The Bill Simmons Podcast - Matt Damon on 'Good Will Hunting,' 'Rounders' and Breaking Into '90s Hollywood | The Bill Simmons Podcast (Ep. 423)

Episode Date: October 3, 2018

HBO and The Ringer's Bill Simmons is joined by Matt Damon to discuss his journey through Hollywood with Ben Affleck, 'Rounders,' 'Goodwill Hunting,' the 1990s class of actors, baseball, and more. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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Oh, yeah. Use promo code BS, download the SeatGeek app, or go right to SeatGeek.com. We are brought to you by TheRinger.com, where we had an awesome oral history about rounders two weeks ago. We're going to be talking with Matt Damon about rounders in a little bit. The Rewatchables, check out that podcast. Dazed and Confused went up this week, the 25th anniversary.

That's happening. Also on the Ringer Podcast Network, our new podcast with Ryan Rosillo, Dual Threat. That's happening, the Ringer NFL show. Channel 33, where you can find a whole bunch of pop culture smart talk about the media politics all kinds of things check that out check out everything we have at the ringer podcast network coming up a podcast i taped with matt damon a couple weeks ago actually we were doing the oral history for Rounders. I did the interview for that. That was the impetus, went over to his house and decided to make it a deep dive about

what it was like to be an actor in the nineties as Matt Damon, all the people that he, you know, were in basically his class, which we're going to talk about and all the things that happened to them, all the jobs that they were going for in the 90s, and eventually how his career exploded with Good Will Hunting right before Rounders came out. So we talked about that and a whole bunch of other things. We did this before he went on Saturday Night Live to do the bit about Judge Kavanaugh. So that was before this. That's why we didn't talk about this.

But this was a good one. And thanks to Matt for all the time. This was a great one. I was really psyched about this one. It's coming up right now. First, Pearl Jam. All right, we're here at Matt Damon's house. We were taping this for the Rounders' 20th anniversary of oral history that The Ringer is doing.

But now we might just open it up a little bit into like a 90s movie podcast because I think the way your career was going leading to Rounders I think is interesting too. But I was going leading to rounders I think is interesting too but I noticed your Jim Rice jersey I feel very comfortable here yes you're you're safe yeah friends yeah I was a Fred Lynn guy but I liked all I was a Fred Lynn guy too I mean that whole outfield I mean Evans Lynn and Rice and then Yastrzemski of course that was those were my guys um I did when in 99 at the the all-Star game when they played it at Fenway, I did the celebrity hitting challenge and was on a home run,

you know, a celebrity team with Jim Rice. Oh, really? Yeah. Was he a nice team? Oh, he was great. He was great. I mean, he was known as kind of being ornery. Yeah.

That was always his reputation, but he was super nice and was still belting home runs. Right. I mean, in 99. So he was probably, gosh, what he would have been, 50s or 40s? No, I guess. Yeah, like late 40s, early 50s. Late 40s, early 50s.

I guess. So I'm 47. So I guess it's not that surprising. You have warning track power now? You know, in fact, back then, we got the night before the All-Star game. The old greensman there used to do it 20 years ago. Joe Moody was his name. Yeah.

And he led us on the field. And I got to go on the field with my dad and with my brother and with a few, like a handful of friends. And we had batting practice from midnight to one in the morning. And it was, it was. They put the lights on for you? They put, they had the lights on because they were, they were literally, they were literally drawn, putting the lines down for the game. And, and I hit the wall. My dad was a pitcher in college and, and I hit the wall, you know, wood bat off my dad.

And that was it. and I hit the wall, you know, wood bat off my dad. And that was it. It was like with the joke that night, we were driving out of there and we were like, I said, I'm never going to need therapy. Because like that just happened. And we were saying we should just jump off the Prue. Like that's it.

We peaked. We've all peaked. It was the most awesome. Sean McDonough was there. Sean was one of the people with us. And there was like a handful of people. It was just this unbelievable moment. What happened on the Oprah show when you got a pay-to-release jersey? Yeah, I went on the show. And that was after that 99 season when he had just the greatest, you know, one of the greatest seasons ever for a pitcher. And out of nowhere, I mean, Oprah being Oprah, you know, I mean, people get cars on that show sometimes.

You know, I mean, and she's, I have a gift for you. And I was like, oh, cool. You know, I didn't. And I opened this thing and it was Pedro's. He had four jerseys. He had two home and two away. And it was one of his travel jerseys for that year oh my god so that so it had the little tag on it it's got it's the it's his

thing and he and he and he signed it to me and uh so that was you know in in terms of like my life being becoming totally surreal 20 years ago around the time of rounders so it's like oscars you hit a double off the wall on Fenway and Pedro gave you a Jersey. Yeah. Like a two year span. Yes. Yeah. Yeah.

Yeah. It's amazing. You're still here. And then I, and I realized then that I lived inside the matrix. Well, let's go backwards. Cause we want to get to the rounder stuff,

but you for years and years, you had, it's interesting. We talked about this. We did a rewatchables podcast about rounders that we haven't run yet. But we were talking about how you're part of this era of 90s actors.

Like when we were growing up, we always heard about the guys from The Godfather. Right. And, oh, they idolized Brando, but then this whole new class came out and it was those guys and then De Niro. Your era never is considered to be an era, but it really kind of was an era.

And I remember you telling me there was this whole stretch where you guys were all going for the same movies and they were all people that became pretty famous. Yeah. I mean, out here in the early 90s, there was a handful of, you know, in terms of leading men that I would go up against. You know, I mean, it was a lot of the guys in School Ties, you know, the terms of leading men that, you know, that I would go up against, you know, I mean, it was, it was a lot of the guys in school ties, you know, the movie that we did and the guys in days. Stop it. I love how you pretend I'm not aware of school ties.

No, but I mean, you know, it's not, it wasn't a big hit movie. It's not like days and confused, which although it wasn't a huge hit, it was, it's really a big ensemble young cast. Yeah. And so if you looked around all those actors who were kind of in that in those in those movies that were around then were pretty much the people that that would you'd see you know you'd you'd go in you'd get called back you'd get called back again it would get whittled down and you'd see like you know ben or or mcconaughey or or you know you'd hear ed was leo in this whole world no leo was already a star yeah it was already like you know because you'd hear Ed Norton. Was Leo in this whole world? No, Leo was already a star. Leo was already like, you know, cause he kind of blew up with this boy's life when he was probably 13 or 14.

And then he did Gilbert Grape. So Leo wasn't auditioning for him. That was it. He was just snapping his fingers. Yeah, no, like I auditioned for the Basketball Diaries. It was like, Leo's doing the Basketball Diaries. There's another part. Do you want to audition for it?

You know what I mean? So that, so he wasn't, he was already, and he's a little younger than us too yeah um so you had i think he's probably i i want to say he's probably five years younger than than our then you know if you look at ben and me and mcconaughey and uh is brad pitt in there brad's older than us and brad was also massively famous i mean thelma and Louise was what, 91 or 92? Oh, that's right. Yeah, yeah, yeah. So it already happened. I remember working with him. There was something on Oceans that George wanted us to do.

I forget what it was. It was some appearance or something. And Brad said no. And George looked at me and goes, well, look. He goes, you can't really blame the guy i mean he's brad pitt and he's been brad pitt a lot longer than we've been us like even the like even then i mean george kind of subsequently just become this kind of international icon but you know around oceans we were he was you know he was transitioning off of er he was and pitt was just i mean i remember

the first time we went to europe on that movie for to promote and george just tells the story of people like stepping over our faces in order to get to brett like they you know we were completely invisible we used to send him out like before us because there would be like a thousand people outside the hotel and we just said just Brad, just walk out to the left. And they would go completely bananas. And George and I would just walk out to the right and just go to dinner. It's no problem.

But like- George is in that class, right? He is now. He is now. But he was, you know- He's toiling away doing his own thing, trying to get seen. Yeah, well, he was doing, you know,

he was still locked onto his er contract yeah so i'm talking early 90s though he was doing like tv pilots all that shit oh early 90s yeah er was like 94 yeah 94 yeah yeah so yeah no he was he was ben met him at a barbecue i remember he came back i met this really cool guy he said he's he's done 10 pilots that have gotten picked up and none of them. None of them made it. And they all got made and then they all either, you know, like they were on for two episodes or eight, you know, and then just got canceled. Did you have one of those or you just were movies, movies from the get go? No, it was always movies.

Yeah. Why was that? Well, TV was different then. You know, TV was, I i mean it was a sitcom which i wasn't interested in doing yeah or it was a procedural usually you know like an hour long you know which which can start a lot young lawyer with a danger streak yes exactly and and like can't settle that ben's ex-wife jennifer garner okay so she was on one alias, you know, it starts out, everyone's like, this is really cool. And she, she used to make me laugh because she'd go by the seventh season or whatever.

It's like, there's aliens coming down. There's, you know, they're just, it just gets progressively more absurd, you know, and, and you're pregnant with the alien's baby and it's give me back my baby. And it's just, you know, and everyone kind of knows it's like, we're just running it into the ground. You know, there's just, you know, and everyone kind of knows it's like, we're just running it into the ground. You know, there are still people watching and, and,

and so. Clooney played it the best way I think out of anyone. But he did that ER and he got out as fast as possible. When he, which is five years. Yeah. And, and they were begging him to renegotiate.

And I think, you know, he was making like 30, 25 or 30 grand a week, which is obviously a lot of money. But to put perspective on that, the show was so successful. I mean, people were making hundreds of millions, like the people who created that show. I mean, forget it was just this juggernaut.

It was, it was everybody in America. There were four channels and everybody was watching ER. And George's last episode, you know, I think Anthony Edwards was making a million dollars a week and they had their last scene together and they'd started out together. But Anthony was like, you know, I'm gonna start on ER. I'm doing it. And they paid him what he was worth, right?

And they would say, George, just renegotiate. You're gonna make so much money. He'd go, no, I want to make movies. And that's what it was worth to him. So he never complained about it he just did his job and he played out his contract and and did what he wanted to do what was your first big break it's tough it's depends on how you define because there's there's so many of them that you know I mean because I just felt like school ties put you

on the map at least for me I'm like who's that guy man is he evil yeah yeah I mean, cause I just felt like school ties put you on the map, at least for me. I'm like, who's that guy, man, is he evil? Yeah. Yeah. I can't believe how he's treating Brandon Frazier.

This is totally uncalled for. No, he's a horrible character. He's really one of the worst characters of all time. Yeah. One of the worst that I ever got to play. Anti-Semite all-star. Yeah.

No, but not an all-star like a, or an anti-all-star. Yeah. Yeah. Yeah. That guy was not a nice guy. No, not a nice guy, but a nice guy but it was gonna he made it clear he's gonna turn out well for him no he knew it he knew the deck was totally stacked it's like he was the embodiment of like like pure white privilege yeah you know it actually is a really good movie that holds up

from a cable i haven't seen it in a really long time but that was a huge break for me and it was a big break because Stanley Jaffe, who was originally directing it, and Sherry Lansing were producing. Now, they had done Kramer vs. Kramer. Yeah. They had also quite famously done Taps. And so they were-

Another one of those young ensemble movies. So they were known as people who really had the eye to, and so to kind of be cast um by them because stanley was originally the director of the movie um was a kind of a signal effect you know people went oh these are young act these are serious young actors i guess um and ben and i both got put in that movie so it was a it was a that was a big that was a big break but then I went back to college and the phone didn't ring. And I'd subsequently learn a lot about marketing and how to market. And they marketed it the way they should have, which was around Brandon because he was the star.

And he went off and did Encino Man after. It was like, OK, this guy's got another movie. He's the star of the movie. We got to blow him up. And then Chris O'Donnell got Scent of a Woman. You auditioned for that one, right? Everyone auditioned for that one. Yeah, everyone auditioned for that.

It's a great part. It was one of those parts. It was like, oh my God, opposite Al Pacino. And Chris went in and won it. And so everyone knew that movie was going to be big. And so it was like the marketing kind of emphasis went to those guys. And I it was like the marketing kind of emphasis went to those guys. And I remember being really hurt by that.

Like, like personally feeling like, well, but I'm, but I, you know, I'm nothing like this person that I'm playing in this movie. I'm really good in this movie.

Like, why isn't, you know, and I just, so you think they actually, that they held that role against you a tiny bit. It's possible. No, no, no. I don't think the whole role got held against me against you a tiny bit it's possible no no no i don't think the whole role got held against me i think i think it was just i wasn't talking i

wasn't talked about like those guys were talked about like i remember my brother going dude i saw this thing and it was like you know they were talking about the two actors who are really going to come off of this movie and they said it's brendan and chris and it was because they had work lined up. And I was back in school and I didn't have any other job. But I remember feeling like, well, and then that, you know, at any rate, that, you know, so, but it was still a huge break. The idea that I'd been cast in a feature film.

Some say it's the best naked shower fight scene ever. It's up there, dude. It's up there. Fil. It's up there. Filming that for five days. Yeah. Yeah. Yeah. My God.

My God. There's, I think there's probably a lot that was cut out of that too. I mean, it was just, yeah. So you knew Affleck,

you knew Affleck before that movie. Oh yeah. Yeah. We grew up, yeah, we grew up, you know, I mean,

he's up the street now and he's still a lot further away than he was 30 years ago. Yeah. And we were like two tiny blocks away. So you both get that movie. And now are you auditioning against each other for parts? Is it like competitive? How does that work? I mean, technically, I guess, but it was, you know, we were roommates. So it was like,

I hope one of us gets it because, you know, there was, you know, there's a, like when I got Geronimo, that movie with Walter Hill that, that, I mean, that paid our rent for a long time. He got this show against the grain, which was actually based on Friday night lights. So yeah. So it was the first iteration of a show. Yeah. So it's, it was, it iteration of i think this is on youtube yeah yeah so it's it was it was a friday night like on one of the major networks which was their kind of family night yeah programming right because that's who's home watching tv and so it was a real family it was real all shucks like you know little davies you know it was like it was one of those real kind of family shows it lasted like eight eight episodes, but it paid our rent.

Where are you living? We were in Eagle Rock at that point. Eagle Rock? Oh, you were way ahead of the curve. We were, yeah, a little too far ahead of the curve. I mean, if you have an audition in Santa Monica on a Friday and you live in Eagle Rock, then fuck, man. It's an hour and a half, kiddo. Oh, it's more than that. I mean, it's an hour and a half. Oh,

it's more than that. I mean, it's every bit of two hours, like each way. You and Affleck, is it, is it, what's the apartment? How big is it? Eagle Rock. Oh, there were so many of them. Oh, Eagle Rock was. Like one bedroom? Well, the first one, yeah, he was in college. He was at Occidental. So yeah, the first one was pretty shitty. And then, what did I do? I got Geronimo and then we got this place. So we had a little money and this place, we called it the castle. It was just kind of weird, dilapidated kind of architectural mistake. And it was me and ben and casey had just graduated high school and he and his other and a friend of his uh moved out to do a gap year and and casey was

going to audition and so they live they so it was four of us living in this in this in this kind of weird place in eagle rock and then ben at that point had already dropped out of school so it was like why are we in eagle rock yeah um but anyway and then you ended up in la uh and you're in the circuit then we ended up no then we yeah then we went then we the next instead of re-upping our lease there we i got a place with another high school friend in west hollywood ben got engaged to this girl and moved in with her and so it was that moment where we're like dude we're gonna sign this lease like and he's like no i'm getting married and we're like you don't seem too excited about it you know really and he was like yeah no no i'm getting we're happy it's gonna be

great we're happy and i'm like okay he was like 22 you're thinking intervention well no i mean it's not your play you know what i mean it's like what do you say you know he what are you gonna say you go like well the problem is are you sure like that's what are you sure because because seriously we're signing a lease yeah like we need a place to live and we gotta get it we're getting a two-bedroom or a three-bedroom so you tell us are we getting a two-bedroom or three-bedroom he's like get a two-bedroom you're like okay so me and our friend Soren, who we grew up with, Soren and I got this two bedroom on Curson off of Melrose.

And about two months later, Ben showed up with all his shit. And we had the only, you know, those little, you know, places on that street. You know, they're great if two people are living there because, you know, you got a little front room, a little living area and then kitchen and then bedroom, bedroom. Right. So Ben showed up there. You know, Ben's a big guy. Like there's no there's nowhere to put him. Right.

Yeah. And he had all his stuff. So now all his stuff took up our living room and he was trying to sleep on this couch like we had this couch this one of those black pleather couches from ikea that like you know that if that if you if you're one degree warm like you just stick to it and it's like and ben ended up um on that couch which which, which Ben's six, four, the couch was probably five, nine. Oh man. So we go in in the morning and his legs would be hanging off the end. And that was, I think, one of the reasons we, cause we were already writing Good Will Hunting, but we, we finished it

in that bungalow kind of apartment in, in West Hollywood, because we were like, this is untenable. Yeah. So we're going to work like, we have nothing to do. We don't have jobs. We have enough money that our rent is covered, but we're not going to make it through the lease. So we probably were writing 12 hours, 16 hours a day, and we had nothing else going on. And Good Will Hunting, the original movie,

had this whole second act where he becomes like, what's he in, the CIA? Yeah, it was the FBI. It turns into a thriller? Well, one of our favorite movies all time was Midnight Run. Yeah. So it was very much written by two, but like, you know, I was 22 and Ben was 20

when we started that. And we sold that version of it. And I was 24 and Ben was 22. So it was like a movie, an homage to Midnight Run written by these guys from Boston. And it was kind of a hot mess. Yeah. But there were some scenes in it that were really good and it was Castle Rock who bought it. And, and, and Rob Reiner, I'll never forget Rob Reiner in a meeting you know basically gave us permission to remove all of that high concept stuff and it was the high concept stuff that kind of sold it because people were like oh I can see how this movie will make money yeah and Rob was like we don't believe that

here like I there's something else here if you guys just want to explore these relationships you know um write the movie that you want to write and we're like oh okay well we'll write this then and uh and you guys were always okay with you being the lead and him being the sidekick yeah i mean i'd started it in college in a playwriting class and so it was all established by the time you know that was my final paper was this, I was supposed to write a one-act play. Yeah. And it was a, it was, instead I handed in the first act of a movie. And I said to the professor, I think I failed your class because this is not what you asked for, but this is what came out. And I really like it. And he gave me an A in the class and he said, yeah, it was

really cool because I didn't get a lot of straight A's at Harvard, you know, and he went, you know, no, he said, whatever, wherever this goes, he he goes I don't know where it's going but stay with it yeah and he was it was really great because I didn't think of myself as a writer I was an actor and and neither did Ben for that matter and so that was in late January and then in uh March I came out here for uh for spring break to audition for stuff and stayed on Ben's couch and showed it to him. Was like, Hey, I wrote this thing. I don't know what the fuck to do with it. And Ben read it and goes, I don't know what to do with it either, but we should do it together. And I was like, sold, I'm in. And so that was really the, the i i trusted no one in my life more than him yeah you know i

and we were just you know as he was as close a friend as i'd ever had in my life or ever could imagine having having and and i respected him and i and i respected his taste i mean we our taste kind of formed together you know what i mean that Those kind of teenage years where you're kind of spreading your wings and gaining your own independence. And we did that together, right? And so I know he would read a situation the same way I would. You know what I mean? We were just very compatible in that way.

Well, the movie then goes to developmental hell for like i mean almost two years yeah but to be fair it it it it got a lot out of that process there was a point at the end where it stagnated with castle rock yeah but leading up to that point the movie vastly improved because they allowed us to do you know to make to make the movie that we wanted to make to make it smaller um and uh and and yeah i mean it wouldn't have existed the way it did at what point was it like we're only doing this movie if we're in it where you hit hit that kind of game of chicken? Yeah.

Wasn't there when the new studio came in, didn't they tell you like, all right, we'll buy it, but you guys really got it? Everyone said they'd buy it without us. Everyone said, you will get so much more money if you just let us do this with Brad and Leo. Yeah. You know, and we were like, no. And they would all say there's no precedent for that. And then we would always say Sylvester Stallone. I was going to, those are the only two examples I can think of though.

Well, I think Chaz Palminteri did it with the Bronx Tale to a certain degree. Oh, that's a good one. Yeah. But he had De Niro. I mean, De Niro had seen him do the one act play. And so I'm sure Bob was running interference for him, just saying like, no, he's playing that part, period. You know what I mean?

But Stallone did it on his own stallone just refused and he he was flat broke with like a kid on the way and yeah they wanted ryan o'neill to do it i guess and yeah they offered him like an extra 30 grand or something and he just said no but you had gotten a couple other movies even before this movie got going right when yeah before you started filming you you lost all the weight for Courage Under Fire. Yeah. That seemed kind of crazy in retrospect. How many pounds did you get down to?

I got down to 139. Which was like legitimately unhealthy. Yeah. Oh yeah. For me. Yeah. I mean, I'm in shape now at 183. 139 is ridiculous.

Yeah. Yeah. I mean, it was horrible. They didn't tell you to do that right you know i just did it because i the guy was supposed to be recovering heroin addict and or not recovering actually he's supposed to be a heroin addict and uh and um and he was supposed to and and and there was this whole thing in that movie where there was flashbacks and i wanted to just make a strong physical delineation between what he looked like now and what he looked like in was flashbacks and I wanted to just make a strong physical delineation between what he looked like now and what he looked like in the flashbacks that that something had happened

right there's this incident that the whole movie's about like what really happened and it's kind of got this it's actually a good movie I think so I haven't seen it in a long time but but it was supposed to have this kind of Rashomon quality where you have different characters telling the same story and you see different versions of this story and you're like wow what really happened but when it got to me i wanted people to go like something is really fucked up something fucked this guy up and and there's and so i had the idea to lose a bunch of weight and uh now they would just cgi you uh god well they would have to because i would never do that again i mean it was just it was so existentially, you know. It seems like every A-list actor has to do that once where they just either lose a ton of weight

or gained a ton of weight. Maybe. For a role. It's like, you just almost had, it's like a rite of passage. Yeah. I mean, I do the CGI now. So that happened, but I was living in Charlestown when you guys actually got greenlit to make Good Will Hunting. And I remember the improper Bostonian that had you guys on the cover. And it was in this coffee shop that I always went to. And it was like, look at these young Boston kids making good, they're making their own movie. And I remember flipping through it and being like, oh, the guy from School Ties. Yeah, we had worked I mean you have yeah that's a pretty

deep knowledge then because most people like when Good Will Hunting came out people were like oh you're an overnight success no and we were like no you've been in a bunch of stuff

I was in the union when I was 16 like I'm not you know and Dazed and Confused Afa could have been in some stuff too but Dazed and Confused like O'Bannon

was like a real breakout character people knew him from that and then Kevin Smith yes and Kevin Smith was a huge part of getting us to miramax and chate was chasing amy that was before good morning that was before so ben was that was an intense movie yeah yeah and ben was like the the kind of indie darling yeah and then he kind of flipped from the indie darling to goodwill hunting came out and then he was in armageddon and everyone's like oh he's a, he's a big popcorn movie star.

Yeah. I remember reading it. I'll never forget reading that thing. And for some reason, it just stuck with me. Like, oh, that looks interesting. But never thinking it would be what it became. Right. And then you had like this whole, it was in the height of the whole people like leaking stuff, trying to undermine the Oscar campaigns of other movies and stuff.

You had to deal with this whole thing about you didn't really write the movie. Yeah, that was. Which was ridiculous. Well, that was the thing. We were like, well, you have like the hard drive. Like we have, we wrote, not only did we write the movie, we wrote a thousand fucking drafts of this thing. You know what I mean? Like that everybody's read read but it wasn't

that was a kind of a kind of a interesting wake up to the kind of the politics of award campaigns which have only gotten more insane but but that that somebody would put that out there and it wasn't meant to be a a story that anybody believed it was meant to be a story that came out timed perfectly. So at the moment somebody was writing in a name on their ballot, they'd go, huh, maybe I shouldn't write that. Maybe I'll write the other one. And that's all. It's just, I just want you to just change what, don't write Good Will Hunting, write this movie instead. That's all it was. And I remember actually Ted Talley, who's a great writer, he wrote silence of the lambs and ted talley was one of the people who said they said wrote somebody said wrote the movie and i subsequently

worked with him on all the pretty horses years later but i did never met him and he did an interview he called variety and said um you know it's being reported that I actually wrote this movie and gave it to these guys and he goes I just want to say for the record that I wish I wrote this movie and he just did this really you know and it just he didn't have to do that you know what I mean it was very just I remember feeling like wow that's

he's a big heavy hitter in this business and he just really did us a solid and kind of put that one to bed but and then you had you got the rainmaker before goodwill hunting right that's what got it green lit yeah so i was so so we had been at miramax in development for a year yeah and uh and gus had fallen out of negotiations because he wanted final cut and harvey wouldn't give him final cut and uh then i got the, I'm trying to think,

the deal fell apart and then they were, Harvey was trying to find other directors and there was a great Sidney Lumet story because Sidney Lumet, I think, was 72 at the time. Oh, wow. Read the script. One of the greats. Yeah, yeah.

And so when the Gus thing was ended, they said, how about Sidney Lumet? And we said, are you kidding me? Like we'd- The verdict? Yeah, of course. And we'd read his book, obviously making movies. And Sidney read the script.

The word that came back was once he found out he couldn't have final cut, he said, I love this movie and I'd like to direct it. And he said to Harvey Weinstein, he said, with all due respect, I wouldn't direct this movie with your dick without final cut. He said, I love this movie and I'd like to direct it. And he said to Harvey Weinstein, he said, with all due respect, I wouldn't direct this movie with your dick without final cut. And that was it. And that was it. That was just over. We were like, that's what Sidney Lumet said to Harvey Weinstein. Like, that's amazing. Quick break to talk about Casper Mattress. Casper is a sleep brand that continues to revolutionize its line of products to create an exceptionally comfortable sleep experience

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because that was the first time I met Edward Norton. Yeah. So, so Edward, so Primal Fear was a movie that came around and was this unbelievable role. We were like, it was like Scent of a Woman. We were like, this is going to blow up an actor. I remember I hired a dialect coach that I couldn't even afford to get to prep for that audition.

Really? Yeah. I mean, it was a big one. It was like, this is, you know, you're done if you get this. And it was actually one of the things that helped me understand. And Ben and I had a real come to Jesus meeting about it, I remember, because when we both got close and didn't get it. And this guy named Edward Norton got it. that a movie with a role that's great for one of us is going to make it all the way through the ranks of established actors who are all going to have to pass on it. And then it's going to get thrown out into the kind of, into the, into the open here with, into this jungle with all of us.

And the thousand of us are going to go for it. Like, what are the odds that you're actually going to get one of these parts? It's going to change your life. And we were like, fuck this. We got to write this thing. We have to write it. Yeah. You know, that you're actually going to get one of these parts that's going to change your life and we're like fuck this we got to write this thing we have to write it yeah you know because it's never going to happen it's never going to happen if you wait for it and yeah there are the people who do it and it happened but it's like if that's your strategy it's not you know what i mean it's such a hail mary so you had like school ties brandon frazier senate woman chris o'donnell um primal phil ed norton so there's three parts in six years yeah that transformed somebody yeah i mean there was there were other ones that came along like powder people

thought were going to be it was going to be a big i remember that you know i got close on that one i i can't remember there were a bunch of movies i was you know it was the same group of people around a lot of them um and uh and so at any rate so when the Rainmaker came along the Rainmaker was interesting because I got a phone call I'd been tracking it and tracking it because I knew Coppola was doing it and that was obviously my guy, the godfather and it's like all of these actors

and he was legendary for how he worked with actors and Patrick called me and he said okay because we couldn't get an answer from them. We couldn't get an answer about where I should go and when. And Patrick finally called and said, listen, he's screen testing people in Memphis. You're not going to get it.

He said, I put your chances at 5%. Edward Norton's going down there. Uh-oh. And I'm like, fuck. Let's get him. Because Edward's not only done Pr there. Uh-oh. And I'm like, fuck. Let's get him. Because Edward's not only done Primal Fear at that point, he's done Milos Forman's movie, right? Yeah.

People vs. Larry Flynn, and everyone's saying he's fucking amazing in it, right? So he goes, but there are three actresses that they're reading, and they only have two actors, Edward being one of them. Patrick's like, it's a Hail Mary. And I'm, he's like, will you go get, will you go to Logan airport right now? And I was like, yeah. And so I flew to Memphis and that next day screen tested for Coppola. And that night, Edward and I went out and, um, and hung out, you know, we had like a night on Beale street together. Yeah. And, uh, and cause I just, you know, I mean, he was a guy, he's my age, incredible actor, like this guy that I just really admired. And, and I remember that night just

saying to him like, well, I mean, it's really fucking cool meeting you, man. Like, have fun making the movie. Like, I really thought, you know, it's done. And then over the next, it took like two agonizing weeks where they went back and forth between us. Like, it's looking good. It's not looking good. It's looking good. And then I got the call that I got it.

And then that was the most. How much money was that one how much money yeah I know you remember did I make six hundred thousand dollars which was I would bet I bet if we went through your IMDB you could remember the price of most of them the early ones definitely yeah yeah like like that one because the most six hundred thousand is a lot it's a fortune it's a fortune but but but I was I was the lead of the movie. It was like a hundred and something day shoot. I mean, this was a long, long, long movie.

In Memphis? In Memphis, yeah. And then San Francisco at the end, we did the stage stuff up in San Francisco. But the most I'd ever been paid for, I mean, I'd been paid a hundred grand for uh courage under fire yeah and uh goodwill hunting had not been made but ben and i had sold the script for 600 grand which we split nice and then i had a deal for goodwill hunting if it went that i get 350 grand um did you guys get points with

that movie or no no no no But you made up for it later. Yes, yeah. It completely, well, Robin, who's actually who did, you know, Robin made this incredible deal where he, where he, if the movie made over $60 million, he started to get some kind of escalating participation. And it was like, he read it and he's like, he just got it. And everyone was like, oh, this is cool.

We're getting Robin Williams cheap because he was the biggest movie star in the world. And I think he got $20 million a movie. And I think they paid him like five, right? And so they were like, well, great. Well, we're winning here. And then it just turned out Robin just- He had the last laugh.

Robin crushed him. So we never begrudged him that because that also gets a movie made. So you finished Rainmaker and then you knew you were doing Good Will Hunting right after that. Yes, because when I got the part, I sent a fax to Miramax.

And I think I said, I am the Rainmaker. Yeah. Harvey called him. What the fuck does that mean? He thought he was going to get sued. Didn't he have some quote like, wait a second, those things make a shitload of money or something like that? No, his quote was the Grisham movie. And I said, the Coppola movie.

And he goes, all those Grisham movies make $100 million. calculated that the faster he could get Good Will Hunting onto the screen he could piggyback off of what was potentially a really big movie. It ended up not being I don't remember what the Rainmaker made but it didn't make $100 million but it was good. What's funny though is over and over again Hollywood

tries to go for these proven whatever faces and the ones that take off so often are the ones, like what happened with you and Ben in Good Will Hunting. People love discovering new stars every once in a while, but Hollywood never seems to realize that. It's okay to give somebody their biggest break. Sure.

It certainly worked out for you guys because you guys became the marketing campaign for the movie. Yes. It's like, oh man, all these guys, they tore it away and it was such a good cinderella story it became part of the reason to root for that movie it was also a very good movie there was a great quote of one of the marketing people we had a meeting at miramax before the movie came out and this guy came in and he goes i can't this story is so unbelievable about the backstory of this movie. It's like the most unbelievable thing. And there's this pause and he goes, and it's all true.

I remember thinking like, oh, okay. So normally you don't normally have the benefit of it all. Right. You have to like fudge some of it. Yes, it is all true. So enjoy that. Did you know it was going to hit like it did? No, no. I mean, I, Ben and I always said

we were making a, we say, if it's just a videotape on our mantle, like we want to like it, we want, we want to like it. And that was the only kind of yardstick by which we'd measure success or failure because we assumed that no, that it wouldn't be a big hit. You know, we were, you know, if it was, if it was bottle rocket or if it was, you know we were you know if it was if it was bottle rocket or if it was you know what i mean if it was a movie that we loved but like didn't make 100 million dollars that'd be fine with us um it was pretty tough for that to happen with rob robin williams being in it well that changed everything yeah that changed everything and that part had been you know we called that our harvey kytel part because because, you know, we called that our Harvey Keitel part because of Reservoir Dogs.

And we had heard that Reservoir Dogs got made because Harvey Keitel said yes. And that got the funding. So we said we need a Harvey Keitel part. you know from a harvey kytel or a de niro or an ed harris or a you know or or a huge massive star like robin or tom hanks or somebody like that um it could have gone meryl streep you know what i mean we could have some rewrites and then it becomes more of a son mother relationship yeah it could have gone morgan freeman you make morgan from roxbury and he's from and then you and then you bring in kind of elements of racial tension around Boston, you know, that both of them would have been steeped in.

That wouldn't have been hard to pull in. Right. With the Wilhutton character. Right, right. Guy from Southie, right? Yeah. At that time, right? So it was made to be a part,

to be kind of as flexible as possible because we were just trying to get it made. So that was kind of a bit of calculation i guess but once robin took it robin robin you know what was it like to be on the set on him because he was so freaking famous in the mid 90s yeah that was our first big exposure i mean i had maybe two days of working with denzel uh on courage under Fire and but we were on like a military base I think and and so it was pretty contained and I shot with Meg Ryan out in the desert but we were way out in El Paso and and that was so there wasn't a lot of that craziness but with Robin in Boston yeah

it was nuts I mean it was it was people hanging out the windows and a lot of people would scream Mork when he walked by. I mean, it was only 15, 16 years earlier. I guess so. I mean, to us, it seemed like so long ago and his body of work in between had been so vast and kind of, if you think of the movies that that guy had done. Yeah.

From, you know, the Fisher King to Good Morning Vietnam, the Dead Poets to just on and on and on. And then all the Mrs. Doubtfire. I mean, you know, all of those massive Jumanji, all that stuff. So to be calling him Mork seems a little... That's classic Boston. You call that Boston, yeah. I know who you are.

Yeah, hey. I know you fucking Mork. Don't try to be something you're not. Who are you? You think you're better than us, Mork? Yeah, you think you're better than me? Come on, Mork, stop it. That was the best thing about the Will Hunting character for me.

I haven't spent so much time in Massachusetts. Like the perfect, you think you're better than me kind of edge. Right. There just hadn't been a character like that. Or Chucky or any of those guys yeah what was the cole hauser's character name bill billy bill it's a good engine it's a good like that guy i knew those guys well cole uh did this incredible thing while we were making the movie like uh he gave away almost all of his lines to case. Really? Yeah. He goes, look, guys, I see that, because we'd written it for him.

And he goes, and we'd written the other part for Casey, obviously. So he goes, I see that you guys, like, are trying to pad the part out to make me want to do it. He goes, but I want to do it because I want to do your movie with you guys. And he goes, and in every one of these groups, there's always one guy who's quiet. Yeah. He was right. Yeah. And he's right. And each every one of these groups there's always one guy who's quiet and yeah and he was right yeah and he's right and he's serious like there's shots and you look at him you go like i do not want to fuck with that guy at all like he's he's the quiet guy who is also the first guy you want if anything if shit goes down exactly he's the guy and and and so he did so he wrote him his own lines he just gave him to casey because

there's always a loud mouth in the group too right right is there ad-libbing or had you done this stuff so much at that point there was no casey there's there was you know because he had lived like the baseball glove scene and some other stuff the baseball glove was just in the house where we were and he came down with the glove that's why i'm laughing in that scene i'm not even supposed to i'm not even supposed to be laughing it's like you know um i just couldn't help it he was so funny and he also like the first day of shooting um we were shooting the scene where he was asking for his line was can i get my double burger and and there was this old show remember when we were kids uh it was called uh what was it uh it was that game show big bucks no whammies oh yeah press your luck press your luck so we always watch press your luck like if you were homesick you're like watch press your

luck and ben and i've really early on started talking about acting you know you they say you make choices right you make a choice you take you know that's a bold choice or whatever we talk about it in terms of going into the whammy business like if you were you know the the point of press your luck is you know you're trying to press the button and you don't want a whammy if you get a whammy then the thing takes all your money away yeah but if not you can make a few thousand bucks or whatever and uh but we always talked in terms of how much are you risking like what are you you know are you just playing it straight down the middle or are you going to go into the whammy business a little bit and and and you know i don't know drop a bunch of weight for courage you know what i mean uh you know whatever any any little kind of moves we'd made career-wise chasing amy was

chasing amy was going into the whammy business right so we talked about that and uh and the first take on casey uh he's sitting in the back seat and he literally goes chuck can i get my double burger and ben and i turn around and he's like, what the fuck? Like, this is the thing we wrote. And he just looks at us and goes, sorry, guys. I'm going deep into the whammy business. And there's nothing you can do. You're like, all right, let's go.

And he's brilliant in the movie. And it really works like that. He brings something that no other character is doing. And it's like the right color for that. So the movie takes off. Yeah. You get Rounders. Yeah.

Rounders is your next movie. You've already decided to do Rounders before Good Will Hunting even came out or did it already come out? No, it hadn't come out. We started shooting Rounders in December of 1997. And so Good Will Hunting came out out i think it was december 11th 97 and it opened in la and new york and then and then it opened nationwide in january so the first month of that movie goodwill hunting was kind of coming out to really good reviews. And I was doing like talk

shows and interviews while I was starting to shoot Rounders, like to promote it, you know. And then it got going. And then it got going, yeah. Why Rounders? What was it about the script? What jumped out at you? Well, so when Harvey bought Good Willwill hunting from castle rock he got ben and i both in these option deals that um you know he had a lot of leverage on us he could have asked for 10 options i think he asked for three each which basically meant i pre-set your price for three movies yeah and i remember saying to patrick and ben at the time like

fuck if if me because miramax was making the best stuff back then and it was like it was like all the quentin stuff and anthony mingala and i was like they want to preset my price to whatever they want i'll take it you know what i mean it's like you know we wanted to work yeah um and then when goodwill hunting blew up and it looked like it was going to blow up, it was like, well, you, it's like a rookie contract. You just try to, you get through it and so that you can go out onto the, you know, and, and, uh, and, and, you know, get, get more money to do the same thing. You're like Jason Tatum on the Celtics. Right.

You know, you know, the big nine figure contracts coming down the road. Exactly. Just try to win some games. Not to compare myself to the great Jason Tatum. You know the big nine-figure contracts coming down the road. Exactly. Just try to win some games. Not to compare myself to the great Jason Tate. I didn't mean to. I didn't mean to besmirch his great day.

Yeah, please. But it felt, but it was like, oh my God, we're, you know, like we're taking off. And the three movies, I was just thinking about this

before you got here, because the three movies that I did to fulfill those obligations were Rounders, Dogma, and The Talented Mr. Ripley. Wow. Yeah, so Harvey had three good scripts. So I just lined them right up, and I did them and knocked them out. And then I never worked for Miramax again, which is weird because I'm one of the people who's really connected to that time. And I mean, I guess I worked for him a lot in that time.

You got dragged into the Harvey stuff and it was just weird. It was like, yeah, you worked for the guy. I don't even know what your role is. I'm not going to ask you about it. And it's not like I'm wussing out because, oh, no it's like i just don't know what you're supposed to do in that situation i don't know i think a lot of people said you know well you knew or everyone knew and i always just said but knew what like i don't i've worked for i don't know how many studio heads at this point i have no idea what any of them do when they go home i don't hang out why

would you know i wouldn't like i if they they go home. I don't hang out with them. Why would you know? I wouldn't. If they were my friends, if I was rolling around with them, and then- But you're going to Vegas with them on the weekends and shit like that. I never hung out with any of these people. They're my bosses, right? They say yes or no to movies that I want to do. And so we're connected for that six months.

And then we take a picture at the premiere and then, you know, they go off and make other movies and I go off and make other movies. So, but I just feel like, like that, you know, when all that stuff was coming out, I think there was so much that was systemic about it that I think that's what people went well fuck everybody around him must have known everything yeah and that's just not true that's that's not what happened and then i started to think about like how connected i was to him and then i was like well wait a minute i haven't worked for him since 99 like i didn't realize you only did the three and then you i didn't either by the, that's a fantastic quartet.

It's great. No, to his credit, because option deals, people normally, they can get stuck. You can get stuck. You can get forced to do something, right? Yeah. I got to come out of there with Good Will Hunting and Rounders and Dogma and Ripley.

It was great. And All the Pretty Horses was a co-production with Sony. But it wasn't part of my deal and I think and then in 03 I shot the brothers

Grimm for Dimension who was which is Bob Harvey's brother let's take a break to talk about Quip the truth is

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you'll get your first refill pack free with a Quip electric toothbrush. That is your first refill pack free. And you're going to need those refill packs at getquip.com slash BS. G-E-T-Q-U-I-P.com slash B-S. Back to Matt Damon. I think one of the best defenses of your career, like if you're an athlete, people are making the cases for you, like with Brady.

People talk about Rodgers as the GOAT. I'm like, well, Brady has five Super Bowl rings and threw for 505 yards in the last Super Bowl, and Rodgers has one ring. If we argued about actors that way, the Goodwill hunting rounders, Ripley, those three characters are so different. It's good.

It's a good feather in your cap. Ripley's fucking creepy. That movie's on all the time. Yeah. It's on the cable. It's, it's really weird and disorienting and unsettling. Anthony was really, really locked in

and really knew what he wanted to do. I remember loving it when it came out. And it didn't really get the do that it deserved. It didn't get nominated for Best Picture. No, it's belatedly gotten it, I think. I hope so, because it was really well done. But I remember thinking, well, if I wait 10 years, because you see the movies right when you make them but it's kind of impossible to judge them and I remember thinking if I wait 10 years

then I can watch and then 10 years passed and I was like that's maybe 20 years and now it's like 20 years has passed on all these things and I still have to sit down and watch them because I feel like I could be more objective it's just it's harder to watch myself young actually than it is to you know watch rough cuts of shit i'm working on now i had denzel was on the pod two months ago and he just doesn't go backwards at all he just goes to the next job he doesn't i understand that i i i yeah i mean and that's that might be where i end up because i haven't been able to go backwards yet either and and um you know we did a they had one of these you know uh 20 year things but it was a the new york times does these readings of screenplays but they cast

them with with different actors yeah and so krasinski was i had dinner with him last year when he goes i'm directing the goodwill hunting one and he goes would you ever do it would you do the reading and i go when is it and i go actually i might be in new york then yeah i'd do it and then i called ben and ben was going to be in new york and so as a surprise we came out and we read our script and neither of us had read it you know literally since we the production draft was the last time you don't go back and you never revise it again it was like that was it that was and we read from and it was a really emotional thing like I didn't had I realized it was way more special than like the academy award anything like had I known it was gonna it was just this thing Krasinski was like will you come do this and I was like sure and it

for Ben and I both I think it was a really like when we got in there and we heard the energy of the crowd and people knew it was like they knew these lines it was like holy fuck you know this 20 years later like it really was special and uh and no that movie definitely has long legs because like we do we do this rewatchables podcast that where we basically deep dive these different movies we did midnight run ironically which is one of my favorite ones ever it was like one of the lowest listened to podcasts out of all the rewatches is that right oh my god goodwill hunting i think was the number one highest and we've done like i mean we've done probably 60 movies at this point but i think that's just become one of those it's like the definition of a rewatchable which is why we want to do this rounders thing because rounders was another one that there was no sign at all that this was going

to happen with rounders not at all in fact it lost money it was pulled from the theater in three weeks we lost yeah it was and i mean i remember my whole life was changing right yeah in a real as you're filming rounders yeah and and in this really profound way to where like it's like it's just your code gets rewritten for the matrix right so just your subjective experience changes yeah the world is exactly the same but it's totally different for you and it's such a mind fuck and i see why people go crazy and they, you know, people without a solid support really get fucked up. And cause it, it's a, it's a head trip. Well, cause it's, you're doing the same thing you're doing every day, but everybody around you is acting differently. Right, right. Exactly. Yeah. And it's a very, it's just an odd and

unrelenting experience. Um, but I remember the, the, the positive part of that was while your life is imploding my career was exploding and i was getting to do this thing that i always wanted to do which was work all the time yeah and so when john doll showed up i was cole hauser was away doing a movie and i was house sitting for him and i remember when john came and met me we're over in griffith park at cole's house and and I I was like because Harvey was like you want to do this movie I was like yeah and he was like well for directors I was thinking you know John Dahl and I was like you mean Red Rock West and The Last Seduction like fuck yeah really will he do it and Harvey's like yeah he'll do it and so it's like suddenly we got

John Dahl and it's like oh my god I love this. And then I meet him and he's like, well, for this part of Worm, you know, I was thinking maybe, you know, Edward Norton. I'm like, Edward Norton? You think he'll do it? He's like, yeah, he'll do it. And it was, he just kept naming these. It was like John Turturro. And I was like, are you fucking kidding me?

You know, and I couldn't believe that all these people wanted to. Malkovich. And then Malkovich. Yeah. Who was just like. Did you know anything and I couldn't believe that all these people wanted to. Malkovich. And then Malkovich. Yeah. Who was just like. Did you know anything about poker? No, no, no.

I mean, I played in kind of the classic home game, like with my dad, where everyone, you bring chips and dip and you play these fucking stupid games, you know, like baseball. And like, you know, it's like, you you know there's 18 wild cards and some guy wins a hundred dollars somebody loses a hundred you know but nobody really gets hurt and you drink beer and like that was poker and so part of the you know getting to know you know brian and david and you know who end up being lifelong friends of mine and who yeah but brian was, and David were both very dialed into what was then this really cool underground scene. You know, it was, you had to go like, you got to go look up into the camera and get buzzed through a steel door. And, you know, it felt like, fuck, this is cool. Like, yeah, this is a world. This is a whole world whole world yeah this is subculture that i didn't know existed and um you're kind of the poker profile smart competitive guy yeah though now it's like

poker is dangerous for us but the game the game is now like so far it's evolved like i don't know how many you know but you guys started playing though right we did we started playing but i got into it yeah i mean we got into it like but not to the extent that somewhat like toby mcguire is a fucking legit poker player like he's really good uh ben won the state title out here in california 14 years ago or something he got really into it but even since then the game has really evolved i mean it's all deep deep game theory now and these kids coming up on the internet are watching they're playing 10 hands at once all day like they've seen you know they've seen every variation they've seen every variation of

everything and a lot of the times they're playing because they don't want to get their their play you know it's like it's like that great there's a great play in football last year where Tony Romo where the Patriots let it let up a score at the end and Romo just goes oh my god that's so gross he's just doing that to mess with the analytics because like it's a meaningless score and he never puts five people here in the body he's like he would never do that you know he goes he's just doing that so that it looks like sometimes he does this and sometimes he does that no when it matters he does this and only this and it didn't matter. And so he's just fucking with the other coaches right now.

And that's what these people playing poker now are just, are playing a game within a game, within a game, within a game. And it's just so far beyond them. Like the math, like I was talking to Brian about it recently, like the math, you just have to be just lead pipe on the math. It's like, that's a no brainer. But the game theory beyond that is just, it's beyond my comprehension where the game's gone.

They told a story that we have in the oral history about they were playing poker with some guy who was a friend of yours and was talking about movies. And they were like, we're doing this movie. And they're like, no way. And he ends up calling you and Affleck and you guys showed up and played poker. And that's kind of the first time you all hung out. Yeah, we're doing this movie. And they're like, no way. And he ends up calling you and Affleck and you guys showed up and played poker. And that's kind of the first time you all hung out.

Yeah, it was at the bike. You remember that one? Yeah, yeah. A friend of ours was at the bike and he called up and he goes, there are these dudes down here who said they wrote your next movie. And that was before, I mean, that was really early on in the whole thing.

Like I don't think I'd met Dahl at that point. I think it was like, we're going to get John Dahl. And it was like, wait, the guys who wrote rounders are like i'll be right there yeah yeah and we went and went and hung out and i watched brian play because i didn't play hold him i didn't you know and then he gave me i mean i remember he gave me like the super system and he gave me but you know kind of the the all the books that were that were kind of relevant at that time and but that year i mean to promote that movie we we they bought edward and i into the world series and that's smart yeah i actually remember

knowing about that when it was happening like people writing news stories about it right right right and it was and it was 20 grand they were going to lose and they got all those stories out of it because um but it was 350 people yeah and they announced that year i remember i believe it was 350 so you're 350 or 700 but whatever it was it had doubled whatever the last year's entries had been and they were like and there was a big cheer that went up in the bin at binions because is it true you lost to doyle brunson he knocked you out yeah i had kings he had aces so that's a true story because that was on the internet i never know yeah yeah you know that's true that's you lost to doyle brunson who's so famous he has a hand named after him yes the 10 deuce he knocked you out with two aces he did

and uh which was great because i'd been sitting there i mean playing like a donkey i mean i was just sitting there just just yeah not doing anything because all i was thinking was i gotta last as long as i can. I can't go out in the first session. I got to go to get to the piss break. And then I got to, you know, I, you know, I wonder if I just donk off all my chips, like, can I make it to the second day? Yeah. Right. Cause that would be a good story. And, you know, and then I, then I got Kings and, and there was a raise and a re-raise. I mean, in retrospect, I could have got away from him, but I also, I had $6,500 in chips at that point.

And I'm like, it's Doyle Brunson. This is going to be good either way. I think that's a good, I think it played out pretty well. No, it did. And I remember- It's like going against like Belichick or something. Yeah, you're just like, what the fuck? Nobody expects me to win.

I'm just going to, it's like Pete McNeely. Yeah. Like, I'm not going to sit in the corner. I'm going to come out and just throw haymakers and confuse the shit out of them. But I think this is the problem with these guys 20 years later. And this work, cause there's so many people in the world series of poker and people want to have their story of going head to head against the pros. And I think it's hard for them to win now. Cause they don't know what anybody has. They don't know what anybody has. And people aren't playing with any discipline

because they're behaving differently because they want to say that they played with Bill Simmons, right? So I got involved in a hand with him. So yeah, it's become really hard for them. Did you think Rounders was going to do well? I never know if anything's going to do well. I mean, I liked it. Because you think about,

this is one of the reasons we wanted to do oral history. It was one of these slow burn movies that the 90s had that doesn't really happen as much anymore. You still see it sometimes. Like John Wick, I think, was an example of like, it came out, kind of came and went, and then became a thing. But like this happened over and over again in the 90s.

It happened, Swingers, Dazed and Confused. Rounders was another one. It came and went went it was the first matt damon post goodwill hunting movie and was gone in three weeks and then it started showing up on cable yeah and then and then well and then poker then poker started going that really helped i think you know when when uh the uh world poker tour and you know you started to see people's whole cards and watch how they played and it just people it just caught on and the game exploded after it came out where poker people talking to you and like did they feel like it was their movie what was the reaction yeah i mean

you know poor side l still is like every time i see him he's like oh god man he's like you killed me like showing the worst moment of my life you You know, it's like. We were talking about, we did the rewatchables. We were talking about how he's the big loser of that whole movie. Because he had like a top 10 career. Oh, he's a genius. He's in that Raiders movie as the guy that gets worked. Yeah. And he's an incredibly nice guy.

Like he's, you know, he's a guy you really root for. So no, he was like, yeah, through no fault of his own became yeah was the big loser in that whole thing Mike McD yeah what's your mindset with Mike McD because basically this guy just has a gambling problem and he's full of shit

and he's got this one friend that he loves but now you gotta take that and turn it into something yeah I mean I don't know cause that's like a leading man but now you got to take that and turn it into something. Yeah. I mean, I don't know. Because that's like a leading man, old school leading man. You got to carry this.

I have to root for Mike McD. Right. I think you have to believe that what was probably more the case then, as you were just saying, like that he was a top 10 player and that it's not gambling gambling especially back then right like there was a lot more soft money around like people know how to play the game it's like jujitsu now like everybody knows the guard right but like 20 years ago um they didn't and 20 years ago player of that skill level would you know actually could probably live pretty well. Right. You know. What do you remember from the Coppola Levine script? Like, do you remember thinking this is rich and different and feels like I haven't read

anything quite like this? Yeah. Yeah. And I just remember believing all of the relationships. I love the way it, you know, the relationship with the the worm character it's just everyone has that friend you know what i mean and you're just like fuck you're just nothing but you're just nothing but trouble you can't you know it but you can't the black cat in your life yeah and you just see it with every decision they're gonna make they're gonna make the wrong decision just like you're

gonna get fucked you're gonna get your nose wrong decision. Just like, you're going to get fucked. You're going to get, your nose is going to get broken. Like, right. You know, but not because of anything you did. Do you think Norton could do that? Cause Warren was such a scumbag.

He hadn't really played anybody like that. I think a guy can do anything. Yeah. Yeah. I mean, he, you know, at that point he'd done Primal Fear,

but the, you know, the people versus Larry Flint was, you know, and he was, he was working on American History X. He had shot it and he was uh in the editing room and he gave me a rough cut of that to watch like while we were making rounders

and i was like holy why didn't you talk him out of the two-hand reverse dunk in the pickup game well i mean there's a certain point then you're only talking to somebody's ego and it's not worth it you know dude that you, that, you know. Come on, man. Just make it a one-hand facing the rim. The thing on the curb is unforgettable. Oh, my God. But, like, the two-hand dunk is unforgettable for the wrong reasons. So that movie takes off.

But belatedly, it's like this belated success. It's like you get bounced from the playoffs in year one or in round one, but then five years later you find out that you actually like won some award that you didn't realize you won. You're the Sacramento Kings. Yeah. You're the Sacramento Kings. You're like the more victory champs.

You're the O2 pseudo champs. Yeah. I mean, well, it's also the business is so different. Like there was a DVD market, right. And it's just evaporated.

It's gone. So that was, I asked the studio head recently when we were promoting The Martian, I asked Jim Giannopoulos, what was the real effect of that? And he said 50%. 50% of business has been cannibalized by, well, it's just technology, right and yeah it's these different

ways to deliver this stuff but but in very real terms for us that's why the movies have changed that's why they won't make rounders anymore they won't make goodwill hunting they can't um they would make it if he was a superhero yeah but i mean so if he but they wouldn't even make rounders he came from mars to play poker well see what it's been kind of replaced with is the international box office right and so what you want are movies that are big and really understandable to people all around the world across language and culture yeah that means talk less make things more simple white hat black hat superheroes like it makes total sense right everybody knows who the good guy is everyone

who's the bad guy is and and you know and they spend 400 million dollars and blow a lot of shit up and like you get your money's worth and and um conversely you can't put rounders or goodwill hunting into the into a movie theater up against that stuff see i'm wondering if netflix is gonna fix that to some degree everybody's wondering that everyone's wondering what's gonna happen. Because think about just what they've done with like rom-coms and like teen comedy, like the stuff my daughter likes. Nobody was making those movies for eight, nine years.

And Netflix clearly had some algorithm. And they realized like, oh, like your daughter or my daughter, it's like they're underserved. Let's make movies for these people. I hope so. I mean, look, there's like the movie that's really gone is like the $20 to $70 million or $15 to $70 million drama. There's just, you know, a lot of that's migrated to TV. And yeah, all right, so.

Well, Rounders is the type of movie that's just gone. Yeah, and i remember seeing i i saw we took behind the candelabra to uh the can film festival because it was an international release uh in theaters theatrical release but here it was on hbo and i saw harvey weinstein at uh at the can and i hadn't seen him in and i hadn't seen him since he had passed on behind the candelabra so i asked him i was like what why did you fucking pass man this is like classic miramax movie and he remembered it was a year later and he or a year and a half later and he was like it's a 23 million dollar movie i gotta put at least that into pna that 50. I got to split it with the exhibitor. So now I got to make $100 million.

Now, I like you and Michael and I like Steven, but do I believe that movie's going to make $100 million? Definitely. And once it does, then I start to see profit. He goes, that's a tough bet. He goes, now that I've seen it, I should have done it probably. But he goes, it's just really, because that's the business. And so if you don't have a DVD behind that, right, that are these other ancillary monies that are going to that are going to backstop you. It's a it's what ends up happening. Right. So I produced this movie Manchester by the Sea. Yeah.

A year or two ago. That's a classic movie like we made it 20 years ago. We would have made it for 20 million bucks, right? We made it for 8.8. And, and we only got 8.8 because Kimberly Stewart, who runs K period came into, came in and like independently financed it. The best other offer we got was 4 million bucks from Amazon. And we were like, we can't make it for four. We can barely make it for eight. And. But what's sad is that movie was exactly the type of movie you and i grew up with yes and the kind of the kramer versus kramer type of movie that got made

the verdict all those movies got made over and over again my entire childhood yes and that was the kind of that's why i wanted to be an actor were those movies, right? Those kitchen sink dramas. And the problem is that you can still make them, right? Nobody gets paid any money. You know, the crew gets paid and, you know. Well, now you have to hope it's like, and you're basically making it to try to win an award. Right. And the only reason we won some awards with that was,

I mean, not the only reason, I'm very proud of the movie, but Amazon picked us up after and kind of were using us to prove themselves as a prestige content provider. So it was like getting hit by a bus. Yeah. I mean, I talked to marketing people from other studios who were like, they've probably spent 40 or north of $40 million on the campaign for the movie, right? So it was suddenly everywhere. That was because we had this big engine behind us. Well, they were trying to legitimize their own business right so we were we were just in the right place at the right time but going back to the production side of it like had we had more

money to make that movie you know i love manchester i'm incredibly proud of it but kenny had an ending there was this scene where they were all on these boats. They were on the boat that the whole movie's kind of about. And it was a flashback to before Casey's kids had died, before his brother had died, when he was still married to Michelle. And it was this thing. They were all on this boat and they were whale watching.

And it's this incredible moment of joy. And you see this family all together. And then these whales start breaching out of the water and it's just and you needed fucking drone cam and a fucking i mean it was one day of shooting right and you got to get lucky with the whales but either way like we could have figured that out but it was that it was this epic and so with as the camera pulls back as this family has experienced this incredible joy and you know it's about to go horribly wrong for them right the camera's pulling up up up and it reveals all of these other boats all around it and it's all these other families that are watching these whales right and it's like this is one little story in this sea of stories right and it was epic and it

was beautiful and it like tied the whole thing in and it was and we ran out of money you know what I mean and it's like fuck like if in retrospect like we could have done that but you don't know that it's Manchester until it comes out and everybody goes holy shit it's great you know I mean more often than not it's so hard to make those movies work and there just used to be in the 90s so much more the margins were so so much greater that you had more money to swing and miss with. And as a result, you got better stuff. One more break to talk about Hotel Tonight. Here's a little insider travel secret from our friends at Hotel Tonight. There's a ton of empty hotel rooms out there just waiting to be booked. Booked, booked, booked and books. Booked. Hotel Tonight has partnered with these awesome hotels

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Start scoring amazing deals in incredible hotels. Go to hoteltonight.com or download the app now. Back to Matt Damon. What's the most surprised you've ever been that a movie you made didn't work? There have been quite a few, man, that I really wished worked better downsizing i was really bummed out about um you so you thought that was gonna hit no i just thought

well i thought the critical response would be better because because i believe we made what alexander told me we were gonna make which was a hal ashby movie with special effects you know and it's so fucking weird. That's a good soap job. It is. It is. It was perfect for me. That was all I needed to hear.

But it takes this such a bizarre left turn, right? That's so insane, like that they're going down the fjords in Norway and he falls in love with this one-legged Vietnamese political dissident who ends up, you know what I mean? And yet it's all this life-affirming kind of, and it was so bizarre, but wonderfully bizarre that I thought, I thought film critics would go, this is the fucking kind of thing that people need to be making more of. Like, I'm so glad somebody put money into the, and instead it was like the opposite. It was like, what? Kristen Wiig doesn't get small and they don't have, it's not a screwball comedy. Like

what's going on? And I just, I was just shocked by not shocked I mean never shocked but I but I was I I would have bet that one wrong I I bet obviously I mean I'm in it you know what I mean they're all bets I guess to a certain degree like you know where I stand based on whether I said yes or not well the flip side of that would be the Martian right you knew that was going to be potentially good but you didn't know it's gonna be like no and there was a lot more risk in the martian because it was just me and it was going to be perceived as just me and i remember having that long conversation and going like all right do i do this this is if this one misses it would be bad right because it's a lot it's it's it's 110 million dollar movie i mean ridley did it for 108

and you're in half of it by yourself basically yeah and and it's it's it's a it would be a it would be a kind of a personal rebuke if people just were like fuck that i don't want to see it you know what i mean like it would be hard to whenever one of these things doesn't work you're always playing that shell game right your agents out there going like yeah but here's what happened here's what really happened yeah yeah and and to a large extent, that's true. You know what I mean? I always tell people, you don't see the movie before you make it.

You get the ingredients for whatever you're cooking and you get to see what the ingredients are and you go, all right, with all these people around, we should be able to do something pretty good and or hopefully great like ideally you're starting out everyone thinks hoping that it's great and eventually you end up with something you know good and and some of them just don't work and i think it's like baseball you can't go four for four every game every game right yeah i know you want to go two for four every day every day right yeah i know you

want to go two for four three for four with a dinger right occasionally you might go four for four and sometimes you're gonna go for four but i mean you've now this is like 25 years you're cranking them out yeah there's gonna be a couple downsizes that go there you go oh man what happened yeah and yet looking back on it like i don't i would take that movie again i mean alexander payne i mean that's the first movie he had that wasn't a critical and box office hit you know maybe i killed him the only one i would have stopped you from was the golf movie you couldn't swing a golf club i'd never swung one i know i had less than a month to learn i talked myself into that you speed rushed a game that you cannot,

but, but I know it was, and, and also just, it would just look, don't get me started. It's, it's over 20 years and it's still painful, but I look, I really, really wanted to work with Robert Redford. Yeah. Um, and, and ordinary people was kind of a touchstone for us and, and yet another movie that wouldn't get made now. Right, right. And I got a lot out of it. I got a lot out of working with Will. I loved Will. I mean, what a gentleman that guy is and really does it right.

So it seems like you were trying to have experiences with different types of directors, stars, whoever, like trying to gleam certain things from whoever. Yeah, not making- Which is smart. Not, what's the saying? Not making great the enemy of good. Like just working. The other thing was this whole upheaval in my life was happening

and I'd get more uncomfortable when I wasn't working. So I just, I really put my head down for like five years and just stayed on the road and worked and felt very protected in, you know, among movie crews, among, you know, there was none of that fame shit and none of that stuff kind of infecting those dynamics. Did you see what was happening from the outside with you and Affleck where people were kind of pigeonholing you as these two? Like Affleck somehow became the guy from the movie. Yeah, yeah. From Good Will Hunting. You were like the smart guy who was making career choices and he was the dumbass who's just making big budget movies. Yeah, and that was really hurtful, to be honest. honest like i remember the first time was saturday night live seeing saturday night live and they portrayed ben as like some fucking neanderthal yeah you know who literally couldn't talk and

it was so offensive and so not true and so kind it's like i you know and and also so we shot goodwill hunting i remember ben we were in after seeing like a rough cut of the movie or something we were with at miramax and uh ben asked harvey to please call michael bay because he was up for this movie this movie armageddon and i remember thinking oh that's really smart because maybe maybe michael bay will listen listen to Harvey or maybe that'll tip the scales for you. Like I would have done Armageddon. Yeah. Just, we had no idea where things were going to go for us. We needed jobs. Right. And I had, I had lucked out and been cast in Saving Private Ryan. Right. So, so those movies came out the following summer, Armageddon and Saving Private Ryan came out the same summer

and then it was like oh Matt's the serious guy and Ben's the big popcorn movie guy and it was just like no I mean we would we would have done the other job you know what I mean there was no so so it was just terrifically unfair and then and then it took a long time for Ben to kind of write that ship publicly privately everyone who knows ben knows ben but but it wasn't until i think you know he started directing and and started directing some really good movies and then won best picture that people were like oh fuck he's really smart you know yeah his career's had a lot of incarnations but it's been a lot of things that we've seen before with other people's careers you

know like hollywood loves a comeback yeah yeah you could see it when he did gone baby gone it was like oh affleck he's back it's like well right we were all bearing him like it's yeah yeah exactly he was there the whole time yeah yeah and and i think he, whether he internalized that criticism, I don't know, but certainly he seemed, he handled it way better than I can. I'm, I'm way more thin skinned and maybe that's why he takes bigger swings. Maybe he's like, fuck it. I'll play Batman. You know, I never would have done that.

I'd have been like, why? You know, the downside. Why? Don have done that. I would have been like, why? You know, the downside. Why? Don't do that. I actually did a mailbag when I was at Grantland, and somebody asked me why Ben Affleck did Batman, because he was, you know, he was on this great run. And I was like, this is kind of like his fuck you role.

Yeah. Everyone had counted him out. He made this huge comeback. And this is like the 07 pats thrown deep to randy moss when they're up 48 to 10 right yeah he's like fuck this fuck you i'm telling you i'm gonna be batman i think that's true and i think there's also the very real aspect of his son was three and trying to impress your son yeah yeah yeah and people don't realize that i just want to impress their kids i remember being at ben's birthday party years ago and and to impress your son yeah yeah yeah and people don't realize that just want to impress

their kids i remember being at ben's birthday party years ago and and toby was there and ben and toby had a conversation about and toby was just talking about what his son thinking when otis sees me he goes he's you know it's a real thing man it's fucking cool my kid even for a couple years thinks i'm spider-man or thinks you know and and so i think that was definitely a very real component to him doing that so when you make and also because ben classically thinks he can fix everything he is he is the most optimistic i've said this about him for you know we used to go to movies and we'd come out and our whole group of friends,

what'd you think? Well, that sucked. That sucked. Yeah, but you know what would have made it better? This and this and this and this. And he would literally just do, just script doctorate in the parking lot. And suddenly he'd make a movie that everyone wanted to see. And so early on in his career, I think he got put in these situations where he knew how to script doctorate and they weren't letting him.

And so then, so what directing allowed him to do was be the person making the decisions and that's why the movies that he directs are really good um because you you never wanted to you never really wanted to go down the directing road i do i i really want to direct and i i almost directed manchester i almost directed promised land which is this little movie about fracking that's right you Manchester fell through right you were supposed to direct that I was going to direct it and then I was and then I decided and then I was like wait I'll play the role because Kenny

Lonergan had had a really bad experience with his previous movie and it was when I read the script I was like Kenny man you got to direct this this is you know this is not a writing assignment. Like you, you got in there and this is, this is your story to tell. And, um. Maybe you can direct the father of the bride remake that you're going to do to impress your daughters. Actually. If you want to impress your daughters, remake that movie. Make this, make this sequel.

Oh God. There are movies like that that we could bring back around I'm sure that would that one I mean there's some there you know this there's some certain

dad daughter movies that are out there yeah and that's like one of the icons but yeah I think with Netflix throwing around the money

I forgot to ask you before we go Rounders 2 yeah it was gonna happen every time I saw you I asked you about it and I was like

Copland wanted it to happen it's not happening it's 2018 well I mean you know we had Copland and Levine

had a whole pitch they pitched it to Harvey Harvey said yes in the room and then never called back and so I'm pretty sure you guys They pitched it to Harvey. Harvey said yes in the room and then never called back. I'm pretty sure you guys could get Rounders 2 made.

I don't know. I mean, it'd be interesting. Like in this, you know, I mean, what would it cost? I mean. I'm pretty sure Netflix just greenlit it listening to somebody at Netflix right now. Well, we do it. If Netflix wants to do it, we'll do it. I mean, it's a great, like, what happened to these, you know, what happened to these characters? And have they ever told you the pitch?

It's really good. I mean, it's really good. And it's everybody. You know what I mean? It's like, we'd want Dahl to come back and direct. Edward, John, John, you know, everybody, all of us. Like, what happened to the whole group? Well, the best part of the, like the fact that Mike McD

at the end of that movie goes to Vegas. Right. And he's like, World Series of Poker, could this be my day? But it's 1998. Right. I'm watching it. I barely know anything about poker. I don't really know the World Series of Poker.

It wasn't on TV or if it was, I wasn't watching it. But then Moneymaker happens in 03. This movie gets- Yeah, that was a big one. Moneymaker was a big one. And now Mike McD trying to win the World Series of Poker, like it actually made the ending seem so much more realistic. So now if you catch up with him in the late 2000s,

I don't know. Well, and do you think he's Johnny Chan? Like, is he that good? Like, is he one of those guys? And I always saw him as one of those guys, but the question would be, right, the new, these new kids coming up online. And he's like one of those guys and i always saw him as one of those guys but the question would be right the new these new kids coming up on the online and he's like one of the old lions and he's one of the old lions right and so it's like there's these different generations there's the doyle

generation right there's the mike mcd generation right it's like my generation which are kind of caught in between like and then there's the new fucking cyborg generation, right? And these kids are kids, wherever, young men and women are amazing guard players. And so can you beat, can the analog generation, the kind of crossover generation compete with that? And how do all of these characters who are all a part of that generation, Edward and Turturro and Malkovich, and all of those players are in that generation.

So how would they? It's like you and Daniel Negreanu and Phil Hellmuth. Phil Hellmuth and Phil Ivey. Mike McD is like, he's one of those guys. He's in that cohort. Yeah, he's in that group. Yes. So I was thinking, you, he's one of those guys. He's in that cohort. Yeah, he's in that group. Yes. So I was thinking,

you know, Seidel. Seidel. Yeah. Seidel needs a win in rounders too. Seidel needs a fucking win. Seidel should just beat the shit out of me in rounders too. I owe him.

I definitely owe him that. Rounders too, Seidel beats Mike McD in the World Series of Poker. Exactly. And then cries. Exactly. Yeah, I was thinking with, with, with with if Rounders 2 never happens,

I think the natural thing is Billions Season 8. Mike McTee is now a billionaire and gets brought in. I love it. He's running a hedge fund. He's been in a poker game with Axe from Billions. It gets a little heated, and now he decides to destroy Axe. Four episode arc for you. I'm going to take down Axe Capital.

I think you should do it. Just think it. Keep it on your radar. I'd do a four episode arc. I don't know if your daughters would be impressed. That show's awesome too. That show's really fun. At some point you're going to have to go on it.

I would love to, yeah. I mean, I would, I'll have a lot of my friends are on that show. I forgot to ask you, when Malkovich unleashed that Russian accent, what was your reaction in the room? Oh, good. This is one of my favorite stories actually. I forgot to ask you, when Malkovich unleashed that Russian accent, what was your reaction in the room? Oh, good. This is one of my favorite stories, actually.

So the buildup to Malkovich getting there was extraordinary. I mean, it was like, you know, he had one of those deals where he was there for a week. Yeah. And, you know, we start shooting in December. You you know malkovich is coming like february 1st and so for the whole run of the show it was like malkovich is coming malkovich hey kid kid you ready he's coming you know he's coming right yeah malkovich is coming it was like this and he has real gravitas in the mid 90s oh fuck yeah yeah yeah um he's like one of the most elusive talented actors enigmatic that we had yes and he also happens to be one of my closest friends terry kinney started steppenwolf with him and so i actually had a connection to him um that that

that kind of took him a little out of the icon status which was nice which was helpful for me because it was the build-up was like he's coming he's coming you know you're gonna be you're gonna be able to hold your you're sitting across the table from him yeah so he shows up and the first time we roll he goes if you don't have my money then you are mine and they go cut and everybody just spontaneously erupts into applause oh they're just in right away oh they're like fuck he's amazing and it's just me and him yeah and i'm looking at him across the table what are you doing and then they go take take two. If you don't have my money, then you are mine. And again, they erupt into, you know, the crew's like, fuck, he's here.

Malkovich is here. And I just was looking at him and he sees me. I guess I'm like giving him the one eye. I don't even mean to. And he like leans over the table. He kind of beckons for me and i lean across the poker table and he whispers in my ear and he goes i'm a terrible actor it was the fucking greatest it was like it was there was so much in that you know what i mean

that i still to this day like treasure because it's like you have to keep fucking grinding like sometimes people aren't gonna tell you you know which is not to say that i didn't like his performance in the movie i loved it and he and he was and the and the accent he was walking around with a tape recorder the actress from burnt by the sun the russian movie that had won the oscar she had she had recorded all of his lines for him so he was it wasn't that he was he was grinding but but you know I actually think it hurt the first viewing of the movie like when you're in the theater for it but then it gained steam each time well I remember in the theater being like what the fuck is going on he's gonna talk that way the whole time but 20 years later it's like I'm so glad he did it that way. Yes, me too. Me too.

It's so much better. It is. It is. And he just absolutely was like at an 11 for everything, for the whole thing, you know, and it was brilliant,

you know. Can we agree that Mike McD, after he wins the 60 grand at the end, and he kind of taunts Teddy KGB about it and says, I could go on busting you all night, that the Russians just immediately kill him. Yeah, it's amazing that, you know,

there are a few things. There's no way he gets out of there. Well, the other thing I never, you know, he's got, you know, the Famke, Famke's character, you know, Famke Jansen, who you keep saying to him, why don't you come back and play cards? And why didn't, I'm like, why didn't they get married? It was like, she clearly, she like, she kisses him at one point. She's like, she wants to be in

a relationship with him. I'm like, Mike, what's your problem? Like, she seems to get you. You guys really like to do the same stuff. Like this is, so I've known Koppelman and Levine since I wrote about rounders when I was at ESPN a million years ago and this is my number one question I ask them and I bring it up like every two years like she comes back in his girlfriend's moved out his wet blanket girlfriend that just didn't really like him and approved poker

Gretchen the great Gretchen Maul shout her out please yeah she didn't like Mike McDade she didn't support his poker well she was like she she they were in law school together she was like she didn't like Mike McDade. She didn't support his poker. Well, she was like, they were in law school together. She was like, she didn't get it. She didn't get it.

And she was like, you have this shot at a career as a lawyer. Get your shit together. She was way more traditional. And he was like, I can't do that. Well, we didn't need her in the movie. What we needed was Famke comes in. You have no furniture left. You're watching like Johnny Chan, some old poker thing.

And she comes in and me is like, oh, the 1989 World Series of Poker. Watch the discipline. And then she wants to have sex with him and he turns her down. Yeah, I didn't. And it's one of the biggest mistakes in movie history. Yeah.

They know it though, they admit it. I'm not gonna fight you on that one. I didn't get that at all. It's also, it's not even just even like to, I mean, it's just, I mean, she totally gets the guy. You know what I mean? Like the most important thing in his life is the most important thing in her life. Like how could they have, like how did that relationship go off the rails? Because it's like they kind of, I think they suggest that there was a relationship before for them, right?

So it's like, well, what happened? Maybe that's part of Rounders too. Well, he should be, they kind of, I think they suggest that there was a relationship before for them, right? So it's like, well, what happened? Maybe that's part of Rounders too. Well, he should be, they should be married. Definitely. But now the Russians are involved. The Russians, you know, in 98, the Russians, it was like post-Cold War. Not quite as dangerous. No, right.

As they were in the 80s with the Ivan Drago era. And now it's back. They're dangerous again. Right. I wonder how dangerous Teddy era. And now it's back. They're dangerous again. Right. I wonder how dangerous Teddy KGB is. He's dead. I think they killed him after he lost the 60K. We got to bring back Malkovich.

Make this happen. You're a powerful man. Dude, believe me. How many have you made in a million movies? There's so many movies that I can't get made. It's incredible. What are you talking about? I'm telling you, dude. You've made five Bourne movies.

I know. Those are the talking about? I'm telling you, dude. You've made five Bourne movies. I know. Those are the easier ones to get made nowadays. Those bigger ones, oddly enough, are actually easier to get off the ground a lot of the time. You couldn't stop Fever Pitch, though. I know. Well, come on. I love Pete and Bobby. I never saw Fever Pitch, to be fair.

No, we need the right red sox fan the right red sox movie has not happened well they also had their whole they had to rewrite i remember the ending because we won in 04 it did kill the movie it didn't kill us but it killed the movie it certainly didn't kill us i was saying to somebody recently the fact that the the red sox can go in a swoon with the yankees coming at nipping at their heels all of a sudden used to be the worst thing that could happen to me and would ruin my summer and now it bounces off me and I'm not scared at all it's the biggest thing that's changed in my life that's actually fear people who aren't from Boston don't I don't think could appreciate the level to which that is true

and that and that and that that something so deeply and psychically or kind of existentially important changed for us in 2004. Like in a deep, deep, deep way, everything changed. It was like living in a house in a terrible neighborhood and being afraid you're going to be robbed every night. And then all of a sudden you got the best security system ever and you had like four armed guards outside it's like all right i'm gonna know or you just walked out the next day and the neighborhood is really nice you're like what happened this place is fine i love this place god yeah it really um

yeah it doesn't get me the way it used to it just was it was it was like it was responsible for like an underlying kind of baseline of anger i think and like everybody from the greater boston area i remember going to the walking up on and onto boylston street and watching the duck boats go by and just by myself and just crying i mean really you know i was 34 years old and goodwill hunting it immortalizes the fistcomber which was kind of like how we won the world series as red sox fans even though we actually didn't win the series but people felt like we won the world series because we won that game because we that was as close as we were gonna come yeah oh god and aaron boone was a year before it's just a disaster about matt damon um did we talk enough about rounders i feel i feel uh i didn't ask you about the climactic poker

confrontation scene in rounders because that's the last thing we can hit um yeah because in the beginning of the movie you you when he gets cleaned out, and I call that when I wrote about the movie, I called it the Mike McD face, which is that kind of all my money's gone, which is the same face. The reason I think you're able to pull it off because it's a really good memorable face,

but it's the Buckner Shiraldi face. It's the we just lost the World Series in 13 pitches face. And fucking Koppelman's like a Mets fan. Yeah, right. So you're just able to tap into that, do it. They had that line about Buckner walking back into Shea, I remember in the voiceover, which I ended up doing, but it was a highly contested line.

I was just like, I don't want to say it out loud. I don't want to say that out loud. And Brian said, but it's the perfect metaphor. Yeah. It really is. And I said, I understand why it's like, I understand why you wrote it, guys. It's very hard for me to say. What did you try to change it to?

I didn't. I didn't even suggest an alt. I just said, I fucking just give me a minute. And every group yeah it's like it's it's it's like getting punched in the stomach is how and and how and how they referred to it brian and david because brian had been felted a couple times and he goes it's a it's think of it that way because that's the that's what it is it's like a physical it's like someone just just uppercutted you to the stomach it's actually the perfect analogy. And I don't know, even though that movie is 20 years old,

I still think it's the right sports analogy. I don't know what else. No, I don't either. Nothing's really happened since that. It was probably worse than that. Where you have like Buckner Shea. I know exactly what that is. I know exactly how much pain immediately.

I think it still works. So then you have the game. Like Buckner Shea, I know exactly what that is. I know exactly how much pain immediately. Right, right. I think it still works. So then you have the game. Do you feel like you're good at faking being a poker player at this point, or do you actually feel like you're a poker player? No, I definitely didn't feel like a poker player. I felt like, you know, unlike the golf movie, I had about 30 days to learn how to play poker.

Yeah. But luckily there wasn't a physical manifestation like a swing with which you could see. You know what I mean? I got to watch a lot of people play. And so I got to observe them play and see how little they do, you know, because you obviously don't want to want to you know you don't want to tip your hand right so you so but it's a little attitude smack talk too which is there was more back then yeah now guys are just in their sunglasses get the airpods on and you know their hats over their faces and it's like you might as well be playing online but but back then there were there were a lot there was a lot more talking um and uh

and so and brian got me into those games like you know we had a technical advisor named mike selza who ran one of those clubs i think and and uh or new people or whoever it was but he got us in and i got sweat some of these players you know and that's when they allow you to sit behind them and look at their whole cards and um you know, and watch how they're playing the hand. And so it was just, that was all just based on kind of what I saw in those situations, but also the dynamic. Look, I'm a writer also, so I know there's got, you know, there's got to be some drama. It can't be, you know, the hat down and the sunglasses. It's the showdown with, you know, your antagonist. And it's the duel at the end, right?

In the middle of Main Street. And the Oreos. Right. And the Oreos, right? Which is, I mean, a little bit of a tell. Yeah. But the thing is, when I saw that movie and I didn't know that much about poker, I missed it. I didn't totally get it in the moment, you know?

It's so big, right? And in shot and so close up. Such close up. I missed it. I didn't totally get it in the moment. It's so big, right? And in shot and so close up, such close up. As I remember, again, I haven't seen it in a long time, but it almost hides behind how big we made it in a sense because it becomes about Malkovich and it's just this kind of juicy close up. And then later you realize, oh, he's unscrewing the Oreo next to his ear. sense because it becomes about malkovich and it's just this kind of juicy close-up and and then later you realize oh he's unscrewing the oreo next to his ear like it's one of the one of the

biggest tells you could have like the worst tell of all time but uh but the way doll shot it i think was really cinematic and beautiful and kind of we got away with it so rounders two you're ready you're ready for something dude i i've been you can ask koppelman man i've been we've been talking about it we just don't i i don't know if i don't know if uh if if the weinstein company has the the rights to it i don't even know if the wines the wines and company exist anymore i mean i was in like so i don't even know what then what happens i don't what happens to all the stuff they have the rights to? Yeah, they probably own all this IP that they'll probably try to sell off. So maybe by saying I want to do it, we're fucking us

because then they're going to try to rob a bank when they sell it. Or they're just grabbing what they can get. What's that? They're grabbing what they can get when they finally sell stuff off, maybe. Right. Yeah, I don't know. You might need to get Affleck in this in this well he's the real card player i know he plays all the time yeah he's he's he's genuinely good i mean he i mean you have to play so often to be genuine i mean he was he was i mean he was good enough to win i mean he beat 350 i mean it was like tj cludier like they like, legit people that he beat in that tournament.

I think he won. I think it was, like, 350 grand or something he won. He's no Toby, though. No. People are, like, afraid of Toby McGuire. Yeah, I've only played with Toby once. And Ben said, like, don't ever, ever, ever get involved in a hand with him. Like, he is not only, he's, like like the best, you know, celebrity card player.

He's like, it's not even close. He's like, he is, he's just legit by, I mean, I think he, you know, I think that's his major source of income. I think because the other thing is like. Is it NBA players that he's playing poker against? Yeah, a%. I mean, there were, like Annie Duke, who used to train Ben, they were friends and she gave him lessons, right? And taught him really how to play. And she used to get played back at a lot when she was in Montana

because she was a woman, right? And these guys, right? She knew that at some base level, they couldn't believe that she was that fucking much better than they were. She was just, oh, I'm just little Annie. I just don't, oh, what am I doing? Right? And she just smoked all of them because she was a world-class player. And so what she was really good at with Ben was teaching him how to use his kind of celebrity the same way in those games right you get in those games and people are like it's fucking ben affleck what

does he know yeah right it's a fucking actor right meanwhile he's a fucking assassin yeah and you just lost 20 grand to him right like a wall street person right and then and then there's the wall street there are people just like i don't care i just want to be in a hand with Ben Affleck. But so those games, those cash games, I think got crazy. And I think Toby, you know, Toby's like, by all accounts, I mean, you know, by all accounts, he is like a world-class poker player. Maybe that's the plot for Rounders 2. Mike McD is in a blood feud with Toby McGuire, but it's the real Toby McGuire. It's actually Toby McGuire. I thought you were just going to suggest Toby plays Mike McD, which would blood feud with Tobey Maguire, but it's a real Tobey Maguire. It's actually Tobey Maguire. I thought you were just going to suggest

Tobey plays Mike McD, which would actually be good too. No, it's like a being John Malkovich thing where he's actually in the movie as Tobey Maguire. Or when Julia Roberts was in Ocean's 12 as herself. Right, right. That could be good. I think we came up with it.

Matt Damon, this was fun. Thank you. Thank you guys. Appreciate it. All right. Thanks again to Matt Damon. Thanks to ZipRecruiter. Don't forget to go to was fun. Thank you. Thank you guys. Appreciate it. All right. Thanks again to Matt Damon. Thanks to ZipRecruiter. Don't forget to go to

ZipRecruiter.com slash BS. Thanks to TheRinger.com. Check out all of our awesome NBA preview stuff that we have going. Season's starting soon. Check out TheRinger Podcast Network.

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