oh. They're going to swing, change things up. Yankee Stadium, more friendly confines for him, you know? You have MVP DJ? DJ LeMayhew, right. Is he an MVP?

Is he an actual MVP candidate or no? He should be, yes. He's not going to win it because Trout's going to win it, but he legitimately is. He's legitimately the Yankees MVP. He's been humongous for them. Is Mike Trout really going to win the MVP again? Yeah, probably unanimously.

He's made a big difference because without him, they would have only won 67 games instead of 77. No, they have 67 wins right now. They're 67 and 78. Oh, so I guess without him, they would have only won 67 games instead of 77. No, they have 67 wins right now. They're 67 and 78. Oh, so I guess without him, they would have only won 57 or 50. So that's good. It's great.

Hope he enjoys that contract and always coming in, you know, 20 games behind the Astros or the A's. Good luck with that. I don't understand how somebody can be the most viable player if their team doesn't even go 500. Where were they?

Yeah, I didn't get that either. What was their value? That the team, instead of sucking really hard, just sucked? Right.

Say, man, if we didn't have Trout, man, we just would have sucked. Right. Instead, we just sucked. Right. I don't understand it. Yeah.

They should just have, they need to create another award so there's some way to capture what actually happened this season over just like the here was the individual player of the year

just change it to player of the year because the whole notion of MVP which you know goes back 100 years or whatever like it's not voted on

as the most valuable to their team but keep that keep most valuable just have another award for like our individual player of the year or so and so.

He's going to win it. Everybody says it's unanimous that he's going to win it again. It's like in the Oscars, the nominees are Keanu Reeves for John Wick 3 because without him, instead of a B-,

that movie would have been a D minus. He had an unbelievable war. I don't get it. That's right. So your team, you have a chance to win a lot of games. You're 95 and 50 right now. You put like a puncher's chance to win 110 games. You had an incredible amount of injuries.

But the big thing, and I only know this because he's on my fantasy team, was he got Judge going again on top of all the other guys. He's been really hot the past couple weeks. That's huge because he was looking lost there for a while, but if he turns it on, if he, in the postseason like he's had it going on now,

they're legit dangerous. And Paxton looks good now again. And Tanaka, aside from the Red Sox, has looked good of late too. So, and all of a sudden, Jay Happ was great the other night.

That was just worries me. Don't trust him. Jay Happ's back. He'll start a game and give up 15 runs in two innings. You just have to make sure Paxton stays healthy

for another eight weeks. So you have a 50% chance. Kyle, I'm going to ask Kyle. He's young. He's a-something. How many years do you think it's been since the Yankees won a World Series? He barely follows baseball.

Not barely. Did they lose to the Marlins? Did that happen? That did happen. That did happen. That did happen, yes. Was it 2008, 2009? I don't know.

2009. 2009. It's the 10-year anniversary of Jacko's last World Series. A full decade of no World Series for you. This is ridiculous. Did you even make a World Series this decade? Did you? 2009 is their

last appearance, I believe. They're 0 for the decade. It's unbelievable. No wonder you were taunting the Red Sox on Twitter about being eliminated. is their last appearance, I believe. They're 0 for the decade. So far. It's unbelievable. No wonder you were taunting the Red Sox on Twitter about being eliminated. Absolutely. I've got to have something, you know? I've got to start somewhere.

So when you look back at the highlights of this decade for the Yankees, is it like a really strong ALDS game? This is outrageous. What do you have on your DVR? Just like the 2014 AL game? This is outrageous. What do you have on your DVR? Just like the 2014 ALDS? This is outrageous. I'm not even going to respond to this.

I'm not going to dignify this with a response. The best thing about the Red Sox-Yankees rivalry is that when one of us isn't in it, we still have a team that's in it because the team is basically anyone playing the Yankees or the Red Sox. Of course. that's in it because the team is basically anyone playing the Yankees or the Red Sox. And now, so people are like, hey, Bill, you had a great last 15 years. You won four World Series. It's got to be weird not to have your guys in there this year. I'm like, well,

I have all the guys playing the Yankees. I have everyone else in the American League. It's actually, this will be fun. You'll be all in on the Rays or the A's or the Twins and then the Astros and God willing, the Dodgers or the Braves or whoever, yeah. I mean, you know,

when you win four in 15 years, you start getting used to it. You know, it's like getting scrambled eggs every morning where you just kind of take them for granted

and then one day you're out of eggs. Kind of look around. When you win four over a course of 103 years, of course, it's really going to be memorable for you. I don't know how you measure this stuff, but I measure it by this century what's happening. I can't worry about last century.

Last century is in the books. It already happened. I just think about it as this century. What about the present day, though? What about this year? Well, you're looking pretty good. Yeah,

there you go. Who are you afraid of? I'm not here to talk about the past decade. I'm here to talk about now. I'm not here to talk about the past decade. I'm not here to talk about the past decade. I'm here to talk about now. 09 was when the Yankees won the world series.

And then on my podcast, I sneak attacked you with this rant you had about Marian Rivera that you got mad at Marian Rivera in May. And you were genuinely mad at me. You were mad. I knew you were mad. No, you were mad. I could tell you were mad on the phone.

I was like, oh, God, I made Jacko actually mad on a podcast. No, you did not. It was all in good fun. Marianne's rant is legendary. My rants are really legendary. Nobody likes me when I'm happy on these podcast. No, you did not. It was all in good fun. Mariano rant is legendary. My rants are really legendary. Nobody likes me when I'm happy on these things and gleeful and cocky. The rant was great. It was good.

It's good for my brand. I went to a Metallica concert on Friday night in San Francisco. Yeah, I did. I hated... It's a long story. I used to hate Enter Sandman forever. go yeah I did and I hated it's a long story and and I used to hate

Enter Sandman forever because it was the Rivera it was like the it was like the the sound of death it was like you're down

a run you're down two runs and then that fucking song it's like alright pack it up let's might as well go to the car right

and then everything flipped because I don't know if you remember but he blew the save in game four and game five of the LCS now it And then everything flipped because I don't know if you remember, but he blew the save in game four and game five of the LCS.

Now it's a song that makes me happy. I actually like hearing it now. It brings me to a happier place. Speaking of happier places, before we go, can we get your thoughts

on where the Democratic Party is right now? Well, it's a good question. I mean, poor Joe Biden. like, you know, they're making him run for president and he gave a, because he's got, he's the most electable, I guess, on paper. And he gave an interview to the Washington Post, I believe it was either New York Times or the Washington Post. And they're both fake news. Can't tell them apart, whichever one it was. And

they're like, you know, basically why you're running for president. He's like, well, I didn't expect to, you know, I didn't really want to, but I guess I have to. And it just makes, you know, all these gaffes and he's out there and he's confused. He keeps calling Angela Merkel, like Margaret Thatcher. It's like really like terrible. So I don't, I don't know if like Elizabeth Warren, who's the media darling and the darling of the left wing, you know, she's a semi more electable Bernie, I guess, because she sort of steals all his positions.

I don't know if she's going to be able to catch him. I think that's where the heart of the Democratic Party is, but I think their head is with Biden. So I don't know what's going to happen. I mean, there's some polls out now where he's he's kind of weak in New Hampshire. And, you know, she's a senator from a neighboring state. So if he doesn't win in New Hampshire, and I don't know if he's really beloved in Iowa, and he loses in Iowa, and all of a sudden you're a frontrunner until you start getting wounded. And when you're wounded, you're not looking that electable anymore. He could tip over pretty quick, and it might be like, it might be red for the exit time for old Joe.

So I don't see Elizabeth Warren winning a national election against Trump, but I've been wrong before and I could be wrong again. So I think Biden could beat him. I don't know that Elizabeth Warren can. Do you think he's going to stumble in New Hampshire because he thinks he's in Vermont? Well, he did think that already. I mean, that's really like, that was really like eye opening and shocking, quite frankly, because while in a normal, any other time you could maybe confuse New Hampshire and Vermont, they're next door. They're both, you know, rustic, rural New

England States with low autumn leaves and maple syrup. You could confuse that, but everybody on the earth, like my eight-year-old daughter knows that New Hampshire has the first primary in the country. So when you know you're campaigning presumably in the first primary state and not in Vermont where you wouldn't campaign for any reason, I don't understand how you could confuse that. That was really troubling. It's not great. It doesn't bode well for Joe. There's been a lot. And it was like at this debate about climate change last week.

And all of a sudden his eye was bleeding. See that? No, I didn't see that. Oh my God. It's some sort of thing where it's like, I don't know what it was from, but his eye was bleeding. And he just always looks like he's half out of it. And, you know, the guy's 74 years old. You can't blame him for being out of it.

And it's rigorous to be on the campaign trail. It's a young person's game generally. Of course, every Democratic frontrunner is like 80. But, you know, he's really like made a lot of mistakes and gaffes. Of course, you know, our current president is not exactly a great wordsmith. He's gaff-free. So, you know, that's going to be a fantastic debate. I made a joke about they should just give them a puzzle and the winner gets to win the debate, you know, but they start a joke about, they should just give them a puzzle and the winner gets to win the debate, you know, but,

uh, they start a clock. Okay. First one to finish this puzzle. They're like, Oh geez, start with the corners. You know, um,

it's troubling. It's really troubling. You know, uh, my dad was on my podcast Saturday, who's three years younger than Joe. And he called Demarius Thomas Demetrius four times during the podcast. Now I love my dad and it doesn't mean his brain is super slipping,

but if he was on the campaign trail, that kind of stuff would be happening every day. And I just think with Biden, it's going to get worse, not better. He's already had so many little minor slips and screw ups and whatever. And we're not even really in the rigorous part of this whole campaigning thing yet, where you're on the road for a year, you start getting worn down physically. And I'm with you. I actually think this could go south pretty fast. What's funny though, I'm looking at on Sportsbook, the odds to win the next presidency. And now Elizabeth Warren is the second favorite.

Trump is still minus 110. Warren's four to one. Biden is now six to one. So he's not even the favorite. It starts taking on water like that. If you're the front runner and you get wounded, it happens pretty quick where all of a sudden it's like, look at Howard Dean. Yeah.

You know, Howard Dean was leading in all these polls. Everybody loved him. And then, you know, where was it? He lost in Iowa or whatever and fell apart in Iowa. And it was like, that's all she wrote. It happens quick and the media will turn on you at a time and they start to see the new, you know, hot candidate. And they will gravitate towards him or her. And that's going to be all she wrote for old Joe.

Then Joe's 6-1. What's crazy is Andrew Yang is 15-1. Andrew Yang is not going to be the president. Bernie Sanders is 18-1, and Kamala Harris is 20-1. Booker's 75-1. Wait, Andrew Yang is 15-1, and Bernie is 18-1?

I'm just reading you the odds. That's ridiculous. You think there's been money from the Yang gang trying to juice his odds? There must be. The Yang gang must be betting odds. That's ridiculous. You think there's been money from the Yang gang trying to juice his odds? There must be. The Yang gang must be betting heavily. That's ridiculous. There's no way Andrew Yang is going to be president. Yang gang's an NBA fan.

Yeah. I think we should just call him Yang gang, not even call him Andrew Yang. He's just Yang gang. Andrew Yang's this guy. I know he's like a tech entrepreneur or whatever. Yeah. He immediately is like, I'm going to just run for president. Can you run for Congress first? Can you run for president. Can you run for Congress first?

Can you run for Senate? Can you run for city council? Just follow the Trump model. Right. But Trump is unique in more ways than one. But I mean, Trump's a celebrity figure and a developer and had a national presence.

Nobody knows who Andrew Yang is that you're just going to go from being a tech entrepreneur to being the president. It's just not going to happen. Well, I was thinking, tell me if this is completely inconceivable Trump would do this. Don Jr. decides to run as a Democrat for president. Okay. Trump gets all his people to now Don Jr. screws up the whole Democratic side.

And if Don Jr. wins, then Trump's just going against Don Jr. screws up the whole Democratic side. And if Don Jr. wins, then Trump's just going against Don Jr. for the election. He wins either way. He's grooming him anyway. I don't think you'd get a lot of Democratic primary voters to go for Don Jr. You don't think so? I don't think they'd buy that heel turn. But if he doesn't win, which he wouldn't, but he's still in the mix that debating all these people and screwing things up, it actually is kind of legal, right? You could do that. Well, yeah. I mean, in Vermont, I remember in Vermont years ago, Patrick Leahy, who still is their Senator, I believe. And he was running for office and there was a guy that was like this

farmer and this basically like this documentary people, I think they'd made a documentary about this guy who was this 80-year-old farmer in Vermont, Fred Tuttle, I believe was the name. I could be wrong about that. And they ran the guy in the Republican primary and he ran against some like stuffed shirt Republican. And this guy was a farmer and he kept talking about farming and they got enough votes to win the Republican primary. And then he was Leahy's opponent. And all he did was talk about how wonderful Leahy was. And they had these debates. And Leahy was like, I'm going to do X, Y, and Z.

And Fred Tuttle was like, right on. It was like, well, there you go. Sounds great. Yeah. Well, maybe that'll be what the Trumps do. We'll see. Johnny, we're going to definitely have you back a bunch of times over these baseball playoffs because-

Excellent. Hopefully, I'll be around for a while. Let's hope. Well, I'm just around for a while. Let's hope. Well, I'm just so happy for you that your baseball team actually has a chance to win the World Series. I know what that's felt like for me. And I'm happy I get to share that with you. So good luck

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at home. Go to onepeloton.com, P-E-L-O-T-O-N.com, and use promo code Simmons. That's my name to get started. One Peloton.com. All right. Not many people could get me to come in for a Saturday. This is one of them. They offer champagne. I'm just, I'm just taking it.

I don't care what day it is. Although if it had been Sunday football, I don't know. That would have been tough. Cause I don't even go to my daughter's soccer games during Sunday football. Nice to have you though. Good to be here. Um,

I David Spade on two weeks ago and we were talking about when you did the, the tattoo thing with him on SNL in like 95. And one of the great things that I loved about that was, it was like, wait, Sean Penn is funny. Does he, is, does he hide this from us? What's going on? Like there was this whole other side of you and I've always been fat and felt like you've been in my life my whole life, but there are all these layers to you, but the humor side is kind of the underrated layer

because that was Fast Times was basically your breakthrough and you were hilarious in that. Well, I'm not going to accuse myself of being hilarious in anything, but I do find myself ludicrous at times yeah and and uh yeah i i'm i i have heard from people that i've spent time with that um that that among the things i i subconsciously keep private is any level of humor i might have especially about myself yeah well you would you'd had the very starting like the mid-80s,

this guy's a serious actor. This guy, he really takes the craft to the fullest and all that stuff. But I always felt like, I mean, I know that was genuine, but at the same time, I always felt like you could have done, what, two more comedies?

Something like that? Did you ever turn down a comedy you could have done? That's a good question, only in the sense that I was offered so very few of them. Because you get typecast. Well, I think what happened, because I had done Fast Times at Ridgemont High very early on and so on, I think part of this quote-unquote serious actor impression people because what one does take hopefully what they do quite seriously and work hard to try to be better at it as you go along yeah yet at the same time as although anything was

being said whether it had been you know he's funny or he's, you know, brooding. Once you are being talked personally about or assumed to be something for the first time in your life in a public way, it is certainly going to be a one true part of you, which we said, and you don't want any more to be public. It kind of like, you know, there's always this idea that you want to take over, get ahead of the narrative. And I never wanted to get ahead of the narrative on myself. I just wanted to say, okay, this is what's assumed. I'll let them see that much. And I'll hold the rest for myself and use it as I will as an actor and maintain it in my life. But it was very, and still is, because I think, you know,

I'm a guy who didn't speak in public places at all, not a word, until after I was five years old. But I was very verbal in my family and a place wherever it was very comfortable. It wasn't as though I was unable to or couldn't string thoughts together, you know, five-year-old thoughts, though they be. But I think once that I was shy and to see other people get a degree of fame and have people talk about them, and certainly I had talked about famous people before I became someone that was in the public eye it's still I it once it was me it was like wait wait that no no no no no I didn't I didn't buy into this I want to be an actor but not this and uh it was kind of uh horrifying

well I'm sure it got complicated that you started dating one of the most famous people in the world at the time yeah that certainly certainly yes that that did complicate things you know further at that time yeah um going backwards you grew up as a hollywood kid your dad was a director yeah and you're rising up with this whole awesome class of actors that a lot of them became really famous. But Tom Cruise is in there and Rob Lowe and Charlie Sheen, Emilio Estevez. Who else am I leaving out? But you guys all knew each other. Well, yes and no.

I mean, all the guys you just mentioned are younger than I am. And I was aware, and I've heard stories about me and some of them that didn't happen because I hadn't met them yet. Some of that group, like the Sheen brothers, I knew them both as the Estevez brothers at the time. But Emilio and I were good friends charlie was very close with my younger brother yeah um which one oh christopher yeah and and and so them i knew but again i think emilio was one or two years behind me in school and you know at those ages those are significant differences and certainly from charlie's age or robowe, those guys, they were much younger than I was. But we came from the same place,

and then they started working, I think, soon after I did. And although Rob Lowe, I was aware of him in Malibu because he was a kid actor. Yeah. He was the only one that we knew of. But I didn't know him until years later. But you guys are all showing up for the same auditions and stuff like that right no i was all the uh they would have been you know it was that it was a significant that was like a five-year age difference between most of them

so no the people i was at auditions with would have been like you know kevin bacon in new york or or out here. Nick Cage, who was younger than me, but he was starting around the same time. Helen Hunt, I used to see at auditions. I was kind of from that few years older than the other group. So then Taps happens, and that becomes, there's these different movies in the early 80s where it's like these ensemble casts with all these people that the trajectory is headed a certain way and i think taps was probably the first one of those but then the outsiders happen and a whole bunch of them

well and to me what was significant about taps was really before taps it was that when i first started to become an actor i remember that you know you know, reading about Nick Nolte, who I think was about 39 years old when he played the high school kid Tommy Jordache in Rich Man, Poor Man. Oh, yeah. And was, I guess, the equivalent of James Dean to my generation of actor, you know, in that moment.

And when I read about him, and he was working steadily in the theater until he was in his late 30s, that was what I assumed would be the trajectory. Yeah. Because nobody of our age group, by ours I mean the group that I mentioned being kind of part of, there were no movies being made with leading young actors like that. And I don't think there really had been since James Dean. If you look at really what was going on in the culture, it was older. It was, it would have been like Richard Gere would have been the youngest kind of actor. And that's

significantly older in that, that relative to that age than I was. So you didn't look at it like, well, well, here comes my film career. You're going to work in the theater a long time. And that was great by me. And then Ordinary People happened. And that was Timothy Hutton. And him becoming a star is what got studios interested to make movies around him. And so that led to Taps. That led to, I think, this young generation of actors because he didn't only, you know, star in that movie, Ordinary People. He won the Academy Award for it. And all of a sudden, you had, you know, the movie people

taking seriously the possibility of younger actors again. And that started, and so I got in at a really lucky moment. You know, I think all of those of us that got to, you know, continue careers out of that time had a really lucky moment because two years before that, nobody was making movies we could have played leading roles in. Right. You didn't go for Ordinary People, did you? Oh, yeah. I climbed the fence at Warner Brothers

and snuck into Redford's office. Did you really? Yeah, because I had no agent. I wanted that like hell. Yeah, I read the book inside and out. Yeah, that among others. Yeah, I knew all the best spots in the studio, lots to climb the fence because I didn't have an agent. Sometimes people would kick you out, but a lot of times they'd sort of— Why didn't you have an agent?

You just couldn't get one. I couldn't get arrested. I was the worst auditioner in the world. I think I had a chip on my shoulder, too, about doing that. I was doing a lot of theater, and I would try to get people to come down and see me play a character rather than hold some sides and pretend I knew what the material was. So you climb the fence, and you head toward Redford's office.

What happens? I sit down on the couch in the outer office. There's a few other actors there who are there legitimately who have appointments. And just before I'm, the first person that noticed me sitting there was Robert Redford who walked by. And he said, hi hi how are you kind of looked at me and i thought you know in my mind it was that that's right that's right i'm the guy

you're supposed to cast yeah um but instead he was just very cordial and assuming i was among those on the list and by the time they got through the three actors that had appointments the casting directors um secretary uh realized that i might not be supposed to be there. And I think I was asked to, you know. How'd you get Taps? Because that was a big movie. Yeah. I kind of gave it up here in Los Angeles because I couldn't get represented. I had about $800 cash and bought a $100 plane ticket to New York

and put $300 down in a security deposit on an apartment. Not knowing what next would happen, I went with my high school buddy Joe Vitarelli, who later became a great film composer. And we went to New York together, got a place. And three days later, just as lucky as I could be, through a friend, got set up on an audition for the Lead in the Broadway play, and I got it. So I was in New York a whole three days before I got a Lead in the Broadway show,

a show called Heartland. And they were casting taps at that time, and the casting director was a diligent theatergoer, and she came and saw it and asked for me to come in and meet with uh the director harold becker and timothy hutton who at that point was cast and was uh i think had a little bit of a say in uh who he felt he would want to work with in it and uh we hit it off and uh that's how it happened it's funny it's funny you two and Cruise yeah in uh I mean that movie was almost 40 years

but and then Spicoli happens in Fast Times and I just know you as the Spicoli guy right and then when you

started being other women it's like oh look at Spicoli but I mean that movie was such an important influential early 80s teen movie

and it kind of predated what would happen with John Hughes and all those, you know. And then that character, people just loved it. It tapped into something. Yeah, which I think was really a tribute to Cameron Crowe and Amy Heckerling, Art Lentz and Don Phillips and those guys who really put that movie together.

Because for me, it was, you know, at that point, it just seemed normal that these movies were starting to happen. Yeah. You know, you didn't know if you were in something that was going to hit a common nerve, you know, whether it was a drama or a comedy. Or in that case, I was already in my early 20s. Yeah. And I had been alienated from high school when I was in high school. So I certainly couldn't have spoken with authority about anything that was going on culturally at any time in any high school. So I certainly wouldn't have known that we were, you know, hitting a button with a lot of people.

So then you get bad boys and then it really takes off because you're actually carrying bad boys. And I ride for bad boys to the death. It's such a good premise, and I'm always amazed people hadn't seen it. It's like these two guys end up in juvie together, and they hate each other, and they have a real ax to grind, and it's going to go down for an hour. It's just great.

Well, you know that you're getting to a certain age when they're making the sequel to a bad boys that already had been made that has nothing to do with the Bad Boys that you made 20 years earlier and 30 years earlier than whatever it is. But usually it goes badly because if there's two movies that have the same name and you love one, but the other's awful, and you get excited if you're flicking channels. But that one, I actually liked the other Bad Boys too. They went two for two with that one. Yeah, I didn't get to see. I think the sequel just came out.

Maybe I saw. Well, there's a third sequel coming out. Oh, it's the third. Yeah. So after Bad Boys, now you're in control. You get to start doing things you want to do. Then I was in a pretty unique position because based on the roles that I was able to get,

they turned out that people paid attention to at that time. They were very different. It was Spicoli. So I think that I benefited from a perception of a kind of diversity or an ability to, you know, do more than one thing. Is there competitiveness going on with all the young guys back then? Are you all measuring each other up? Everybody's getting these great roles, great movies.

Is it like sports almost? You're sizing each other up? Here's my answer to that question. I remember doing a movie where, I did this movie, Mystic River, that Clint Eastwood directed. I've heard of it. And the cast was pretty much people I had known or known of my entire acting career. Really?

Because we were, you know, Kevin Bacon and I had worked in the theater in New York together. And he was with your brother, too. And Kim Robbins and Marcia Gay Harden. They were all people that I either, you know, it was the timing was similar generation. And I remember recognizing now everybody had kids. They'd already established their career. They were, and there was no sense of competition. There was support.

And I remember the good feeling of that. When I go back and I think of the earlier times, I never did well with paying attention to competition. When I paid attention to competition playing tennis, I tensed up and lost. If I wasn't just dancing, it was no good. And so I didn't like sports for that reason. That's what led me out of sports. I loved the playing of them, but I hated the competition of them. And still today, it stresses me. Like, I'll love to watch, you know, Brady do something that is beyond imagination.

But the stress as it's about to happen dominates my experience. Well, that's why you like surfing. Yeah. Exactly, because that's just you dancing with a wave. Yeah. But what always gave me confidence and liberated me from ever feeling competitive is that it was never going to keep you from having a career if there were two, three guys in front of you who were at least as good, if not better than you.

What I was confident in is that I would go to the theater or I would go to the movies and it was never that I thought I was so good. I just thought I was better than them. Yeah. And I don't mean all of them, but enough of them that I'd have a career. Yeah. And that if I got a little better the next day, I'd be better than more of them, you know? And so it was a competition myself. And, and, and I, I look back on now, anything that I've ever done in my life where I invested in competition went wrong

and didn't feel good. What's an example'm i i'm gonna go to something too personal too fast let's come back to it no come on example i'm trying to think of a competition well i'll come back to it yeah you might have to because it gets coming it gets it goes well i remember falcon the snowman was ewan hutton and at that point hutton was still the golden boy won the oscar but he's got all these and that was basically you yeah you and Hutton. And at that point, Hutton was still the golden boy who won the Oscar. But he's got all these. And that was basically you and him leading that movie. But it was more my buddy Tim and his buddy Sean doing something that would not have even happened were it not for his involvement.

So I was just, you know, at that point I was seeing myself as kind of like, oh, I'll be that guy. I'll be like the, you know, I'll get a lot of great parts as the buddy and never have to carry the damn thing. Right, right, right. Sounds good to me. That one, I don't know how much of this was intentional, but at some point during the 80s, it became clear you were trying to have a career and try to do all these different types of parts. Because I think it could go one of two ways, especially with the young actor, where they're either just grabbing parts and trying to be the lead. You actually seem like you're more interested in,

oh, that character looks interesting in me. And you were putting together kind of this list of different types of people you could play. And I remember in that movie, I was like, wow, that's Sean Penn? What's going on? He's like a different guy in this one. I always like when actors do that.

I don't mean to kiss your ass, but I'm back. I appreciate it. I think, though, that if I were describing that, it would be a very nonlinear, because you couldn't assume to get offered exactly the thing that was of interest to you humanly at that moment each time you were going to get a good script or you were not going to get a good script but as you decided between

when i got in the luxury of being able to choose between things or to be able to do things and and especially not have to audition anymore which was for me as you know standard humiliation. When it became a career, in essence, was being offered to me, I think that you go in this nonlinear way, but once you choose something, it kind of sets the course for what you will or won't do in the next thing, because you're looking to tie a thread together so that as much as possible, it's like if your whole career were one movie telling all the stories of the things that you wanted to express through characters. It's like a book of short stories almost. Yeah, that's right, where you're looking for some kind of cohesion in the that ties them all together because you never did you know the superhero movie or the you know the movie that had a chance to become an action

franchise or you were just you never went down that road well i remember the an actor who i'm a huge fan of joel edgerton yeah he's good he he had a funny thing he said when he first came to los angeles he said i'm i'm just trying to get through this without putting the underwear on the outside of my pants. And I thought, well, that articulates kind of what I've been trying to do, too. It seemed like you had, just watching from afar that whole time, a really complicated relationship with fame, where you liked all the things that came with, all the parts you were able to do and all the different movies you were able to be in,

but you didn't want the other stuff. And the other stuff you're just dealing with, but you wished it hadn't been there. Well, I don't want to lead you into the section of our discussion that talks about the book, but this question leads me to it a little bit so we we know that there have been you know we we all have that moment where we're saying gosh it's just not

like the old days in some way something you know we look back with great nostalgia about periods in a way that we might not look back with great nostalgia, you know, on the period of the founding fathers, if our skin was a little darker and we had a family history we were aware of. Yeah. All of these kinds of things. And we're very quick to be in the culture of complaint in the times within which we live and not see the things that have improved. And it's a struggle. I mean, I have my big struggle with those things. I like the culture of complaint. That's a good, I'm going to borrow that.

But then when I look back, okay, I'm born in 1960, and I realized as I was writing these two books, and this character who was born at that time, too, that it it is a kind of epoch that is a is in its own way what I call the the first Bob Honey book, it was often considered absurdist fiction. And in a lot of ways, I went along with that. But, you know, absurdist fiction had been done and very well. I think this is ludicrous fiction. It's ludicrous usage of language. It's ludicrous politics and ludicrous cultural invasions of kind of this, like what I do consider a kind of disease of celebrity. And you can mark it from 1960 forward. It didn't start with the current administration where we were looking at things that were ludicrous. I don't mean to, you know, use that word glibly

because it also includes horrifying things. The Vietnam War, those who opposed the civil rights movement, all of the horrifying things that we've seen and all the horrifying things that have culminated in the moment we're at, which is, of course, peak evil is what's happening environmentally. Yeah. So we can talk about what everybody's doing now and what this, but it really becomes a kind of look in the age of ludicrous is kind of where I define myself. And as an actor, it took a long time to get to a place where I understood why I was making the choices, why I was diversifying the palette in the ways I was.

Yeah. Because you don't really know where things are going until, for me, it took a long time. I mean, it took, you know, what I would hope for someone to have occur in their early 30s, you know, a basic level of a matured sense of oneself and their surroundings. That took me well into my 50s. Hey, let's talk about stance.

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Yeah. And I think that I saw people working very hard to get my attention with their criticism. And I found it, you know, an avenue to giggle at. So you, I get it. I see where you're going with that. Do you think with the attention we have with celebrities which really

I mean it goes back to the freaking 1930s but the machine has really been in place starting late 70s the 80s it really took off and it's gone ever since

and we see over and over again with younger celebrities or child stars or people who become famous like in that 19 to 23 range and a lot of them have trouble handling it like why haven't we ever tried to fix this well there's because i probably i i don't want to get hung up on the part of it that is specifically celebrity but i i can say for

example i i just um the the lady to whom this this recent book is dedicated to and I just got back from Cuba. We went to Cuba last week for a few days. And you might be recognized there. They will value warmly what you do. But it is just part of the fabric of that nuance of the exchange and the meeting of two humans. And that passes rather quickly into their interest in what you like to eat as another person they want to be hospitable to. And into you asking questions about them and how many kids do you have. And it becomes just a kind of, you know, just real life conversation. You can, in a lot of parts of the world, particularly in parts of the world where the stakes are much higher for people.

Yeah. And where they have not had the choices that we've had, there's less indulgence in something like celebrity and much more enjoyment of it. There's not a kind of possessory feel that people have somebody or something or a particular hunger to be it. You know, there's not, you know, the Cuban culture, for better and worse, there's not a lot of upward mobility, whether you're, you know, famous for what you do or not famous for what you do. And so there's a kind of, you know, I think in the best part of that culture is the, you know, is the common nature of people. And there's a lot of warmth in that. Here around celebrity And there's a lot of warmth in that here around celebrity.

There's a lot of desperation. And when we're talking about Los Angeles or New York, there's, there's a lot of active desperation and envy. Yeah. And, um, and I think it creates a culture of a lot of self loathing.

And, and that's the, the, you know, that's the good news. It gets a lot worse from there and what it leads to finally is that when we take a poll

of who is the country's favorite celebrity, we will have been part of creating that which gets elected president. I figured you were ending on that one. part of creating that which gets elected president. I figured you were ending on that one. Your career, you go like 20 plus years, and then you win the Oscar for Mystic River, and then you win again a few years later for Milk.

I thought your attitude about winning the Oscar, it made me laugh. Like you didn't take it seriously. Because for most people, it's like, this is the exclamation point of my career. I've made it. And you just didn't see it that way. Well, I don't want to say I took it seriously or didn't take it seriously. What's very serious about it is that, you know, when you make a movie and movies wouldn't be made without uh you know let's say marketing departments without all of the other elements of getting a movie out there distributed and that's studio people yes it's publicists yes it's also your fellow actors kind of going out there on the hump you know the director the producers and a lot of effort is put in to movies

getting these nominations or getting these awards by a lot of people you care about yeah and when it's on you know part of it is on in support of you as part of that that movie the biggest reaction you can have if you win the damn thing is relief. It's like, okay, they didn't waste their time. They didn't, you know, everybody's happy. I can go home now. The, you know, I absolutely understand the excitement that people can have about all of that stuff. But I had remembered

and, you know, the Academy, I suppose, which I never, I don't think I'm even a member of the Academy. But, you know, so if people want to get mad at me, they can. But it is as true as not when somebody once said to a winner of the Academy Award, welcome to the club of mediocrity. Because so often that's the case. And then there are these years where I'm no different than anybody. I mean, for example, when what must have been a unanimous decision and Robert De Niro won for Raging Bull. It's a triumphant moment in the arts. Yeah.

But too often, you know, some bad, you know, when I say TV movie, I got to be careful because my reference is what TV used to yeah, wins best picture, or some saccharine wink at the audience performance, wins best performer, actress, or actor, you can't help but just turn on forensic files. Yeah. And decide to have a good time that night. What part, since you became a working actor, what part have you been the most jealous of that somebody else did we were like oh man what an awesome part i would have loved that one every part that ever happened under the direction of john cassavetes from before i wasn't oh wow

yeah that's your guy i think that you know, and I almost worked with John and got to be very friendly with him near the end of his life, and then he got too sick to make the film. But when I think about what would get me today excited about being an actor, it would be to work in movies with a director like that, taking on the subjects that he took on with the humor and the wildness of the true human soul

and all of it that was particularly unique to his movies. You've had some good ones, though. Early Fincher. 97. What was that? Tell me a Fincher story. Did you know?

Did you know this guy was going to be one of the guys? Because it hadn't totally happened when you were making the game of them. Well, David Fincher, who I cannot claim to know very well. I worked a short time with him and in a friendly way. Yeah. We never met up for a beer or anything like that.

And then I've run into David, you know, I mean, a handful of times since then, but I think his presence was one of somebody that was so in possession of his own imagination and the skill set to render it. Yeah. That he had a reputation that preceded his success. In other words, it was never going to be stopped. It wasn't like I look at him now as what he's become. He was that before he made a movie. So he's a very impressive guy.

A guy like Alejandro González Señorito, who I think is as great as any filmmaker that anybody's ever seen, you know, who's around, who I have. You know, I think when I was answering the question related to Johnny, it was about the roles. And when I think about the roles, I think about who was going to create something for their own surprise. And I was going to get to surprise myself within it. And if we surprised ourselves well, it was going to work. And if not, it would work on the next one.

Yeah. What did you learn from clint oh calm and i still haven't learned it well enough he uh he has he he is a guy who i think for whom filmmaking is such a effortless part of who he is. Yeah. And his jazz background, I think, is where I'd find it most clearly reflected because he's kind of famously ready to move on after one take. Right. I think he's a big believer in the magic of the first improvisation, in jazz, or the first take and what the actors do together and the first time.

He doesn't like to belabor things. And that's its own magic when it works. But you take that and you take somebody like Alejandro, well, for that magic, I mean, he's going to, he's going to, the only person he's going to torture more than he does you is himself. I mean, he will work as hard as, he will make sure he works harder than anybody else. Yeah. So you always feel in solidarity. Who would you rather work with out of those two styles?

What is more fun for you? Oh, that puts me in an awkward social. I don't want to answer. I would say that I was really... Depends on the person. I was very lucky to work with both of them. Yeah. Do you like being able to craft what your vision of the part is?

Or if you feel like the director has it and has had everything lined out, you're just going to trust him and do what he wants? Or does it depend on the movie? I think the second description is a description of a very bad director yeah um you have each person whether they become an actor or not has an actor inside yeah and there's a kind of music that you hear that that in your body that that takes you to a character you know at your best more fully than at other times that say and for a director

to assume that they know all the beats of that music and therefore decide which of those beats they want to use as their clay, is a misread. And everybody's music changes every year they live. Yeah. Which is why you'll see in some actors and actresses, big surprises very late in their career. Or you'll see something happen where somebody, you know, Gary Oldman's an interesting kind of tale of this.

Gary Oldman was, without a question, one of the actors of our young generation. And everyone knew it. And until he played Winston Churchill, just because of a variety of whatever was going on in his life, the choices he'd made, I'm going to guess that most younger audiences flat out were going to miss ever really knowing about,

not that he ever stopped working, but he was not doing uh darkest hours or something yeah and i remember being you know just i had never thought about in this way but when i saw him in darkest hours this kind of thrill comes in yourselves wait a minute, this generation gets to see the Beatles play. I thought that they weren't going to, or they never even heard of the Beatles. And so a director has to be aware of time and change, and what an actor is in their heart is kind of a searching thing, and they shouldn't be fully anticipated.

You never worked with Paul Thomas Anderson or Tarantino. No. Any reason? Well, Quentin asked me to do one movie at one time that it wasn't for me to do. It wasn't something that I wanted to do. What was the movie? It was one of the parts in Pulp Fiction. What? But, see, I wasn't upset that I wanted to do. What was the movie? It was one of the parts in Pulp Fiction. What?

But see, I wasn't upset that I had done it. I thought it was much more fulfilled by the person that did it. I don't want to say what part and get into those stories. Yeah, you got your whole action. I'm just going to think about it for the rest of my life. Paul and I talked about a couple of different things. And I remember he made that terrific movie with Adam Sandler. Yeah, Punch Drunk Love.

Yeah, and he came to me to talk to me about one of the parts, but it wasn't Adam Sandler's. I read that script. I said, sorry, I already fell in love. I fell in love with the part you've cast. Yeah. And, you know, let me know if Adam Sandler dies, and I'll show up.

That was basically. Well, he was tight with your brother too. Who's that? Paul. Yeah, yeah, yeah, yeah. They'd work together. He's in Boogie Nights. Nobody realizes he's the studio guy

with Dirk Diggler, yeah. He scored both Boogie Nights and Heart 8. Yeah. And then his wife, my sister-in-law scored Magnolia, yeah. Yeah, Amy Mann being your sister-in-law is an underrated random fact. She's a very talented woman, isn't she? Yeah. Yeah. Boston's own. talented woman, isn't she? Yeah.

Yeah. Boston's own. Yeah. We didn't talk about Nicholson. What'd you learn from him? You spent a whole, you directed him. You did a whole thing. You were with him every night.

I remember reading the stories back in the day, but you actually like kind of bonded with him. He's, you know this this figure of speech is overused and i think but when when one says they broke the mold yeah i'm gonna go on record there will never be another jack nicholson it's a fair one um because i believe that you, and this might sound like a flamboyant comment, I believe he has got the mind of James Joyce. I mean, he has a brilliant, again, I'll use that word linear, linear slash nonlinear thinker. Yeah. nonlinear thinker yeah wordsmith you know a great reader very very literate among the most caring people I've ever met certainly the most supportive and

most significantly supportive in terms of everything that I got to do with my career from the time I worked with him. Wow. He, you know, he's, again, an actor. There's no such thing as a better actor. And, you know, arguably among the great actors, he is, over and over again, is the most charismatic film presence we've ever seen. And as true a person as you'll ever run into. So whether you're talking professionally, creatively, humanly,

I can't call attention to all the things of him that I appreciate other than to say that I feel, you know, an awful lot of gratitude for having had him, you know, it's intimidating to direct somebody like that. He doesn't let that happen. Yeah. He is your soldier. Really? If you're a director,

he's the guy that's there to make you better. So what's going on with, you might be retired from movies, but now you're not, you came back. You're not done acting. Well, here's what I can tell you. Oh, that if it requires more than two days in a less than stellar location with a less than stellar paycheck and a less than stellar script and director, and you see me doing it,

you should assume I'm miserable. You know, the other way of saying that is if it were a couple of days on a great thing for a load of money in a great place with a great director, I'd love to do that. But stopping what feels like the movement of my life to do that for a living, I don't want to do anymore. I don't want to wake up, put somebody else's clothes on and dig up stuff from the inside of myself and do it according to a schedule.

I don't think that's what happens. I think you're getting your creative Jones from these books. No question about that. Ever since you started throwing yourself into your novelist career, all of a sudden you don't care about acting anymore. It's basically, I used to write columns forever, and now I love doing podcasts and I don't write anymore. It kind of shifted my brain to this different place,

and I wish I wrote, and I don't. But I'm just kind of over here now. And I don't know if I'm ever going to go back there. But I feel like maybe that's what's going on with you. Well, of course this will be misinterpreted as an absence of appreciation for the luck that I've had and what I've been able to do in film as an actor and what it's given me in terms of being able to make a really good living and being able to have a lot of freedom and all of those things. The part of it

that started to work negatively on me and started to be not enjoyable, I think it took it getting to the point where it was a prison that I had to break out of for me to do what I'd always wanted to do, which was write a novel. I was going to procrastinate my way into hard time and then write to break out of that prison. And I think that writing these books is a combination of that drive to be able to express myself freely without a studio, without anybody I was responsible to, because the greatest thing about writing a novel is that, yes, they can do well or not do well. So far, the first one did really well.

The second one's coming out. We'll see what happens. September 10th. Yeah. they can do well or not do well so far. The first one did really well. The second one's coming out. We'll see what happens. September 10th. Yeah. And, but by the time, you know, you call,

you cost nobody any money while you're writing. Nobody is taking a leap of faith in you. And sometimes not understanding what you're really trying to do. And therefore disappointed. Even when you feel you've succeeded in it. Like you can make a film and you described, they asked you if you really were going to make a bird and you said yes and they were looking for a swan

and you made a falcon or vice versa. You misunderstood each other. And so you disappoint people or you alienate people or this movie is too graphic or this movie is too and you just get censored and censored and censored and you bleed yourself over the money it costs and and the pressures that come on to you with a book by the time other people are investing in it they know exactly what they're investing in and they're all adults and so on you're not you've finished it yeah and then you say what do you think and if a publisher likes it they're all adults and so on you're not you've finished it yeah and then you say what do

you think and if a publisher likes it they're your partner and they'll be your partner in failure or success and nobody there was nobody felt misled and the liberation of that to not disappoint friends or get in you know get it or even have to consult and to and of all, to now be completely free of any self-censorship. Because you have to censor yourself as a screenwriter the moment you write a paragraph that's going to cost an extra $20 million because of what it's showing. Yeah. I can write this into a novel. It doesn't matter because it doesn't cost any more to have a bigger imagination.

I have two thoughts. First one is it sounds like when people retire in sports, a lot of times it's not because they're washed up. It's just the process of getting ready to play another season. That's what they get scared of like the summer knowing that oh shit now i gotta spend three yeah i'm both i'm washed up and terrified you're not washed up though no that but it's that off season freaks them out and it becomes such a big burden then they just don't want to go through it anymore that's one thing the other thing is i totally get what you're saying with the book i wrote a 700 page basketball book once and a lot of writing 270 000 words or something but um but you get in this mode where it's just you in the book and you're the only one who

understands it and you're trapped in it nobody can help you and i kind of liked it i'll never do it again because i i almost like went over the cliff with it. But I totally get like all I did every day was just think about this book. And I was the only one who knew where all the pieces went. Yeah, but you also had to get your facts straight, right? I did. I had to do everything. Yeah. I have no obligation to facts in my novels.

But when you're writing a novel, it all has to make sense in some way, right? You're the only one who knows all the jigsaw puzzle pieces. That's what I missed. Yeah, well, so much so for me that it actually is part of the fun, because it's the same for me in most conversations, where even with people who know me well, they will say, you know I had no idea what you were talking about. Right.

In most of the conversations that I have. And I've been accused of, you know, talking in riddles and so on. When I think that I'm being absolutely clear, when I write, I then, after I back off from what I write, I back off and I look at it, I go, nobody's going to understand this. And now I can see it. So it is true of me what they said. But now i can sit there and i've got i i don't have to think hard or let my mind be free to create what i want to create because it's created now i i'm going to juxtapose it now i'm going to clarify it you know so i kind of do two significant versions when I write a book. I say, like, I've written so many books. Now my second book.

But in both cases, one version that's mine. And the other version is all the same writing, but I've taken lines from here and put them over here. I've put a period here. And it's just putting it in an order that allows someone else in. And these still challenge that. And I like that. I like it that way, but I do make sure that by the end, I, I let some trusted people read it without telling them what to expect. And if they can tell me that they read what I intended and they tell me about, okay, I say, what's it, what is the book?

And I hear back and I know it can be understood. That's enough for me. I still think from a career standpoint, you need your equivalent of the verdict. Well, that was my equivalent of the verdict. Well, here's the funny thing. I remember that being like the older, like the elder Paul Newman. It wasn't even elder. It was just older.

What I was going to say is I remember it that way because of the age I was when I saw it. Yeah. He might have been younger than I am now when he did it. And so when I think of that, I still have the old perception, which means like you're talking about something 20 years from now. And that's how. I think what was so key about when he did that was he was finally saying like,

I'm in a different point in my life and I wouldn't have played this part five years ago. But now I'm just old enough that I can play this part and it was like a different side end. He should have won the Oscar. Yeah. And also again, a wonderful script and a great director.

That's a good one. Sidney Lumet. So you're surfing, you're writing books. Not surfing enough, but I'm writing books. How old are your kids now? My son's 26 and my daughter's 28. How's that going? It's going great.

FaceTime? Do they FaceTime you? Well, I see them quite a bit. In fact, I just directed both of them in a movie. So that's the last. I did that right after I finished the book. Are your kids more like you or their mom? Well, what I like to say is they got my looks because their mother kept hers so uh but uh they um but i got two beautiful talented smart children um and they've got pieces of both of us in them

and uh and and i yeah and so i just how do you think they describe you but you gotta pick their friends depends on the day depends on the day fucking dad Jesus yeah yeah well good luck with this book

it is called Bob Honey Sings Jimmy Crack Corn comes out on September 10th how much how many shows are you doing

you're David Spade I'm gonna go do David Spade's show put a tattoo on him he still has the other one I'm doing it I am he showed me it he still has it I just gave the kit one. I'm doing it. I am. He showed me it.

He still has it. I just gave the kit back for them to take it over. It's such a great story. Yeah. I'm going to, you know, he knew I had a tattoo parlor

before I did that, which I called Sean's OK Tattoos. And it was because they were just OK. And I'm out of practice, so I'm going to go do a less than OK tattoo

on him right now. All right. And we welcome you on the Patriots bandwagon. I know you like championship winners. Thank you. Thanks, Sean Penn. Thank you.

All right. Thanks to Sean Penn. Thanks to Jacko. Thanks to ZipRecruiter. Don't forget to go to ziprecruiter.com slash BS. And thanks to Spotify. Don't forget the hottest take premiering next week exclusively on Spotify. You can follow that feed right now.

And as soon as we start dropping them, you'll have them. Back on Thursday with Million Dollar Picks and Mallory's Most Intriguing and a whole bunch of other things. We'll see you then. I don't have.