Fly on the Wall with Dana Carvey and David Spade - Charlie Sheen Bets On Himself And Keeps WINNING!

Episode Date: October 2, 2025

Dana and David welcome Charlie Sheen (and brother Emilio Estevez briefly). Charlie relives sitting shoulder-to-shoulder at Canelo vs. Crawford with David (and living to tell it), deconstructs the origin story of his most famous catchphrases, and shares what it was like growing up alongside Rob Lowe and Sean Penn. Charlie breaks down the legendary 10–90 deal where he bet on himself and WON, the blockbuster roles he passed on, his surprising memorabilia obsession, and the moment he was convinced Tom Cruise was Latin.  Prime Members, shop deals up to 40% off this Prime Big Deal Days, October 7th and 8th! To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

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It was, it was, it was, it was, it was, it was, it was, warlock or bust. Yeah. And I said to Dave, I said, if that, if that breaks loose, we're clearly in, in the crush zone, right? And I said, are you cool if I'm the last guy, like on this planet that you interact with? Charlie Sheen. Charlie Sheen, the one on known. Internationally known. As God is My Witness.

I don't know what that means. You need a witness for that? It's just a figure speech. Charlie Sheen. What a career. Yeah. Huge movies. You were talking about his run of movies, like, from 21 years old, I think he popped in a Ferris Bueller with a cameo, just a good-looking burnout dude.

Did one scene and stood out. Yeah. I think he stayed up all night for that to show that he was a guy that stayed up all night. Yes. And when you're 19, you stay up all night. It's not a massive difference. It's not a big deal. He's wasted.

Yeah. But I guess he, I think with Charlie, when he went off the rails a little bit, was. too much fame, too good-looking, and too rich. It's just you get everything you want. It's a very odd. I don't know the feeling. It's very odd. Being medium-rich, medium-looking, and medium-ness across the world.

It's different. So he just has everything. All girls are falling at his feet, and he's got drugs wherever he goes, and every celebrity wants to hang out with him. Yeah. Huge movie star, he's 21. He's doing Wall Street. It really is kind of unparalleled how many movies he's made.

And platoon. At such a young age. Yeah. And then he got into all the funny movies, you know. Hot shots. Hot shots, yeah. Major league. There's like so many to talk about it.

And then he does this massive sitcom, two and a half men. One of the last ones of that kind of big audience. Big audience. syndicated fat money and then he really and there's no real limits he doesn't care what we ask him and he was pretty funny we were light and loose with them and we couldn't do it in person because I think all of us were sick remember right I was I was full COVID yeah yeah I enjoyed this one a lot with Charlie Sheen I found him really charming I know he's had a lot of rough times in his life but the guy I met on the Zoom is a real charming, humble, nice guy.

Yeah. And funny, too. You decide, folks. Here he is. You decide and give us your comments. Here comes. Here. Hey, what song is this, Charlie?

What song? Here he comes again. Looking bad. What is that? Dolly. My body has a right to. I don't recognize it. Here he comes again.

All right. So our producer said, Here he comes, so I just stuff up to my head. Yeah, I think we're good. Awesome. Thank you, bro. Thank you. Charlie, this is a great place if you're a termite.

That's Emilio Estabez right there. Can he hang out for a second? Because that was my first thing I wanted to talk about. They're asking for you, dude. Emilio, you won't remember me. You mind? This was one of my things because I wanted to not bore the shit out of you. Emilio, I just want to.

You're in my research. I'm not making this up. I was like, because I was like, holy shit, I saw the doc, I saw you guys doing all little super eights and all that. And then you're fucking, you do, you got, there's Red Dawn, but you do platoon, Ferris Bueller, Wall Street, Major League. Your brother does the outsiders, repo man, which is a personal favorite, breakfast clubs, and then you connect with young guns.

So what the fuck? That has never happened in history. you both were like children, little tiny kids becoming movie stars like that. Anyway, that's why Amelia, we just want to tell you, you're a fucking stud. Yeah, I mean, you guys are like, he can't hear you because I'm on the, I'm on the, on the, oh my God, we tell him we gave him a hundred compliments and now he gave you a hundred compliments. And it was all love and it was about the breadth of our, of our combined films in that, in that time frame. And he said, then we did all that.

movie stars as children yeah so we were all we were all the same when i was a waiter till i was 24 would he tell him that he said he was a waiter till he was 24 yeah it wasn't in that boat wasn't in that boat um anyway all right amelio so we can't hear you but nice to see you buddy thank you bro thank you i appreciate it's great to see it that's cool that's that's cool that's a treat But seriously, that was most of your time, Charlie. That was most of our time. We look better in person. Don't think of this, what you're seeing now.

We're pretty good looking, David and I, you know. I just saw Charlie at the fight. Yeah, that was pretty cool, wasn't it? You know what? Let me tell Dana, the funniest thing you said is right when I said, Michael Irvin had his legs wrapped around your chair talking to someone behind him. And you go, I don't think Michael Irwin knows spatial awareness. I mean, it was an astute observation, wasn't it?

It was perfect because the chairs were this wide. Right. They were little plastic chairs. I go, Ted, Serendos is in front of you. I was like, Ted, I want to talk to you about the shitty chairs when you get one second. It's too late now, but maybe for the next one. And they were all tied together with zip lines. They were zip tied together.

Yeah. Yeah. Well, spatial awareness is a funny word. It's a funny term. What you're doing, Charlie, when it comes to comedy. That was funny. You could have said in a lot of different ways. But facial awareness, because we're stand-ups.

You know, that's all we do. So, well, he's a film star, but, yeah, you're a comedian, you know, just, I was looking into some of your rants. We can go wherever you want, but they're all really fucking funny. That's what really struck me about that era of Tiger Blood and everything. I mean, they're comedically like, I'm sure other people are. It's actually funny on top of everything else. It's not the rantings of a madman.

It's a comedian unleashed. you know yeah wow okay i've i've never heard it uh described as such that's uh are you on drugs yes i'm on a drug it's called charlie sheen that's like rhythmic and and how are you doing winning not just i'm winning these jokes are to like katie kirk are this the most flat audience savanna guthrie going uh-huh you have a bit a lot of problems in your life you're like or do i i'm on coke and they're like well you're laying down imagine You didn't even know at the time because the whole idea, which I think in therapy, they should use these quotes because they're funny and they're self-affirming. They're kind of saying, fuck you, get out of my way.

We all want to have that feeling sometimes, but I looked at them as the work of a comedian. I mean, they're just really, are you bipolar? I'm by winning. I win here. I win there. Now what? This is funny. They picked a fight with a warlock, you know.

I mean, it's just funny. I don't know if anyone is, we're trying to think of stuff that you haven't been asked, because I know this is our second interview around the book of Sheen. You've done one interview and then this. And then this. Yeah. So we wanted to surprise you, but there are things I wanted to talk about. That's one of them.

But David, can you have any questions? Go ahead. Charlie has a quick question. Charlie. I just want to point something out. If I say you've picked a fight with a warlock, right? that's like that that implies that that that implies that I would have experience with that that or I'd have some kind of yeah perspective or context with that right I've never

picked the fight with a warlock no I think that's kind of a just a life rule that that that you don't you see a warlock you don't pick a fight you know no and we all know I don't even know specifically what my image is but warlock kind of means like some sort of weird mythological creature you don't want to go near exactly exactly did you have did you have any alt you did you have an alternative to warlock or what happens just boom they picked it it was it just comes out warlock or bust yeah he's got the phrases that are very catchy but no one has ever heard do you own these though they're all over online they're so funny charlie part of it is when you're in these interviews and i watch these people with a lot of it unfortunately is fake

concern for you you know what i mean they're like hey are you okay and you're like what do you give a shit. Do you really care? You're like, are you calling the kids every night? You're like, do you want to babysit my kid? At a certain point, you start to go, are you really, really, if you really care, I'll tell you these answers, but you're kind of trying to get a pickup piece for your clip for the news or for your show. And so you're using me to go, oh, I'm going to be the concerned person condescendingly asking Charlie. You're like, I have $100 million. Is it horrible right now and that's that's kind of a weird place to be in where they're like do we envy you or do we feel sorry you know because you had a lot going yeah no but but but when somebody poses those questions um

what do you think would have happened if i had said um i'm i'm not and how how do you uh plan on helping yeah what are you doing like do you have a guest room do you have uh yeah do you have a stocked fridge. Yes, they're crudette anywhere that I could have access. Right? Yeah. So it's like Facebook moms putting on Facebook. I don't like when you showed a picture of your kid in the front seat.

You should never like, what do you care? Are you really, you really that worried? Anyway, we got so much to talk to Charlie about. I also want to just insert one thing on winning and also the way you said winning. Winning, you know, did that influence Trump kind of? Because he really works a word and he really, you're going to be winning so much, you're going to win, you win. I don't know. There is something about that word.

Did you win? Yeah, I'm winning. I'm winning more. You know, I don't know. It's just interesting interaction historically, but who knows? Right, but the book gets into the genesis of that material. Oh, that's what I'm, I'm so happy to hear, the book of Sheen. Yeah.

Thank you. And it's, you know, I kind of kept it, it kept. kept it a secret for years that it wasn't my original material, that it was inserted into my brain sort of as a pep talk like a couple days earlier by a baseball player from the giants named Brian Wilson, a guy nicknamed the beard. Remember the beard? Oh yeah. Yeah. So yeah, I was watching a highlight package of his and I told my pal Tony Todd. I said, hey, I'm going to talk to that dude. And the next day I was on the phone and he just rolled out all all that stuff, the stuff that the material that turned into slogans and t-shirts and folk songs and everything

else right and so yeah but then i couldn't really say in the middle of that that that that that that whole you know tsunami that i was cresting on a nuclear surfboard right i couldn't i couldn't say by the way all that shit was borrowed that t-shirt you're wearing not my stuff i just had to roll with it and then about midway through the all the chaos i spoke to him and i said hey man i'm sorry I feel like I stole your stuff and maybe you had plans to use it elsewhere. And he said, no, no, no, it's fine. I said, and you're probably thinking that you got it into the wrong brain and hence the wrong mouth. And he was like, well, you know, it's, I never quite saw it going this far.

But if someone's going to borrow your material, then spread the love. Why not? Well, yeah, because it was the timing and the way you delivered it. And it's you saying it on all over the place. It's you saying it in the rhythm. I don't know if he was, because that was your rhythm, right, of the way, you know. The winning thing was originally delivered with that inflection. With the high pitch to winning.

Winning. Yeah. Yeah. I know. And that's why it got, it got, you know, logged in there like that. So his material, but then I think through my filters and, you know, through whatever else was going on, it became. what it did, you know. Right, because he was being interviewed sometimes by contrarians or whatever

trying to talk to you and you were just coming back with something so extremely different than anyone would expect that that was part of the comedy of it. I don't know if he had people interviewing him, you know, in that way. But it's interesting. Also, losing isn't quite as catchy. It doesn't. Losing. It really isn't.

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Oh, go ahead. You got one question. Go ahead. He can talk too, though. You can talk whenever you want. Thank you. Have you and I ever met, Dana? I don't think we've ever met.

I don't think so either. No, I don't think so either. We almost, Fred Wolf was doing some kind of movie and you were in it and so I didn't do it. Yeah, mad families. Yeah. And I was for a while I was going to do that, but I just was doing stand-up or whatever I was doing. But we would have met then. Yes.

Yeah. And David and I had a scene together. Do you remember this? Oh, that's right. And Matt families. Yeah. Do you remember I like rewrote it and I turned it in like three pages and I came you like five minutes before we were going to shoot it.

I'm like, let's do it this way, man. I was fucking hammered, dude. I was hammered that day. And apologies. No. But we did have a nice vibe and a nice rhythm and a nice thing in that scene, didn't we? Yes. I remember that was, Naya Rivera was in that movie.

Little, was a little rel in it? Little rel, yeah. Little rel. And yeah, I do remember coming to do one scene and I had to, to speak with everybody. I don't remember enough about it, but if we did a collab that I hope it came on,

right, Mad Family sort of was, we call it under the radar because it was on crackle. It was on crackle. Yes. Crackle turned into an app. It was supposed to be like Netflix

and then it kind of wasn't. It sounded like Norton. Very much. It kind of wasn't. Yeah, they kind of bailed on it. You know, Charlie, do you remember the story of Tom, hurts try to put a show together with us and it was after you left two and

half men okay Tom Hertz and all his wisdom was working on two and a half men for years I guess then he came to do rules of engagement another show that I did no Tom Tom Tom was on Spin City I think also Spins oh spin City and then he came to us because yeah worked with you and he knew you sure and then and then he came to me and said what about you and Charlie doing a show and I said isn't Charlie a little bit

in the dog with the CBS because it was literally in the middle of all that and he says well Les Moonvez likes this idea I was like he does

even in the middle of Charles I think either you guys were suing each other there's some pure chaos obviously and I was like well and then it kind of fizzled out but I thought it would have been fun back then that was a it would have been kind of a fun

pairing. Yeah. So it, no, it would have been awesome. And so it would have been that instead of anger management, right? Oh, yeah, maybe. Yeah. That's what you went into next. Oh, yeah. Was an anger management was a 90-10 deal? It was 10-90, yeah. Yeah. Those are those deals, Dana, where you would shoot, it was sort of a new formula where you'd shoot 10 episodes and if they liked it, they'd buy the back 90. So it's very interesting because you'd gamble. And Charlie Gamble and won again. And he got a hundred out of it, right? Yeah, we got to 100, but it didn't, it didn't catch fire like we were kind of hoping, you know?

Sure. But it's interesting. It's literally like a 10-episode pilot. Yeah. And so then they take the average number from those episodes that air, and it has to get above a certain threshold. And if that happens, then it activates the next 90. Yeah, so you get a piece of 90... You get 100 episodes and you get back end on it or participation.

Exactly. Yeah, you take a lot less upfront salary, but you have an ownership position that's pretty significant when they work. But this one, because I wasn't, I wasn't ready to go back to work, you know. Was it right after two and a half men, so it's hard to like go right to a show? It was about six months after. Yeah, that's pretty fast. Yeah, yeah, which for me probably felt like a weekend, you know, at the time in the middle of all that, yeah. And Dana, you wouldn't like it.

It's like two in a day. Don't you shoot like you shoot faster? Yeah, and there's no audience. And sometimes you're doing two shows a week or you didn't finish the second show from last week. So you start the week with that. So you're really trying to focus on three shows that week. And it's just and it doesn't.

Yeah. I think a lot of the process suffers, you know. Not the thing to get you off drugs, that's for sure. Definitely not. No. No. Certainly not. Most of the casts end up on drugs when they do the 10-90 thing.

I'm sure. Because of the pressure. I heard of my friend, a friend of mine that we all know just did a 10-90 deal or 90-10, whatever we call it. And I don't think it kicked in. So it's the gamble. You know, you're betting on yourself. And I think it's a pretty good gamble.

I probably would have done one of those because it's something. You get some money, but there's a big high reward. Sure. Wait, your friend did one recently? Recently. That's what I had heard. Oh, it's still going on. Are they still kicking those around?

Wow. Because I thought they kind of went away. Was it a multi? I'm pretty sure it would have been a multi. That's probably the fastest you can do it. Yeah. Okay. You know, I'll tell you after, but I don't want to say anything about his real name because

maybe he would feel like, oh, didn't get picked up, but I'll tell you after. And that's very interesting, though, that the 10-90 could still be floating out there. When syndication isn't quite as valuable, obviously, you were sort of one of the last, not the last, but you, your show, two and a half minute, which is still on, you know, honestly, too much. And it's on probably 12 stations at any given time. When was the end? I mean, it was that when the syndication thing started to slowly die. Big Bang was one of the biggest ending.

yeah sure yeah he had modern family you know when when when was it on as far as like when was it like actual broadcast yeah the block when syndication was a really big thing still you know because that was Seinfeld the 90s and so forth but I guess it got that pop and you were making a really good a good salary yeah you know um I mean I was I was trying to negotiate my way out of it I was I was waiting for them to say, it's, you know, all right, we're done. Seven is plenty. This guy's asking for the moon. We can only afford.

The only guy in America trying to get himself out of like a huge show. So by asking for so much money to get out, basically? Yeah, I was calling their bluffs. And then they said yes. Okay. They said yes. I was like because I had a conversation with my manager when I was in rehab, when they were trying to negotiate for eight and nine.

And I felt like seven had just, I kind of just. reached my limit. I didn't see that we had a lot of stories left to tell, you know, and I just, I'd completely lost a passion. Tons of, tons of shit in the background in my personal life that wasn't, you know, I'm not blaming anyone, but it was making the job just more complicated than it had to be, you know, and, and I told, I told my manager, Mark, at the time, I said, if I, if I go back, I have a hunch that something is going to go, it's going to go horrible. The dam's going to break. The dam's going to break. Yeah, man.

Now, do you think that was a self-fulfilling prophecy? Or do you think I just knew that that's how the planets were going to be misaligned? Well, I think you know when you get overwhelmed. I think you know, I mean, everyone says money is the key thing. But when you already have money, you've been rich probably since Apocalypse now. You've had money. A couple of beans in your jeans. All right.

Not Apocalypse now, Platoon. Red Dawn, he got back end on Red, Red Dawn. Yeah, it was over. It's still paying. Yeah. Red Dawn covers those hunts. to accord payments, just alone. So you got that, and then you go,

everyone's, your life is great with money, but it sounds stupid, but it does complicate a lot of things, and you've got so many complications going on. And I think you had a trailer on the set, as opposed to addressing them. Did you have a bus or something? I had a tour. I had a tour bus. A tour bus. That's what I had heard.

Yeah. I was jealous when I heard. I had a marathon coach. It was pretty cool. Right outside the stage door, probably, right? Like, we walk out and then, yeah, it was, You shoot. It was right there. Yeah, you shoot, you go in and wait, and then you come back in and do your scenes.

So you can do whatever you want in there, obviously, and probably took advantage of that. Two and a half, not so much. The stuff before it and the stuff after it very, very much so much. Yeah. When did you first feel like incredibly wealthy? Was it after Wall Street or for you, you know, you're in your early 20s. when did you kind of go holy shit i'm a millionaire or i'm close to a millionaire you know teddy stuff right it was probably like in like mid 90s okay yeah but there was about 30 yeah yeah

but there was a moment early on when i got my first uh acting paycheck from grizzly from grizzly to the predator oh or the revenge as they retitled the movie grizzly they did a sequel yes yes yeah and so I made two grand a week and I was there for three I made six grand I didn't care I didn't know about taxes or any of that shit and I went to the bank and just took it all in cash and I walked into a clothing store and there were these two kind of fancy uh vests not like a western vest but like a like a camping vest right and I couldn't decide on the color it was like a blue one or a freaking green one and I was like I'm going to take them both whoa yeah and they were like you know 40 bucks each, 60 bucks each, whatever, and just laid out the cash. And literally in that moment,

I felt, okay, all right, this is, I'm feeling like a big shot. Sure. And I think you all take both. And then you go, you like that shit. And the lady goes, oh, there's more where that came from, bitch. Why are you being aggressive? I don't know, bitch. Maybe it's the money winning. How old are you? I hate to interrupt. I did a police academy movie and I was making not much money, but it was no more than I ever had in my life. And I saw some pants in the window in Toronto. And I went in and the lady goes, those are $60. It was like pretty woman. Like those are for rich people. And I go, I'll take them. And she's like, whoa. Everyone's store was like, whoa. And I was like, 60s, nothing to me. Because I got $100 in pretty him. So I bought it. I literally, there's very few

times I felt richer. We all have that story. You know, I was interesting. I'm sure this, in the book that you'd think, hey, Martin Sheens' his dad, he's growing up like a billionaire, you know? And obviously in the documentary, it's, it's, it's, it's pretty middle class, you know, it's not fancy pants. You and Emily, you guys didn't have money. Go ahead. You can see our house in the background of a lot of the Super 8th stuff, you know, and it's not a mansion. Documentary. It's not a, not a manicured freaking no, no, it's very, it's funky and cool, great for a kid. But I was wondering if anyone in that posse,

like I'm fascinated by Sean Penn and... Sean, when did you meet Sean? And Rob Lowe or are your friends? Did anyone have a Silver Spoon? Or you're all kind of middle class in a sense. We were all middle class. Rob's... The Lowe's came in a little later.

And the reason, you know, he wasn't excluded intentionally, but the footage that the director, Andrew Renzi, chose to incorporate was from you know the like the younger younger years you know I think by the time I started making those films with with Rob and his brother Chad

I think that I think video videotape came into play it was actually do you remember this thing called the it was like a Polaroid brand but it was a Polaroid video camera do you remember this? I never heard it literally it developed

in the player while you were waiting and then it played it um it was it called polar vision i think so that's you know yeah so we were sort of in the cutting edge of like as the technology was improving um but no his his his the low's uh dad um was was still in ohio and their stepdad was a psychiatrist They lived right down the street. Sean's parents, a director, actress. You know, they were married until the day they both died. And so, but nobody was, nobody was rolling.

Nobody was driving a fancy car or fancy duds or, you know, picking up a check. So, yeah, it was, it was really a cool time to just experience all of that and not have a ton of excess and special effects and bullshit sort of in the way of of of of those memories you know and super eight or whatever that was is so it's just emotional you know and and i i think it's funny like every kid who ever got a whole of a camcorder or whatever they always want to do war scenes or crime scenes and want to do a death scene like ah sure did you have a good go-to move like oh um yeah the platoon move is a big one Will and Defoe? Oh, yeah, the whole, yeah.

The crucifixion. That's been reenacted all over. Yeah. I actually, I have that as a sticker in my phone that I send people. When I know how to respond, it's just Defoe. It's like that. So if you get that, it just means I'm stumped, you know? Fucking send me that.

It is interesting of like the trifecta. I think you, for Vietnam War films, you know, you'd say Deer Hunter, Platoon, apocalypse now and there was a sheen in two of them and i think that that film really along with wall street and others really holds up you know platoon has has some magic to it and would you put would you put full metal jacket in there anywhere or no i put anything kubrick does is a given yes yes i would that's a good call full metal jacket anything kubrick pretty much you know sure is just magic. You know,

Poplux now, brilliant. Masterpiece. And Dear Hunter, you know, the MOW! Oh, you know,

with Christopher Walkin, one of the greatest most intense scenes ever made. So, yeah. But you're part of that and it's pretty cool. Thank you.

Thank you. Charlie, what movies did you turn down that sting the most? And I'll tell you which one. If it's opportunity, Knox, I'm so sorry.

If it's Tommy boy, I'm going to be me. I'm so sorry. It's between you and me. No, go ahead. I turned down white men can't jump. Were you going to be Woody or West? I would have been Woody, yeah.

And then just coincidentally, a bit later on, I think it came after, maybe before, I turned down indecent proposal. Whoa. So I kept waiting for Woody to send me some flowers and thank me for advancing his career. like I did. Those were big. I found Indecent proposal, you know,

I'm a huge Redford fan. God rest of all. And to me more and everything. But I just found the movie very depressing. Woody's character was so like, I mean, that was the only thing

I'd say about Dodge. I don't know. It just wasn't my favorite movie, although it's skillfully brilliantly done. I just was like, you know. I couldn't get past the thing

that, all right, they did that. He's got the money to, you know, to lessen this thing a little bit. Yeah. And then Spence

it all on that chotchky right right like the little jade elephant or something ever yeah yeah am i misremembering that um no it was something weird it was a very it wasn't love was real and it wasn't about money and it wasn't about this but they still have to stay married and live with that moment right with the thing with thread which is tough right yeah you don't get much wrote back charlie's agent wrote back charlie likes it uh but wants to tweak the ending pretty much and they said it's We're pretty locked in the ending. He said, that's a pass from Charlie. That's pretty much how much how we're going on.

Did you see Brokeback Mountain and call your agent? Why the fuck wasn't I up for this? I have to admit, it's kind of one of those films that's always been on that unseen but need to get to at list, you know, and I think that we all sort of have. Yeah. So I never saw it, but I hear it's fabulous. Well, it's, yeah, it's, it's a little heartbreaking. but yeah the performances are exceptional you know sure yeah uh good fellas good fellas we're up for

that i was not up for good fellas no karate kid uh karate kid is is one that um that i actually had um i don't know if i could um classify it as turning it down or describe it as turning it down it's um I just, I, I, you know, it's in the book, it's in the dock, I think, and that I, I just asked for some time because the advice from my dad was to, was to stay, to honor my word with Grizzly. And, because I'd already, you know, committed to that. Fucking Grizzly comes into the picture. That fucking bear, that bear ate me twice, right? Jaws on land.

Grizzly. So he said, um, if, If they wait for you, it's meant to be, if they don't, then it's your, you know, your reputation being a man of your word is going to carry you further than one big movie. From afar, I do have a lot of admiration for your dad. I did meet him and I did something with him one time. It was just a charity event. We were all doing Shakespeare with Tom Hanks, but that's good.

Yeah, well, it was kind of like pretend fun Shakespeare. Was it in the park? They do that in the suburbs. Anamanican in theater. It's a reading, right? Isn't it a reading? Yeah, but then we all go on stage and sort of get around in our reading. You know, I'm doing impressions and things and that's Shakespeare, you know, one thing I was

going to ask is people of people who've been in brilliant films around brilliant people. The, you know, you've been across your partner, man, or a woman and went, damn, you know, this person is exceptional or someone who kind of took you back a little bit by just how great if they were at this thing called acting. Sure. Who might those people like that? I wanted to bring up the elevator scene with your dad. That was one of those moments.

When you actually get distracted because you've become an audience member. And then wait, but you're in the scene. And shit, it's my line. You know what I mean? It's like those moments. And I had some of them with Michael Douglas on the same movie. Definitely had him, definitely had him with dad. even though he's only in it, you know, just a little bit.

James Spader in Wall Street. I was kind of like going, oh, shit. So they're doing it like that now. You know what I'm saying? It's like this whole thing. And then, yeah, it, who else? Who else? Oh, shit.

Michael J. Fox. Yeah. When we had a couple, we had a couple scenes together. He had transitioned out and I had stepped in. But he wanted to stay close enough. it to like to bridge the the transition you know and yeah and yeah we we we did some scenes together and it was it was other level talent i was like he's out i mean you look at back to you take a look at it back to the future i'm doing trump but uh that's hard to do you know and i know he replaced

eric stoltz who probably was great but to be light play it dramatic and and ride that whole wave of those movies yeah michael j foxes i don't know if he's underrated or a appropriately appreciated. That's a great question. But it's interesting because there's a thing that I do describe in the book and it's it's it's really there for a reason, you know, not just to celebrate and honor him, but also because that's like that's my last outpost before going on to two and a half. So I was kind of symbolically implying like, okay, I borrowed a little bit from this dude, you know, because there was tons flying off of him and took it over to that thing. And and we know we saw how that thing went, you know, so...

Well, it's rare. Can you imagine how excited when they get two and a half men together and Chuck Lorry and the cast is there? And then you're just, you're winning, you're killing it. Like, because it is a skill set and you started in Spin City, but then it's hard to find a leading man, handsome leading man, who could also be very funny, you know? So they must have been, you know, high-fiving at some point. behind the scenes like you know just just because you're you're you're great at this too you know thank you thank you um but it was all it was just playing the straight man you know and when i did it in the hot shots you know but yeah i and send some of that shots that's right well when i did

it in hot shots i was i was borrowing you know a lot of stuff from lesley nielsen yeah you know who better to borrow that was the theme of that was sort of the feel love that movie hot shots oh thank you Thank you. And then I was borrowing stuff from Ted Danson on Cheers for two and a half. But I know he's a sober bartender and I was a drunk jingle writer, but just as far as the straight man. And you know what I'm saying? He's he's kind of the anchor and all the all the craziness revolves around, you know, orbits his star, his planet. But you're not putting huge spin and overacting.

You're not like Kramer. You know what I mean? You're just saying your lines and they sell themselves with good writing and they know how to write for you and you're just. It's hard to be a funny straight man like Andy Griffith was to. Right. Right. Right. Right. But thank you. That's, but especially coming from you guys, come on, two, you know, veterans and, you know, extremely successful veterans to get comedic compliments from you guys is really badass. So thank you. think well don't you and your and your own personal life you know kind of fall in love with talent um you know it's just kind of fun to watch you know and i and i was this was maybe a clumsy thing but you know i thought of people would get out fast you know and it's it's a rare but it's kind of that are very talented like well i'm talking about woody allen and i'm talking about the beetles

bob dillon you know by 21 22 brando and you were kind of in in that group in a way i'm just saying loosely because you came out so good and showed so much talent but you know who it musically who's your who's your north star like when you the canon of rock and roll are you pink floyd or are you are you Neil young or lead lead zeppelin well i just watched that documentary on the plane they were pretty good yeah yeah i think they got a shot that's probably legendary frontman Led Zeppelin. Yeah. What'd you think of the dock? Did you like it? I thought it was pretty good. You know, I always like when it gets to more, I don't always like the beginning. I like to know just to where I knew them, you know. But it was very interesting and everyone loved it. So I watched it in the

plane, it was perfect. I ate it up very quickly. Yeah. Yeah, it's excellent. What was your thoughts? I love playing. I would have liked that they got to if they'd taken it to Zep 4. Right. It could have gone longer. Yeah. Yeah. Yeah. Because that's the one. Because they only started to get of the stuff I really liked and I was like wait is that it it's over I was like go go go go yeah we're landing that's true it was interesting for a doc to show them I guess it was on a TV show or somewhere but you showed them really jam for like 12 minutes or something like really go song I think they showed one full song I think it was rock and roll they showed the whole I think you're right yeah and I was like this is the one is probably I mean as good as any

oh question Charlie you collect things and I'm sort of in your orbit we're roughly the same age roughly in showbiz you're you're obviously doing a ton of stuff way more but in a weird way i remember i'd heard i was at an elvis auction at butterfield and butterfield in the old days i sometimes buy collectibles and shit i think you're in a maybe baseball card so i always heard that and was there an elvis green amex you bought ever because i think I had my eye on one of those. Wow. And he said,

I think Charlie Sheen got it for 50,000. That's the kind of rumor that you want to embrace. That's a cool one. That's pretty cool. Because then when the bill comes, everybody's kind of waiting for you to drop that thing. You can buy. That's too cool.

Dana, I bought an Elvis set list, you know, like he wrote on some Michigan Hilton. He was writing all the songs like Love Me Tender, his handwriting and shit. Oh, wow. And so I bought that and I bought a gunny,

had and I bought something else, but I wanted this Amex, but it was too rich for my blood and that. What did it? Because I didn't buy it. This is the first I'm hearing about this Elvis auction. It sounds awesome. How much did the Amex go for? 50,000. 50,000. And that was 20 years ago. Wow. Because I was at the auction and Joey Esposito was there. So they were like authenticating stuff. And I bought a watch. And I don't have, I don't think, anything left from that because I lost the set list. But I bought stuff before and I thought, oh, I think Charlie does maybe baseball cards or just, or maybe baseballs, I don't know, but.

Yeah, I got, are you in and out of that biz or not? I've sold everything. Okay. And, and I should have come to that garage sale. Jesus Christ. What did you, what did you sell that was a little bit like? I had, I, geez, I had something like from every era. I had a lot of Babe Ruth stuff.

I had that famous long white overcoat that he's seen in tons of photos. Oh, had the coat? Oh, you had the coat? Yeah, I had the coat. I mean, there's probably more than one, but I had one of three probably. I had a lot of jerseys, had a lot of caps, a lot of hats, some great bats. But there was a turning point moment where, because I had these cool cases built at my house up in Malibu Lake years ago. and I had been to the Hall of Fame for the first time.

And I thought kind of, this is back then like in 1991. And I thought what they had, how they had set it up was a bit shoddy. I thought this stuff. I could see like a moth like down in the corner behind the glass. And I was like, what are they doing? Right. Right. Yeah.

And so I, I was inspired by it. I wanted my cases in my house to be like nicer than the Hall of Fame in Cooperstown. Right. And so we brought in the right people and, you know, And they delivered that, right? But then a couple years later, I was looking for something. I opened a dresser drawer up in my bedroom. And there's a 1941 Ted Williams Road jersey, like just folded nicely and in the drawer.

Wow. And I had that, you know, it's the area hit, you know, 406 and all that. And I had that moment of if I don't have room on a wall for this, like this is the last time that anybody ever did the thing he did while wearing that, then I need to recirculate a lot of these artifacts and antiques and just let others enjoy them. And then I, Leland's put together an auction. And it was all sent back out in the world, you know?

Interesting. And some cards are not a Honest Wagner card or was it. I had one called like the five pinhole card because they're so graded, so anally and they have to describe everything and I guess I guess some kid back in the 20s like was sticking it up on a on a on a board or somewhere in his bedroom oh and it was holes in it yeah but don't you think you at least you just keep using the same hole why did he have to make five holes um no those dipshits they're ruining cards for the future I don't know yeah they really were so but I'm sure that went a little pricey yeah yeah it was it was up there but not

nearly when that Wagner card really got everyone's attention. When Gratzky partnered with, was it McNall, gun named McNall? And they paid like, what did they pay for that? Like 500 grand? Everybody was like, this is out of control. And now you think about that. That's like chump change, right? Yeah.

I mean, all that stuff. It's one of the few niche places that just keeps going up faster than stocks. It's especially when people have a passion. and they collect their passion. And even, you know, Jay Leno probably has made more money. Or, you know, he won't sell his cars. No. But he probably, if he did, he made more money off his passion than he has his

comedic career. You know, it's very, I have a friend who collects antique bottles, and his collections worth $3 million. He's just dug them out of the San Francisco Bay because it was all landfill. And you go in there at night, I went with him, and you dig where they're excavated where you're digging down a hole. And then you see this little two inches. of ash. And that's 1906, the earthquake and the fire. Then you go further and you're pulling

out shoes and stuff. Once in a while, you get a bottle that's worth $50,000, you know, so it's interesting to further and you're in China. Yeah. You know, one thing I was going to ask Charlie about because I was seeing, you know, Cooperstown has this. I want to have more. And we all have this 10-year-old boy inside of us. And it's sometimes it's necessary to have success is just to have a fair play competitive instinct. They do that. I mean,

Nicholas Cage was so competitive. I did a movie with him, and we just made fun of the competition, you know, because Kurt Russell was in Tombstone, and he had a line in the movie. You're going to throw down, boy! If you remember the movie,

to Billy Bob Thornton, who weighed 220 pounds. So when Nicholas thought I did something good, you threw down, you really threw down today, you know. Wow. What film did you guys do? The films I do aren't even on video and they're banned from Earth.

No, it was trapped in paradise. Oh. We wandered around in the snow. We fell around in the snow, me, him and John Lovitz for three months and somehow they put something together. Okay. But Nicholas was a blast. He is, isn't he? One of the funniest and brightest guys I've ever met.

Was he one of your Malibu guys up there or no? No, it's not Nicholas Cage, your relationship with him. Yeah. no he's not a model guy um he was a town guy and a um and a and a bay area guy sort of back and forth you know i'm sorry what was the last question um well i i just wanted to know about your relationship with him you know because you guys kind of hung out i know there was you know extracurricular activities but just as a person i i found him very charming and he's he's one of my favorite people um i i we we don't see each other enough um but when we do it

It's, it's, it's, it's, it's, it's, it's, it's, it's, yeah, because you, did you talk about his intellect, you know, um, and then you wrap that inside of this, this, you know, outlandish sense of humor, just that is rooted somewhere outside of what, what, what us mortals can grasp. And it's, uh, it's, it's, it's, it's, it's an insane and beautiful mashup. He, he, he never saw acting as having to be accurate, you know, he just that found that you could do whatever you want it with it so he's doing a scene it's this cheesy movie and he's supposed to come in and kind of ask for forgiveness for this girlfriend or something like that and he goes i'm going to do daniel day louis from my father in this take so he comes all of a sudden he comes

out screaming falls to his knees why why why and i was like you can do that i mean he's a he's a unicorn i mean there's no rules with him there's no rules with him and and to have that kind of courage in inside that that those spaces is it's it's to be marveled at you know yeah he's oh i got something was tom cruz in or any of your early movies did you uh did you know he was going to be a big deal uh we knew yeah pretty soon because when chris sean's young brother Chris Penn dropped out of high school and bumrushed that set of taps on the other side of the country, he came back talking about this guy named Tom Cruise. In my mind, I added a Z and I thought he was Latin. I thought he was a Mexican or Spaniard or something, right? And then when I met him,

I was like, oh, you're from Oklahoma. And then he smiles. And then you start to engage his personality and his intellect. And you're like, yeah, this guy, this is, there's something going on here for sure. Emilio and he became really tight because they, um, they were, uh, auditioning for the outsiders at the same time and helping each other prepare for their auditions, you know, and then they both got it, the different roles. Um, and they've, they've, they've been great friends ever since. So I was, you know, I was younger than them. So I was kind of like tagging along. But, um, anytime I've, you know, seen Tom over the years, wherever, he's awesome. You know, Well, it's just become these last few years, it's like you sort of just stand back in awe, you know, because I'm basically a baby, you know, I may be hung from a wire once, but, you know, he's hanging on airplanes.

And I know like I'm strapped down. He's holding his breath for six minutes. I mean, you can't even, what the fuck? So you have to see the movie. What the fuck? Yeah. Yeah. Right?

Yeah. Yeah. Yeah. Do you think at some point he's going to want to get back to like a magnolia? Right. Right. Oh, yeah, that right, which was a work of art. And he was spectacular in that.

Yeah. What you got to respect the cock. I'm sorry, was that it? That was it. That's it. Yeah. Respect the cock. Yeah.

He said it better than I did. But yeah. He's a force of nature. It's funny because Sandler has the ability to go from a Paul Thomas Anderson movie to a big broad, and he goes back, Noah Baumback. Then he goes back to a broad. And I think Tom, obviously. he can do anything he wants but you're right these are important but mission impossible to top gun

it's huge huge blockbusters but what do you want to go small again would he want to go he could get an oscar he's great i think if christopher nolan called him or somebody like that you might even get his attention i think so i mean he does want to make movies that fill theaters and give people that that that that that experience that they that connects them back to their childhood that he's he's the savior of that he's i think he's made himself the guy, the spokesman. He and the filmmakers know this, but it was in Roman Holiday a long time ago,

but basically non-verbal with music. So the end of Top Gun, you have a six-minute montage of the end of the movie of people tearing up, no real dialogue and saluting, and we're alive and we did this. And I've seen other films do that F-1 and where there's this silent movie

added on to the movie, and it's very affecting. You know, that three or four minutes It's where you're seeing them in tears, looking at each other. And it's a lot of the blockbusters are using that now. So it's just kind of interesting to me. But Top Gun really got me emotionally because, you know, I hear Hans Zimmerman. I hear just the music.

I'm kind of, it gets me emotional. And then you see, Tom Cruise is really good at hugging someone coming back. He's got this look and the teary eyes in the kitchen. Yeah. Yeah. He insists that we experienced that moment with him. Right, right. Yeah. Now, is that the first top gun that you're referring to? Or is that, is this the second, second one. Got it, got it. Okay. Yeah. Which came out of nowhere was an in-movie theater big hit when the industry really needed it, obviously. But. And they tried to, they tried to stream it, didn't they? Well, he got on his watch. No. No. No.

He stuck to his young gun. Speaking of that in 1988. Thank God they didn't wait 30. between grizzlies. Right? I mean, that would have been a disaster, you know? This episode is brought to you by Peloton. A new era of fitness is here. Introducing the new Peloton Cross Training Tread Plus,

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What a run! This champ is picking up speed. Well, they found a lane. phenomenal launch into the air. Absolutely incredible Air Transit! Fly the seven-time world's best leisure airline champions, Air Transat. Shit, I think we're out of time, Dana. I think we had to wrap with Charlie Sheen.

Any wrap-up questions for this guy? Not really. I think the book is The Book of Sheen, the documentary. I mean, we consciously, we talked about it. We didn't want to, we know you've done a lot of press. We wanted to make this lighter and more fun and wanted to pick your book. about relationships with your dad or whoever sure no this is this has been incredibly refreshing um good that's what we wanted thank you and and if i'd like to believe that i get

invited back yeah that that'd be amazing and then we can do it like and be in the same room are you feeling okay with the thing that happened or oh yeah yeah i'm told okay i'm just okay just want to get one didn't want to give you anything but yeah no no and thank you i appreciate that but i do have a question for David. Yes. Good. And there was a weird moment during the fight, right? And as soon as I'm, you know, and Michael Irman, he's a lovely man. Yeah.

It's just beautifully all over the place. But what a good dude. But when I look over and I see Dave's name on the chair next to me, I was like, okay, all right. I'm going to have some backup. Reinforcement's coming in. I don't know why I thought that, right? Yeah. So he sits down and I'm like, did they plan this knowing that this was already scheduled, right?

Right. So they finally cut the chairs apart. Everybody's having a great time. And I look up and I see this giant rig, like where they had speakers and the lights and the thing weighs like, you know, 400,000 tons, right? And I said to Dave, I said, if that breaks loose, we're clearly in the crushing. zone, right? And I said, are you cool if I'm the last guy like on this planet that you interact with? And he took a beat, took a beat and said something to the effect of, yeah, yeah, I think I'm okay with that. And I said, good, because I'm okay with it being you too, you know.

And so I really bonded there. I felt like we bonded there, man. And clearly it didn't fall, but is that weird? No, but I like that you put that in my head. I think I was taking a beat because I was thinking, what of the, does he know something I don't? Is this going to fall? And then Marshawn Lynch sat in front of me and blocked 110% of the fight. Oh my gosh.

His head is this big? I go, wow. Wait, is the fight over? I go to watch on the screen now. Oh, I do that all the time. Can this fall or is this going to fly? Also, Dana, they show, they show, they show Michael J. Fox on the screen

and I go, for no reason, you can tell he's still mad at you, Charlie. That was funny. That was funny. Based on nothing. That was excellent. It was fun to be at the fight with Charlie. Laughing because I want you,

do you mind doing Michael J. Fox casualty of the war just for Charlie? Oh, me? If you don't mind. Remember that movie, Charlie? I do. I love Michael J. Fox. And Sean Penn is grabbing this. Yeah.

And he's like, Hey, Sarge, hey, you got to give me a minute on this here, Sarge. Oh, Christ, she's just a farm girl, Sarge. What are we doing here, exactly? That's amazing. It gets me every time. It's such an obscure, specific impression. Michael J. Fox in that movie, I was like, and Clarkie was John C. Riley and Sean

Ben's like, fucking Clarkie throw her down and take her clothes off. I'm like, hey, we've got to get these VC gooks. V.C. Gughor! I'm like, what is this movie? I thought it was a fun comedy because it was Michael's A. Fogg. Yeah. I'm like, this movie took a dark turn and never turned back. Yeah, they're just, and

whatever. And Sean, Sean was hard on him during that film, wasn't he? Oh, on Michael Zay Fox probably. I had heard about that. Yeah, yeah, yeah. Apparently he was just, you know, none of it didn't want to do anything. Because he's like you're a sitcom guy, kind of.

Maybe that, but also just the character. Oh, yeah, just a staggy character. Yeah, resentment, you know? Yeah. Yeah. It was the alpha alpha. Do you know, I've only, I've only worked with Sean in a, in a comedic setting. He was brilliant. It's, it was our first episode second season, and he's in a men's group. And it was Elvis Costello and Harry Dean Stanton and me and Bobby Cooper. It was awesome. But isn't that a trip that the first time he and I actually do it professionally? I thought he was. I thought he was. I thought he was. one-year-old movies. No, just the stuff you see in the dock where he shoots me in my own backyard and then stuffs me in the refrigerator for Emilio to discover later on. It was nuts, you know?

Yeah. He's grown He can be very funny though. I think he went on Friends. It was very funny. Such an interesting character. You know, SNL and he did the re-through, I go, wow, this guy's talented. Yeah, he's... Oh, right on. Right on. You know. Charlie, we'll do it again, and we'll do it. We've got more to talk to you

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