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Charlie Sheen Bets On Himself And Keeps WINNING!

October 02, 2025 / 01:01:20

This episode features Charlie Sheen discussing his career, personal experiences, and relationships with co-stars. Key topics include his early roles, the impact of fame, and his book, The Book of Sheen.

Charlie Sheen reflects on his rise to fame, starting with his cameo in Ferris Bueller's Day Off and his breakout role in Wall Street. He shares insights into his experiences on major films like Major League and his iconic sitcom, Two and a Half Men.

Sheen discusses the challenges of fame and wealth, noting how it affected his life and career. He humorously recounts his infamous rants and the public's perception of him during his turbulent times.

The conversation touches on his relationships with fellow actors, including Tom Cruise and Sean Penn, and the competitive nature of Hollywood. Sheen also shares anecdotes about his experiences on set and his thoughts on various films he turned down.

Throughout the episode, Sheen's charm and humor shine through, providing a candid look at his life in the spotlight and the lessons he has learned along the way.

TL;DR

Charlie Sheen discusses his career, fame, and personal anecdotes with humor and candor.

Video

00:00:00
He came back talking about this guy named Tom Cruz. Oh. In my mind, I added a Z and I thought he
00:00:06
was Latin. I thought he was a Mexican or Spaniard or something. Right. It was it was it was warlock or bust.
00:00:13
Yeah. Yeah. And I said to Dave, I said, "If that if that breaks loose, we're we're clearly
00:00:19
in in the crush zone, right?" And I said, "Are you cool if I'm the last guy
00:00:27
like on this planet that you interact with?"
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Charlie Sheen. Charlie Sheen, the one and only. Internationally known as God is my
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witness. Mhm. I don't know what that means. You need a witness for that. For what?
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That's God. It's just a figure speech. Charlie Sheen. What a career. Um, yeah.
00:00:51
Huge movies. You were talking about his run of movies like from 21 years old. I think he popped
00:00:56
into Ferris Buer with a cameo. Just a good-looking burnout dude. Did one scene and uh stood out.
00:01:04
Yeah. 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
00:01:11
night. It's not a massive. It's not a big deal. Yeah. He's wasted. Yeah. But I guess he uh I think with
00:01:19
Charlie when he went off the rails a little bit was too much fame, too
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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
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odd being medium rich, medium looking, and mediumness across the
00:01:37
different. So yeah, he just has everything. All girls are falling at his feet and he's got drugs wherever he goes and
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every celebrity wants to hang out with him. So yeah, huge uh movie star. He's 21. He's
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doing Wall Street. It really it's kind of unparalleled how many movies he's made
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such a young age and just Yeah. And then he got into all the funny movies, you know,
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Hot Shots. Hot Shots. Yeah. Major League. There's like so many to talk about.
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And then he does this massive sitcom, Two and a Half Men. one of the
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one of the last ones of that kind of of that kind of big audience syndicated
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fat money and then he he really and there's no real limits. He doesn't care what we ask
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him and he was pretty funny. We were light and loose with them and we couldn't do it in person cuz I
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think all of us were sick. Remember I was feeling great. I was full co.
00:02:39
Yeah. Yeah. I I enjoyed this one a lot with Charlie Sheen. I I found him really charming. I know he's had a lot of rough
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times in his life, but uh the guy I met on the Zoom is a real charming, humble,
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nice guy. Yeah. And funny, too. You decide, folks. Here it comes. You decide and give us your comments.
00:03:01
Here it comes. Here. Okay. What song is this, Charlie? What song? Here he comes again.
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Looking bad or what is that? Dolly body has a right to I I don't rec I don't recognize it.
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Dolly, here he comes again. All right. So, our producer said he here he comes. So, I
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just my head. Yeah, I think we're good. Awesome. Thank you, bro. Thank you, Charlie. This is a great place if you're
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a termite. That's Ailio Estz right there. Hey, can he hang out for a second? Cuz
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that was my first thing I wanted to talk about. They're asking for you, dude. Alio me.
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Do you mind? Why? This was one of my things because I wanted to not bore the [ __ ] out of you,
00:03:42
Milio. I just wanna you're in my research. I'm not making this up. I was like cuz I was like, "Holy [ __ ] I saw
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the doc. I saw you guys doing all the little Super Eights and all that." And then your [ __ ] you do you got there's
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red dawn but you do platoon ferris buler wall street major league your brother
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does the outsiders repo man which I is a personal favorite breakfast club almost
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fire and then you connect with young guns. So what the [ __ ] that has never happened
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in history you both were like children little tiny kids becoming movie stars
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like that. Anyway, I that's why Amelia, I wanted to We just want to tell you you're a [ __ ] stud.
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Yeah. I mean, you guys are they just he he he can't hear you because I'm on the on the boat.
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We tell him we gave him a hundred compliments and now he gave you 100 compliments and it was all love and it was about the bre the
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breadth of our of our combined films in that in that time frame. And he said, "Then we did all that. We're giant movie
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stars as children." Yeah. So, yeah. But we were all we were all in the same
00:04:53
We were all the same. I was a waiter till I was 24. Would he tell him that? He said he was a waiter till he was 24.
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Yeah, I wasn't in that boat. Wasn't in that boat. Um anyway.
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All right, Amelio. Sorry we can't hear you, but nice to see you, buddy. Thank you, bro. Thank you. I appreciate it.
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It's great to see him. That's cool. That's That's cool. That's a treat. But seriously,
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that was most of your time, Charlie. That was most of our time. We look better in person. Don't think of this
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what you're seeing now. We are We're pretty good-looking, David and I. You know,
00:05:27
I just saw Charlie at the fight. Yeah, that was pretty that was pretty cool, wasn't it?
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You know what? Let me tell you, I'll tell Dana the funniest thing you said is right when I said Michael Irvin had his
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legs wrapped around your chair talking to someone behind him and you go, I don't think Michael Irwin knows spatial
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awareness. I mean, it was it was it was an astute observation, wasn't it?
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It was perfect because the chairs were this wide, right? They were little plastic chairs. I go,
00:05:56
"Uh, Ted, surround us 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
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the next one." And uh they were all tied together, zip lines. They were zip tied together. Yeah.
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Yeah. Well, spatial awareness is a funny word by afraid. It's a funny what you're doing, Charlie,
00:06:13
when it comes to comedy. That was funny. You could have said it in a lot of different ways, but racial awareness
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because we're standups, you know, that's all we do. So, basically, well, he's a film star, but uh yeah, you're a
00:06:24
comedian. Um, you know, just I I was looking at some of your rants. We can go wherever you want, but they're all
00:06:30
really [ __ ] funny. That's what really struck me about that era of Tiger Blood and everything. I mean, they're they're
00:06:37
comedically like I'm sure other people funny on top of everything else. It's not the rantings of a madman. It's
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a comedian unleashed, you know. Yeah. Wow. Okay. I' I' I've never heard it
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described as such. That's uh Are you on drugs? Yes, I'm on a drug. It's called Charlie Sheen. That is
00:06:54
That's like rhythmic. And And how are you doing? Winning. Not just I'm
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winning. By the way, these jokes are to like Katie Kirk or just the most flat audience Savannah Guthrie going,
00:07:06
"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,
00:07:11
well, you're laying down magic. You didn't even know at the time cuz the the whole idea, which I think in therapy,
00:07:18
they should use these quotes cuz they're funny and they're self-affirming. They're kind of saying, "Fuck you. Get
00:07:24
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,
00:07:30
they're just really, are you bipolar? I'm by winning. I win
00:07:35
here. I win there. Now what? This is funny. They picked a fight with a warlock, you know. I mean, it's it's
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just funny. I don't know if anyone has I we're trying to think of stuff that you haven't been asked because I know this
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is your second interview around the book of Sheen. You've done one interview and then this.
00:07:55
Yeah. So, we wanted to surprise you, but there are things I wanted to talk about. That's one of them. But David, do you
00:08:02
have any questions? Go ahead. Charlie has a quick question. No, I just want to point something out. If I say, um, you've picked a fight with
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a warlock, right? That's like, um, that that that implies that I would have
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experience with that or I' I'd have some kind of perspective or context with that, right?
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I've never picked a 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
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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
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warlock kind of means like some sort of weird mythological creature. You don't want to go near.
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Exactly. Exactly. Did you have Did you have any alt? Did you had an alternative to warlock or was
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that was just boom, they pick them up. It just comes out. It was warlock or bust. Yeah.
00:08:50
He's got the phrases that are very catchy but no one has ever heard. Do you own these? No, they're all
00:08:56
online. They're so Charlie. Part of it is when you're in these interviews and I watch these people with a lot of it unfortunately is
00:09:04
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
00:09:09
[ __ ] Do you really care?" You're like, "Are you calling the kids every night?" You're like, "Do you want
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to babysit my" At a certain point, you start to go, "Are you really really?" If you really care, I'll tell you these
00:09:21
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
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using me to go, "Oh, I'm going to be the concerned person condescendingly asking
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Charlie." you're like, "I have $100 million. Is it horrible right now?" And that's that's kind of a weird place to
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be in where they're like, "Do we envy you or do we feel sorry?" You know, because you had a lot going.
00:09:46
Yeah. No, but but but when somebody poses those questions, um, what do you think would have happened if I had said,
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"Um, I'm I'm not." And how how do you uh plan on helping me? Yeah. What are you doing?
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Like, do you have a guest room? Do you have uh Yeah. you know, do you have a do you have a stocked fridge? Um,
00:10:05
is there crudete anywhere that I could have access, you know, any right? Um, so
00:10:11
it's like Facebook moms putting on Facebook, I don't like when you showed a picture of your kid in the front seat. I
00:10:16
you should never like what do you care? Are you really you really that worried? Anyway, we got so much to talk to
00:10:22
Charlie about. I also want to just insert one thing on winning and also the way you said winning.
00:10:27
Winning, you know, did that influence Trump kind of because he really works a
00:10:33
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 there. Did you
00:10:40
win? Yeah, I win. I'm winning. I'm winning more. You know, I don't know. It's just a interesting interaction
00:10:46
historically, but who knows, right? But the but the book gets into the genesis of of that material.
00:10:52
Oh, that's what I'm I'm so happy to hear. The book of Sheen. Yeah, thank you. Um and it's um you
00:10:59
know, I I I kind of kept it uh kept it a secret for years that that it wasn't my
00:11:04
original material that it was it was inserted into my brain sort of as a pep
00:11:09
talk like a couple days earlier by a baseball player from the Giants named
00:11:14
Brian Wilson, a guy nicknamed the beard. remember the beard? Oh, yeah. So, yeah, I I was watching a highlight
00:11:21
package of his and I told my pal Tony Todd, I said, "Hey, I want to I want to talk to that dude and the next day I was
00:11:26
on the phone and he just rolled out all all that stuff, the stuff that the material that turned into slogans and
00:11:33
t-shirts and folk songs and everything else, right?" And so, yeah, but then I
00:11:38
couldn't really say in the middle of that that that that that whole you, you know, tsunami that I was cresting on a
00:11:45
nuclear surfboard, right? I couldn't I couldn't say, "By the way, all that [ __ ]
00:11:50
was borrowed. That t-shirt you're wearing, not my stuff." I just had to roll with it. And then about midway
00:11:56
through the all the chaos, I spoke to him and I said, "Hey, man. I'm sorry. sorry, I feel like I stole your stuff
00:12:02
and maybe you had uh plans to use it elsewhere. And he said, "No, no, no. It's fine. It's um" I said, "And you're
00:12:08
probably thinking that that that that you got it into the wrong brain and hence the wrong mouth." And he was like,
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"Well, you know, it's I never quite saw it going this far, but if if someone's
00:12:19
going to borrow your material, then then spread the love. Why not?" Well, yeah, cuz it was the timing and
00:12:24
the way you delivered it. We all had you saying it on all over the place. It's you saying it and the rhythm. I
00:12:30
don't know if he was because that was your rhythm, right? Of the way, you know, the winning thing was originally
00:12:36
delivered with that inflection with the high pitch too. Winning winning. Yeah. Yeah. I know. And that's
00:12:44
why it it it got it got, you know, logged in there like that. Um.
00:12:49
Mhm. So, um, his material, but then I think through my filters and, you know,
00:12:56
through whatever else was going on, uh, it it it became what it what it did, you know,
00:13:01
right? Because he was being interviewed sometimes by contrarians or whatever trying to talk to you and you were just
00:13:07
coming back with something so extremely different than anyone would expect that
00:13:13
that was part of the comedy of it. I don't know if he had people interviewing him, you know, in that way, but uh it's
00:13:19
interesting. So, also losing isn't quite as catchy. It doesn't It doesn't losing.
00:13:24
It really isn't. It really isn't. Hey, David,
00:13:30
got an got an announcement to make. Yes, please. Prime big deal days is coming on October
00:13:38
7th and 8th. It's got to be Amazon. Gotta be. Got to be. Got where the deals are. Mhm. You know
00:13:44
the rest. I I actually have a bookmark on my computer of Amazon because
00:13:52
a I did my special for them, of course. Oh, that's right. You were on Amazon Prime. Oh, yeah. This is their annual
00:13:58
sales event from Amazon. Features tons of exclusive deals just for
00:14:04
Prime members. I'm one. Prime members is where it's at because you're getting great deals. You get so
00:14:10
many great things. lot of stuff, you know, deals up to 40% off on these
00:14:16
prime big deal days, October 7th and 8th. So, you have to this is the time to make
00:14:22
your moves because this is it, right? Now, now things I want to get that's
00:14:28
trickier because there's a lot out there that if this is your time to buy Mhm.
00:14:33
what do you get? What What would you be if you had to I put you on the spot. I know it's because you want to think
00:14:38
about it. It's two days of prime big deal packed with great deals, lots of
00:14:44
savings. So, I'm thinking for me, I'm going to
00:14:49
tip a toe in the water with a a subwoofer. I've got a really nice TV. Subwoofer of all things. Okay.
00:14:56
I know. A subwoofer. And it gives you that base thing. I've got a great TV in
00:15:01
this area, but I I need a little oomph. So, I'm thinking a subwoofer. I've got
00:15:06
my eye on that. What about you, David? Well,
00:15:11
uh, I just put on a light jacket in this room. I know you've talked about light jackets. I need I desperately need a light
00:15:18
jacket. Light jackets are where it's at cuz when I travel, I'm always on the plane and
00:15:24
it's just hard to have a big puffer all the time. It's almost like you need one for the plane and sometimes I pack the
00:15:30
puffer. Shocker. I know. I just have this jean jacket
00:15:35
and this is it and it's kind of warm sometimes so I need some light ones when I'm on the, you know, podcast so forth
00:15:41
and so on. Um, you know, I think I need a basketball. I think I need some sort of outdoorsy stuff.
00:15:48
Um, and maybe something for a barbecue cuz I might be starting to get into that, right? And the great thing about Amazon
00:15:55
Prime is to state the obvious, the selection is massive. I want to get a
00:16:02
new microphone that's even makes me bassier and sexier and a new stand.
00:16:08
Yeah, I want to get one. I want you to be bassier than sexier than me. I want a bassy sexy mic and you can put
00:16:13
that in Amazon Prime and boom, you find it, you know. Well, listen. I mean, I'm always looking
00:16:19
for a hot blow dryer. But the thing is,
00:16:24
if you can think it, you can almost find it. Such a wide example.
00:16:29
It is so vast. And I use Amazon Prime constantly to buy stuff. So, this is
00:16:34
just sort of cool these two days where if you're thinking of stuff, a big ticket item and, you know, a great haird
00:16:40
dryer or a travel hairdryer. Nothing wrong with that. That kind of stuff. One, we need you know enough maybe a new
00:16:47
suitcase too, you know, all those kinds of things. All right. Well, now is the best time to get a great deal. Shop deals up to 40%
00:16:53
off. Don't wait. Start making your list now. Plan some stocking stuffers for
00:16:59
Christmas. Shop Prime big deal days October 7th and 8th exclusively for Prime members. Charlie, here's a dumb
00:17:05
question. Go ahead. You got You got one question. Go ahead. He can talk too though. You can talk.
00:17:11
Thank you. Um, have you and I ever met, Dana? I don't think we've ever met.
00:17:16
I don't think so either. No, I mean either. Yeah, we almost Fred Wolf was doing some kind
00:17:22
of movie and you were in it and do it. Yeah. Mad Families. Yes. And I was for a
00:17:28
while I was going to do that, but I just was doing standup or whatever I was doing, but we would have met then. Yes. Yeah. And and David and I had a
00:17:36
scene together. Do you remember this? Oh, that's right. Matt found. Yeah. Do you remember? I I like rewrote it and I turned it in like three pages
00:17:43
and I came to you like five minutes before we were going to shoot it. I'm like, "Let's do it this way, man." I was
00:17:48
[ __ ] hammered, dude. I was hammered that day. Uh and apologies. Um, no.
00:17:53
But we did we did have a nice vibe and a nice rhythm and a nice thing in in that
00:17:59
scene, didn't we? Yes. I remember that was uh Nia Rivera was in that movie. Little was Lil Re in
00:18:06
it. Li Lil. Yeah. Lil Re. And yeah, I I do remember coming
00:18:12
to do one scene and I had to speak with everybody. I don't remember enough about it, but if you we if we did a collab
00:18:20
uh that uh I hope it came out right. Mad family sort of was we call it under the
00:18:25
radar because it was on Crackle. It was on Crackle. Yeah. Crackle
00:18:31
um turned into an app. It was supposed to be like Netflix and then it kind of wasn't. Like very kind of wasn't
00:18:38
wasn't um Yeah. They they they kind of bailed on it. You know, Charlie, do you remember the story of Tom Herz?
00:18:46
try to put a show together with us. And it was after you left Two and a Half Men. And Tom Herz in all his wisdom was
00:18:54
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 was on uh Spin City,
00:19:02
I think. Also Spin Oh, Spin City. And then he came cuz he worked with you and he knew you.
00:19:08
Sure. And then and then um he came to me and said, "What about you and Charlie
00:19:14
doing a show?" And I said, "Isn't Charlie a little bit in the doghouse with the CBS?" Cuz it was literally in
00:19:22
the middle of all that. Oh, yeah. And he says, "Uh, well, uh, Les
00:19:27
Moonveves likes this idea." I was like, "He does." Even in the middle of Char I think
00:19:32
either you guys were suing each other, there was some pure chaos obviously. And I was like, well, uh, and then it kind
00:19:39
of fizzled out, but I thought it would have been fun back then. That was, uh, it would have been kind of a fun pairing.
00:19:45
Yeah. So, it it No, it would have been awesome. And so, it would have been that instead of Anger Management, right?
00:19:52
Oh, yeah. Maybe. Yeah, that's right. I think that's what you went into next. Oh, yeah. Was Anger Management was a 9010 deal.
00:19:58
It was in It was 1090. Yeah. Yeah. Those are those deals, Dana, where you would shoot, it was sort of a new
00:20:04
formula where you'd shoot 10 episodes and if they liked it, they'd buy the back 90.
00:20:09
So, it's very interesting because you gamble and Charlie gambled and won again and he got
00:20:17
a hundred out of it, right? Yeah, we got to 100, but it didn't um it didn't it didn't catch fire like like
00:20:23
like we were kind of hoping, you know. Sure. Um but it's interesting. It's it's literally like a 10 episode pilot. Yeah.
00:20:31
And so then they take the the average number from those episodes that air and
00:20:36
it has to get above a certain threshold and if that happens then it activates the next 90.
00:20:43
Yeah. 100 episodes. You get 100 episodes and you get backend on it or
00:20:49
Exactly. Yeah. You take a lot less upfront salary but you you know have an ownership position um that's pretty
00:20:56
significant uh when they work. But this one because I wasn't um I wasn't ready
00:21:03
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
00:21:09
show. It was about six months after. Yeah. That's that's pretty fast. Yeah. Yeah. Which for me probably felt
00:21:16
like a weekend, you know, at the time in the middle of all that. Yeah. Um
00:21:21
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
00:21:28
sometimes you're doing two shows a week or you didn't finish the second show from last week so you start the week
00:21:34
with that so you're really trying to focus on three shows that week and it's just
00:21:39
and it doesn't uh yeah I think a lot of the process um suffers you know not the thing to get you off drugs
00:21:45
that's for sure definitely not no certainly not most of the casts end up on drugs when
00:21:52
they do the 1090 thing I'm sure because of the the pressure I heard of my friend a friend of mine that
00:21:58
we all know just did a 1090 deal or 9010 whatever we call it and uh I don't think it it kicked in.
00:22:05
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
00:22:12
something you get some money but there's a big uh high reward. Sure. Wait, your your your friend did
00:22:18
one uh recently. Recently? That's what I had heard. Are they still kicking those around?
00:22:24
Wow. Uh because I thought they kind of went away. Was it a multi?
00:22:29
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 uh
00:22:37
cuz I don't want to say anything about his real name because maybe he would feel like, oh, it didn't get picked up, but I'll tell you after. And um
00:22:43
that's very interesting though that the 1090 could still be floating out there when syndication isn't quite as
00:22:49
valuable. Obviously, you were you were sort of one of the last, not the last, but
00:22:54
you your show two and a half men which is still on you know honestly too much and um it's on probably 12 stations at
00:23:02
any given time. When was the end? I mean it was that when this uh the syndication thing
00:23:07
started Big Bang was one of the biggest endings. Sure. Modern Family,
00:23:14
you know. Um when when was it on as far as like when was it like actual broadcast?
00:23:19
Yeah. the block when syndication was a really big thing still, you know, cuz that was Seinfeld the '9s and so forth,
00:23:27
but I guess it got that pop and you were making a really good good salary.
00:23:32
Yeah. You know, um I mean I I was I was trying to negotiate my way out of it. I
00:23:38
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
00:23:44
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
00:23:52
basically. Yeah. I was calling they said yes. Okay. They said yes. And I was like but
00:23:58
because I had a conversation with my manager when I was in rehab when they were trying to negotiate for uh eight
00:24:04
and nine and I I felt like seven had just I kind of just reached my limit. I
00:24:10
didn't see that we had a lot of stories left to tell, you know, and I just I' I'd completely lost a passion. um tons
00:24:17
of tons of [ __ ] in the background in my personal life that wasn't, you know, I'm not I'm not blaming anyone, but it was making the job
00:24:23
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
00:24:29
I if I go back, I have a hunch that that something is going to go it's going to
00:24:35
go horrible. Dam's going to break. Dam's going to break." Yeah, man. Um, now do do you think that was a
00:24:41
self-fulfilling prophecy or do you think I just I just knew that that's how the planets were going to be
00:24:47
misaligned? Well, I think you know when you get overwhelmed. I think you know I mean everyone says money is the key thing but
00:24:53
when you already have money you've been rich probably since Apocalypse Now. You've had money a couple beans in your jeans. Apocalypse Now platoon
00:25:00
Red Dawn. He got back in on Red Dawn. It was it was over. It's still it's still paying. Yeah. Red
00:25:07
red dawn covers those Honda Accord payments just alone. So you got that and then you go everyone's your life is great with money
00:25:14
but it it sounds stupid but it does complicate a lot of things and you've got so many complications going on and I
00:25:20
think you had a trailer on the set as opposed to a dressing room. Did you have a bus or something or my I had I had a tour bus.
00:25:27
A tour bus. That's what I had heard. Yeah. I was jealous when I heard I had a marathon coach. Um it was pretty
00:25:33
cool. Right outside the stage door probably. Right. Like where you walk out and then
00:25:38
so you shoot. It was right there. Yeah. You shoot, you go in and wait and then you come back in and do your scene.
00:25:44
So you can do whatever you want in there obviously and probably took advantage of that.
00:25:50
Um two and a half not so much. Uh the stuff before it and the stuff after it
00:25:55
ve very much so much. Yeah. So um when did you first feel like incredibly
00:26:02
wealthy? What was it after Wall Street or when or for you, you know, you're in your early 20s? When did you kind of go,
00:26:09
"Holy [ __ ] I'm a millionaire or I'm close to a millionaire." You know, Teddy stuff, right?
00:26:15
It was probably like in like mid 90s. Okay. Yeah.
00:26:21
When you're about 30. Yeah. Yeah. But there was a moment early on when I got my first uh acting paycheck
00:26:29
from Grizzly. from Grizzly 2, the Predator. Oh, or the Revenge, as they retitled, the movie Grizzly. They did a sequel.
00:26:36
Yes. Yes. Yeah. And so, um, I made two grand a week and I was there for three. I I
00:26:42
made six grand. I didn't care. I didn't know about taxes or any of that [ __ ] And I went to the bank and just took it all in cash.
00:26:48
And I walked into a clothing store and there were these two kind of fancy uh
00:26:54
vests, not like a western vest, but like a like a camping vest, right? And I could I couldn't decide on the color. It
00:27:00
was like a blue one or a freaking green one. And I was like, I'm gonna take them both.
00:27:06
Whoa. Yeah. And they were like, you know, 40 bucks each, 60 bucks each, whatever. And
00:27:11
just laid out the cash. And literally in that moment, I felt, okay, all right, this is I'm feeling like a big shot.
00:27:18
Sure. And then you all take both. And then you go, you like that [ __ ] And the lady
00:27:24
goes, oh, there's where that came from, [ __ ] Why are you being aggressive? I don't know,
00:27:29
[ __ ] Maybe it's the money winning. How old are you? I'm 13, [ __ ]
00:27:35
I did a Police Academy movie and I was making not much money, but it was more than I ever had in my life. And I saw
00:27:40
some pants in the window in Toronto and I went in and the lady goes, "Those are
00:27:45
$60." It was like Pretty Woman, like those are for rich people. And I
00:27:51
go, "I'll take them." And she's like, "Whoa." Everyone store was like, "Whoa."
00:27:56
And I was like 60s nothing to me cuz I got a $100 in pium. So I bought it. I
00:28:02
literally there's very few times I've felt richer. We all have that story. You know I was
00:28:08
interesting and I'm sure this go in the book that you'd think hey Martin Sheen's dad he's growing up like a billionaire
00:28:15
you know and obviously in the documentary it's it's it's it's
00:28:20
pretty middle class you know. It's not fancy pants. You and you guys didn't
00:28:25
have money. Go ahead. You can see our house in the background of a lot of the Super Eight stuff, you know, and it's not a
00:28:31
mansion. It's not a not a manicured freaking No, no. It's very It's funky and cool.
00:28:37
Great for a kid. But I was wondering if anyone in that posi like I'm fascinated by Sean Penn and
00:28:43
Sean when did you meet Rob Low or are you your friends? Uh did anyone have a silver spoon or you're all
00:28:50
kind of middle class in a sense? We were we were all middle class. Um, uh, Rob's, uh, the the the lows came in
00:28:58
a little later and the reason, you know, he wasn't excluded intentionally, but the footage that the director Andrew
00:29:05
Renzy chose to incorporate was from, you know, the like the like the younger younger years, you know. M
00:29:11
um I think by the time I started making those films with with Rob and his brother Chad, um I think that I think
00:29:17
video uh videotape came into play that it was actually Do you remember this thing called the
00:29:24
uh it was like a Polaroid brand, but it was a Polaroid video camera. Do you
00:29:30
remember this? I never heard it it it developed in the player while you were
00:29:36
waiting and then and then it played it um was it called polar vision I think
00:29:43
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
00:29:52
the Lowe's uh uh dad um was was still in Ohio and their stepdad was a
00:29:59
psychiatrist They lived right down the street. Uh Sean's parents, uh a director, actress. Uh you know, they
00:30:07
they were they married till the day they both died. Um and so but nobody was
00:30:12
nobody was rolling. Nobody was driving a fancy car or or fancy duds or or you
00:30:18
know, picking up a check. Um, so yeah, it was it was it was really a cool time to to just experience all of that and
00:30:26
not have a ton of uh excess and special effects and [ __ ] sort of in the way
00:30:31
of of of of those memories, you know, and Super Eight or whatever that was is so it's just emotional, you know, and
00:30:39
and I I think it's funny like every kid who ever got a hold of a camcorder or whatever, they always want to do war
00:30:44
scenes or crime scenes and want to do a death scene like ah, you know, sure.
00:30:50
Did you have a good go-to move like Oh. Um, yeah.
00:30:56
That the platoon move is a big one. William Defoe.
00:31:01
Oh, yeah. The whole Yeah, the crucifixion. Yeah, that's been reenacted all over.
00:31:07
Yeah. I actually um I have that as a sticker in my phone that I send people when I don't know how to respond. It's
00:31:14
just defo like that. So if you get if you get that, it just means I'm stumped, you know.
00:31:19
[ __ ] send me that. It is interesting of like the trifecta. I think you for Vietnam war films, you
00:31:26
know, you'd say Deer Hunter, Platoon and Apocalypse Now and there was a sheen in
00:31:31
two of them. And I think that that film really along with Wall Street and others
00:31:36
really holds up. You know, Platoon has has some magic to it. Thank you. Would you would you put
00:31:41
Would you put Full Metal Jacket in there anywhere or No, I'd put anything Kubric does is a given.
00:31:46
Yes. Yes, I would. That's a good call. Full Metal Jacket. Anything Kubric pretty much, you know,
00:31:52
sure is just magic. You know, Apocalypse Now, brilliant. Um Master
00:31:59
and Deer Hunter, you know, the mouth, you know, with Christopher Walkin. One of the greatest most intense scenes ever
00:32:05
made. So, yeah. But you're part of that and it's pretty cool. Thank you. Thank you,
00:32:10
Charlie. What movies did you turn down that sting the most? And I'll tell you which one.
00:32:15
If it's Opportunity Knox, I'm so sorry. If it's Tommy Boy, I'm going to be
00:32:21
I'm so sorry. It's between you and me. No, go ahead. I turned down um uh White Men Can't
00:32:27
Jump. Oh, for what? I guess you I would have been Woody. Yeah. And then
00:32:34
um just coincidentally um a bit later on I think it came after maybe before
00:32:40
I turned down um Indecent proposal. Whoa. So I I kept waiting for Woody to send me
00:32:48
some flowers and and thank me for advancing his career like I did. Those
00:32:53
were I found in Decent Proposal. You know, I'm a huge Redford fan. God bless us all. um and to me more and
00:33:00
everything, but I just found the movie very depressing. Woody's character was so like I mean that was the only thing
00:33:06
I'd say about Dodge. I I don't know. It just wasn't my favorite movie. Although it's skillfully brilliantly done. I just
00:33:12
was like, you know, I couldn't get past the thing that all right, they did that. He's got the money
00:33:18
to to to, you know, to lessen the sting a little bit. Yeah. And then spends it all on that chachki.
00:33:24
Right. Right. Like the little jade elephant or something or Yeah. Yeah. Yeah. Or am I misremembering that? Um,
00:33:29
no. It was something weird. It was a very show is love was real and it wasn't about money and it wasn't about this,
00:33:36
but they still have to stay married and live with that moment, right? With the thing with Threadford stuff,
00:33:42
right? Yeah. You know, Charlie's agent wrote back, "Charlie likes it, uh,
00:33:48
but wants to tweak the ending pretty much." And they said, "It's we're pretty locked
00:33:53
in the ending." He said, "That's a pass from Charlie." That's pretty much how we Did you Did
00:33:58
you see Brokeback Mountain and Call Your Agent? Why the [ __ ] wasn't I up for this?
00:34:03
Um I have to admit, um it's kind of one of those films that's always been on
00:34:09
that unseen but need to get to it list, you know, and I think that we all sort of have. Um
00:34:15
so I never I never saw it, but I I hear it's fabulous. Well, it's it's Yeah, it's it's it's a
00:34:21
little heartbreaking, but yeah, the performances are exceptional, you know. Just Yeah. Good Fellas. Good Fellas.
00:34:28
Were you up for that? I was not up for Good Fellas. No. Karate Kid.
00:34:34
Uh, Karate Kid is is one that um that I actually had. Um I don't know if I could
00:34:40
um classify it as turning it down or describe it as turning it down. It's um
00:34:46
I just I I you know, it's in the book. It's in the dock, I think. Um, and that
00:34:52
I I just asked for some time because the advice from my dad was to was to stay to
00:34:58
honor my word with Grizzly and because I'd already, you know, committed to that
00:35:04
grizzly picture. That [ __ ] bear that bear that bear ate me twice, right?
00:35:09
Jaws on land grizzly. Um, so he said, um, if if if they wait
00:35:16
for you, it's meant to be. Um, if they don't, then it's your you know, your
00:35:22
reputation being a man of your word is going to sell you further than one big movie. I I from a from afar I I I do have a lot of
00:35:29
admiration for your dad. I I did meet him and I did something with him one time. It was just a a charity event. We
00:35:35
were all doing Shakespeare with Tom Hanks. But that's good. Yeah. Well, it was kind of like pretend
00:35:42
fun Shakespeare. Was it in the park? They do that in the summer. was in Santa Monica and in theater and it was
00:35:47
a reading, right? Isn't it a reading? Yeah. But then we all go out on stage and sort of get around and are reading,
00:35:53
you know, I'm doing impressions and things and that Shakespeare, you know, I one thing I was going to ask because fil
00:35:59
people who've been in brilliant films around brilliant people. Uh the you know, you've been across your
00:36:06
your partner, man or woman, and went, "Damn, you know, this this person is
00:36:11
exceptional." or someone who kind of took you back a little bit by just how great they were at this thing called acting.
00:36:17
Sure. Who who who might those Who was that? I I I wanted to bring up the elevator scene with your dad and you
00:36:24
that that was one of those moments um where you actually you get distracted
00:36:29
because you're you become an audience member and then wait but you're in the scene and [ __ ] it's my line. Uh you know what
00:36:37
I mean? It's like those moments and I had I had some of them with Michael Douglas on the same movie. Definitely had him definitely had him
00:36:43
with dad. Um even though he's only in it, you know, just a little bit. James Speder in Wall
00:36:49
Street. I was kind of like going, "Oh shit." So they're doing it like that now. You know what I'm saying? It was like this whole
00:36:56
thing. Um and then Yeah, it um Oh [ __ ] Um u Michael J. Fox. Yeah,
00:37:05
just that when we had a couple we had a couple scenes together, um he he had
00:37:10
transitioned out and I had stepped in, but he but he wanted to stay close enough to it to to like to bridge the
00:37:16
the the transition, you know, and and yeah, we we we did some scenes together and and it was it was other
00:37:24
level talent. I was like out. I mean, you look at back you take a look at Back to the Future. I always
00:37:29
sound like I'm doing Trump. But uh that's hard to do, you know, and I know he replaced Eric Stoultz, who probably
00:37:36
was great, but to be light, play it dramatic, and and ride that whole wave of those movies. Yeah, Michael J. Foxes.
00:37:42
I don't know if he's underrated or appropriately appreciated. But that's a great that's a great question.
00:37:48
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
00:37:54
reason. uh you know, not just to to celebrate and to honor him, but also because that's like that's my last
00:38:00
outpost um before going on to two and a half. So, I was kind of symbolically
00:38:06
implying like, okay, I borrowed a little bit from this dude, you know, cuz there was tons flying off of him and took it
00:38:13
over to that thing and we know we saw how that thing went, you know, so
00:38:19
Well, it it's rare. Can you imagine how excited when they they get two and a half men together and Chuck Lori and
00:38:25
there 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
00:38:32
started in spin city but then um you it's hard to find a leading man
00:38:37
handsome leading man who can also be very funny you know so they must have been you know
00:38:43
high-fiving at some point behind the scenes like you know just just because you're you're
00:38:49
you're great at this too, you know. Thank you. Thank you. Um, but it was all it was just playing the straight man,
00:38:55
you know, and when I did it in the hot shot, you know, but yeah, and some of that shots. That's right.
00:39:01
Well, when I did it in Hot Shots, I was I was borrowing, you know, a lot of stuff from Leslie Nielsen, you know.
00:39:07
Oh, who better to borrow. That was the theme of that was sort of the feel. Love that movie Hot Shot.
00:39:13
Oh, thank you. Thank you. And then I was borrowing stuff uh from Ted Dansen on Cheers for for for two and
00:39:21
a half. But I know he's a sober bartender and I was a drunk jingle writer, but just as far as the the
00:39:28
straight man and and you know what I'm saying? He's he's he's kind of the anchor and all the all the craziness
00:39:35
revolves around, you know, orbits his his his star, his planet. But you're not putting huge spin and
00:39:40
overacting. You're not like Kramer, you know what I mean? You're just saying your lines
00:39:45
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
00:39:52
like Andy Griffith was to Right. Right. Right. Yeah. But thank you. That's but
00:39:57
especially coming from you guys. Come on. Two two you know veterans
00:40:03
um and and and you know extremely successful veterans. Um to get comedic
00:40:08
compliments from you guys is really badass. So thank you. Well, don't you and your and your own personal life, you
00:40:14
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 I was this
00:40:20
was maybe a clumsy thing, but, you know, I thought of people who get out fast, you know, and it's it's a rare, but it's
00:40:28
kind of come that are very talented like I'm talking about Woody Allen and I'm talking about the Beatles, Bob Dylan,
00:40:35
you know, by 2122 Brando and you were kind of in in that group in a way. I'm
00:40:41
just saying loosely because you came out so good and so showed so much talent. But you know who musically who's your
00:40:48
who's your north star like when you the cannon of rock and roll? Are you Pink
00:40:53
Floyd? Are you are you Neil Young or Led Led Zeppelin?
00:40:58
Oh I just watched that documentary on the plane becoming pretty good.
00:41:05
Yeah. Yeah. I think they got a shot. That's probably legendary frontman Led Zeppelin. Yeah. What did you think of the doc? Did
00:41:11
you did 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
00:41:17
to know just to where I knew them, you know, and uh but it was very interesting and everyone loved it. So, I watched on
00:41:22
the plane. It was perfect. I ate it up very quickly. I love Yeah, it's excellent.
00:41:27
What was your thoughts? I love playing. I I would have liked that they got to if they'd taken it to Zep 4,
00:41:34
right? It could have gone. Yeah, because that's the one because they only started to get to the stuff I really liked and I was like,
00:41:40
"Wait, is that it? It's over." I was like, "Go, go, go, go, go." Yeah. Oh, we're landing. That's true. It was interesting for a
00:41:46
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
00:41:53
something like really go song to song. I think they showed one full song. I think it was rock and roll. They showed
00:41:59
the whole I think and I was like this is the one is probably I mean as good as any. Uh,
00:42:05
oh, question, Charlie. You collect things and uh I'm sort of been in your orbit. We're we're roughly the same age,
00:42:11
roughly in showbiz. You're you're obviously doing a ton of stuff, way
00:42:16
more, but in a weird way, I remember I'd heard I was at an Elvis auction at
00:42:22
Butterfield. And Butterfield in the old days, I sometimes buy collectibles and [ __ ] I think you're in a maybe baseball
00:42:29
cards. I've always heard that. And sure. Was there an Elvis green MMX you bought ever? Cuz I think I
00:42:36
had my eye on one of those. Wow. I said I think Charlie Sheen got it. You know, I'd love,000.
00:42:42
That's the kind of rumor that you want to embrace. That's a cool one. That's cool cuz then when the bill comes, everybody's kind of waiting for
00:42:48
you to drop that thing, right? Um cuz you can buy
00:42:54
D. I bought an Elvis set list, you know, like he wrote on the on some Michigan Hilton. He was writing all the songs
00:43:00
like Love Me Tender. His handwriting and [ __ ] Oh wow. And so I bought that and I bought a gun
00:43:05
he had and I bought something else. But I wanted this Amx but it was too rich
00:43:11
for my blood. And uh what did it cuz I didn't buy it. I I I never This is the first I'm hearing about this Elvis auction. Um it sounds
00:43:19
awesome. What How much did the MX go for? 50,000. 50,000. And that was 20 years ago.
00:43:26
Wow. because I was at the auction and Joey Espazito was there so they were like authenticating stuff
00:43:33
and I bought a watch and I don't have I don't think anything left from that because I lost the set list and
00:43:38
but I bought stuff before and I thought oh I think Charlie does um maybe baseball cards or just or maybe
00:43:44
baseballs I don't know but yeah I I've got Are you in and out of that biz or not? I've sold everything.
00:43:50
Okay. And and I should have come to that garage sale. Jesus Christ. What what did you how what did you sell that was a little bit
00:43:57
I I had I jeez I I had something like from every era. I had a lot of Babe Ruth
00:44:04
stuff. I had that famous um long white overcoat that he's seen in tons of
00:44:10
photos. Oh, had the coat. Oh, you had the coat. Yeah. Yeah, I had the coat. I mean, there's probably more than one, but I
00:44:15
had one of three probably. Um I had uh a lot of jerseys. um had a lot
00:44:22
of caps, a lot of hats, some great bats. But there there was a turning point moment where um cuz I had these cool
00:44:28
cases built at my house up in Malibu Lake years ago and I had been to the
00:44:33
Hall of Fame for the first time and I thought kind of this is back in like in 1991 and I thought what they had how
00:44:41
they had set it up was a bit shoddy. I thought this I could see like a moth like down in the corner behind the glass
00:44:47
and I was like what are they doing? Right. Right. Yeah. And so I I I I was inspired
00:44:52
by it. I wanted my cases in my house to be like nicer than the Hall of Fame in Coopertown, right?
00:44:58
And so we brought in the right people and you know um and they and they delivered
00:45:03
that, right? M but um then yeah, a couple years later I
00:45:09
was looking for something and I opened a dresser drawer up in my bedroom and there's a 1941 Ted Williams road jersey
00:45:17
like just folded nicely and in the drawer and I had I had that, you know, it's the area hit, you know, 406 and all
00:45:24
that and and I had that moment of if I don't have room on a wall for this, like
00:45:30
this is the last time that anybody ever did the thing he did while wearing that then I need to I need to recirculate a
00:45:38
lot of my these artifacts and antiques and just let others enjoy them and and then I I uh Leland's put together an
00:45:45
auction and it uh it was all sent back out into the world, you know. Interesting. and and some cards. They're
00:45:51
not a Honus Swagner card or was that I I had one called like the five pinhole
00:45:57
card because they're they they're so graded so anally and they have to describe
00:46:02
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
00:46:10
bedroom and Oh, and yeah, but don't you think you'd at least just keep using the same hole?
00:46:16
Why did he have to make five holes? Um, no, those [ __ ] They're ruining
00:46:22
cards for the future. I don't know. They Yeah, they really were. So, um, but I'm sure that went a little pricey.
00:46:27
Uh, yeah, it was it was up there, but not nearly when the when that Wagner
00:46:33
card really got everyone's attention when Gretzky partnered with um was it
00:46:38
McNall, guy named and they paid like what' they pay for that like 500 grand. Everybody was like,
00:46:43
"This is out of control." And and now now you think about that, that's like chump change, right?
00:46:49
Yeah. I mean, all that stuff just keep it's one of the few niche places that
00:46:55
just keeps going up faster than stocks. It's they just when you people have a passion and they
00:47:01
collect their passion and even, you know, Jay Lenel probably has made more money or, you know, he
00:47:06
won't sell his cars. No. But he probably if he did he'd make more money off his passion than even
00:47:12
comedic career. You know, it's very I I have a friend who collects antique bottles and it's his collection is worth $3 million. He's
00:47:19
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
00:47:24
and you dig where they're excavating a building where you're digging down a hole and then you see this little two
00:47:30
inches of ash and that's 1906 the earthquake and the fire. Then you go further and you're pulling out shoes and
00:47:35
stuff. Once in a while you get a bottle, you know, that's worth $50,000, you know. So, it's interesting to
00:47:42
further and you're in China. Yeah. You know, one thing I was going to ask Charlie about because I was seeing, you know, Cooperttown has this, I want
00:47:48
to have more. And we all have this 10-year-old boy inside of us and it's sometimes it's it's necessary to have
00:47:54
success is just to have a fair play uh competitive instinct. They do that. I
00:48:00
mean, Nicholas Cage was so competitive. I did a movie with him and we just made made fun of the competition, you know,
00:48:07
because because um Kurt Russell was in Tombstone and he had a line in the movie, "You're gonna throw down, boy."
00:48:15
If you remember the movie to Billy Billy Bob Thornton who weighed 220 pounds. So when Nicholas thought I did something
00:48:21
good, you threw down. You really threw down today, you know. Wow.
00:48:26
Wow. What What film did you guys do? Uh the films I do are aren't even on video and they they're banned from Earth. No,
00:48:33
it was uh Trapped in Paradise. Oh, we wandered around in the snow. We fell
00:48:38
around in the snow, me, him, and John Love it for for three months and somehow they put something together. Okay. But
00:48:45
Nicholas was a blast and one of the funniest and brightest guys I've ever met.
00:48:51
Was he one of your Malibu guys? Not Nicholas Cage, your your relationship with him. Yeah. No, he's not a Malibu guy. Um, he was a
00:48:58
town guy and a um and a and a Bay Area guy sort of back and forth, you know.
00:49:04
I'm sorry, what was the last question? Um, well, I I just wanted to know about your relationship with him, you know, because
00:49:09
you guys kind of hung out. I know there was, you know, extracurricular activities, but just as a person,
00:49:15
I I found him very charming and he's he's one of my favorite people. Um,
00:49:21
I I I we we don't see each other enough. Um but when we do it's uh it's it's it's
00:49:26
it's quite special. It um yeah because you because you talk about his
00:49:31
intellect, you know. Um and then you wrap that inside of this this you know
00:49:38
outlandish sense of humor just that is rooted somewhere outside of what what us
00:49:44
mortals can grasp. And it's uh it's a it's a it's an insane and beautiful mashup.
00:49:49
He he never saw acting as having to be accurate, you know. he just found that you could do whatever you wanted with
00:49:55
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
00:50:02
this girlfriend or something like that and he goes, "I'm going to do Daniel D Lewis from in the name of my father in
00:50:09
this take." So, he comes all of a sudden he comes out screaming, falls to his knees, why why?
00:50:18
And I was like, you can do that? I mean, he's a he's a he's a unicorn. I mean, there's no rules with him. There's no
00:50:24
rules with him. And and to have that kind of courage in inside that that that those spaces is
00:50:32
it it's it's to be marveled at, you know. Yeah. Oh, I got something. When was Tom Cruz
00:50:37
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
00:50:45
when Chris uh Sean's younger brother Chris Penn dropped out of high school and and bumrushed that set of taps
00:50:52
on the other side of the country, um he came back talking about this guy named Tom Cruz.
00:50:58
Oh, in my mind I added a Z and I thought he was Latin. I thought he was a Mexican or Spaniard or something, right?
00:51:05
And then when I met him, I was like, "Oh, you're from Oklahoma." and and then he smiles and and and then you start to
00:51:11
engage his personality and his intellect and you're like, "Yeah, this guy this is there's something going on here for
00:51:17
sure." But Ailio and he became really tight because they um they were
00:51:22
auditioning for The Outsiders at the same time and helping each other prepare
00:51:28
for their auditions, you know, and then they both got it the the different roles. Um and they've they've they've
00:51:34
been great friends ever since. So, I was, you know, I was younger than them, so I've kind of like tagging along. But,
00:51:41
um, anytime I've, you know, seen Tom over the years wherever, he's awesome,
00:51:46
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
00:51:53
basically a baby, you know. I may be hung from a wire once, but, you know, he's hanging on to airplanes and I know
00:51:58
like I'm strapped down. He's holding his breath for six minutes. I mean, you can't even What the [ __ ] So, you have
00:52:04
to see the movie. What the [ __ ] Yeah. Right. Yeah. But do do you think at some point
00:52:10
um he's gonna want to get back to like a magnolia?
00:52:15
Right. Right. Oh, yeah. Right. Which was a work of art and he was spectacular in that.
00:52:22
Yeah. What you got to respect the [ __ ] I'm sorry. Was that it? Was that was it? That's it. Yeah. Respect
00:52:28
the [ __ ] Yeah. He said it better than I did, but yeah. Um he's a force of nature. It's funny
00:52:34
because Sandler has the ability to go from a Paul Thomas Anderson movie to a
00:52:40
big broad happy go and he goes back Noah Bomb backach then he goes back to abroad
00:52:45
and I think Tom obviously can do anything he wants but you're right these are important but Mission Impossible to
00:52:51
Top Gun it's huge huge blockbusters but would he want to go smaller would he
00:52:56
want to go he could get an Oscar he's great I think if Christopher Nolan called him
00:53:01
or somebody like that he might get his attention I think so. I think so. I mean, he does
00:53:06
want to make movies that fill theaters and give people that that that that experience that they that connects them
00:53:11
back to their childhood. That that he's the savior of that. He's I think he's made himself the guy, the
00:53:17
spokesman. He and the filmmakers know this, but it was in Roman Holiday long time ago, but
00:53:23
basically nonverbal with music. So, the end of Top Gun, you have a six-minute montage
00:53:29
of the end of the movie of people tearing up, no real dialogue and saluting and we we we're alive and we
00:53:35
did this and I've seen other films do that F1 and uh where there's this silent movie added
00:53:41
onto the movie and it's very affecting, you know, that three or four minutes where you're seeing them in tears
00:53:47
looking at each other and it's uh all a lot of the blockbusters are using that now. So, it's just kind of interesting
00:53:53
to me. The Top Gun really got me emotionally because, you know, I hear Han Zimmerman, I hear
00:53:59
just the music. I'm kind of It gets me emotional. Sure. And then you see Tom Cruz is really good
00:54:04
at hugging someone, coming back. He's got this look in the tearary eyes and get you.
00:54:09
Yeah. Yeah. He he he insists that that that that we experience that moment with
00:54:15
him. Right. Right. Yeah. Now, is that the first Top Gun that you're referring to or is that is this the second one?
00:54:22
Second one. Got it. Got it. Okay. Yeah. Which came out of nowhere and was a in movie theater big hit when the industry
00:54:28
really needed it obviously. But um and they tried to they tried to stream it, didn't they?
00:54:33
Whoa. He not on his watch. Was like no no
00:54:39
stuck to his young gun. Speaking of that, in 1988,
00:54:44
thank god they didn't wait 30 years between Grizzlies, right? I mean, that would have been a
00:54:52
been a disaster, you know. [ __ ] I think we're out of time, Dana. I
00:54:58
think we had a I think we had a wrap with Charlie Sheen. Any wrapup questions for this guy?
00:55:04
Not Not really. I think the book is The Book of Sheen, the documentary. I mean, we you know, we consciously we talked
00:55:10
about it. We didn't want to We We know you've done a lot of press, so we wanted to make this lighter and more fun and
00:55:15
wanted to pick your brain about relationships with your dad or whoever. So, Sure. No, this is this has been
00:55:21
incredibly refreshing. Um, good. That's what we wanted. Thank you. And and if I I'd like to
00:55:27
believe that I get invited back and that that'd be amazing. And then we
00:55:32
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 totally just want to
00:55:39
get didn't want to give you anything but yeah. No, and and thank you. I appreciate that. But I do have a
00:55:45
question for David. Um good. And um there was a weird moment during
00:55:52
the fight, right? And as soon as like I'm, you know, and and Michael's he's a lovely man.
00:55:59
He's just beautifully all over the place, but what a good dude. But when when I look over and I see Dave's name
00:56:08
on the chair next to me, I was like, "Okay, all right. I I I'm I'm I'm gonna
00:56:13
have some backup. Reinforcements come in." I don't know why I thought that, right? Yeah. Yeah. So, he sits down and I'm like, "Did they
00:56:19
plan this knowing that we're this was already scheduled?" Right. So, they finally cut the chairs apart.
00:56:26
Everybody's having a great time. And I look up and I see this this giant rig
00:56:32
like where they had speakers and the lights thing. It weighs like, you know, four 100,000 tons, right?
00:56:39
And I said to Dave, I said, "If that if that breaks loose, we're we're clearly in in the crush zone, right?" And I
00:56:47
said, "Are you cool if I'm the last guy like on this planet that you interact
00:56:54
with?" And he took a beat. took a beat and and said something to
00:57:01
the effect of, "Yeah, yeah, I I I think I'm okay with that." And I said, "Good,
00:57:08
cuz I'm okay with it being you, too." You know, and so we really bonded there. I felt like we bonded there, man. And
00:57:15
clearly it didn't fall. But is that No, but I like that you put that in my head. Uh I think I was taking a beat
00:57:21
because I was thinking, what are the Does he know something I don't? Is this going to fall? And then Marshon Lynch
00:57:27
sat in front of me and blocked 110% of the fight. Oh my gosh, that's his head is this big. I go, "Wow, wait,
00:57:33
is the fight over?" I I go to watch on the screen now. Oh, I do that. Oh, I do that all the
00:57:40
time. Can this fall or is this Also, Dana, they show they show Michael J. Fox on the screen and I go, "For no
00:57:46
reason." You can tell he's still mad at you, Charlie. That was funny. That was funny. Yeah.
00:57:52
Based on nothing. That was excellent. That was fun to be at the fight with laughing because I
00:57:57
want you. Would you do you mind doing Michael J. Fox Casualties of War just for Charlie?
00:58:02
Oh, me? Uh, remember that movie Charlie? I do. I You love Michael J. Fox
00:58:09
is grabbing this. Yeah. And he's like, "Hey, Sarge. Hey,
00:58:16
you got to give me a minute on this here, Sarge." Oh, Christ. She's just a farm girl, Sarge. What are we doing
00:58:23
here? Exactly. That's amazing. It gets me gets me every time. Such an
00:58:30
obscure specific impression. Why J Fox in that movie? I was like, and Clarky was John C. Riley and Sean Ben's
00:58:37
like, "Fucking Clark, throw her down and take her clothes off." I'm like, "Hey, we got to get these VC gs. These VC go whore." I'm like, "What is
00:58:45
this?" I thought it was a fun comedy cuz it was Michael. I'm like, "This movie took a dark turn
00:58:51
and never turned back." Yeah, they're whatever. That's a funny
00:58:56
Sean was hard on him during that film, wasn't he? Oh, on Michael Foxid acting. I had heard
00:59:03
about that. Yeah. Yeah. Yeah. Apparently, he was just, you know, none of the didn't didn't want to cuz he's like, you're a sitcom guy kind
00:59:10
of. Well, that maybe that, but also just the character. Just the stay in character. Yeah. Resentment, you know?
00:59:16
Yeah. The alpha alpha. Yeah. Do you know I've only I've only worked with Shawn on Two
00:59:22
and a Half Men? I've only worked with Shawn in a in a in a comedic setting. He was brilliant.
00:59:28
It's It was our first episode, second season, and he's in a men's group and it was Elvis Castello and Harry Stanton and
00:59:35
me and Bobby Cooper. It was awesome. Um, but isn't that a trip that the first time he and I actually
00:59:41
I thought you done I thought he was one of your old movies. No, just the stuff you see in the dock where he shoots me
00:59:48
in my own backyard and then stuffs me in the refrigerator for Ailio to discover later on. It was nuts, you know.
00:59:55
Yeah. He can be very funny though. I think he went on Friends was very funny. Such an interesting character.
01:00:02
I go, "Wow, this guy's talented." Oh, right on. Right on. You know, Charlie, we'll do it again and we'll do it. We
01:00:07
got more to talk to you about because we'll do it in person.
01:00:14
Hey guys, if you're loving this podcast, which you are, be sure to click follow on your favorite podcast app. Give us a
01:00:21
review, fivestar rating, or maybe even share an episode that you've loved with a friend. If you're watching this
01:00:27
episode on YouTube, please subscribe. We're on video now. Fly on the Wall is presented by Odyssey, an executive
01:00:33
produced by Dana Carvey and David Spade, Heather Santoro, and Greg Holtzman, Mattie Sprung Kaiser, and Leah Reese
01:00:40
Dennis of Odyssey. Our senior producer is Greg Holtzman, and the show is produced and edited by Phil Sweet Tech.
01:00:47
Booking by Cultivated Entertainment. Special thanks to Patrick Fogerty, Evan Cox, Mora Curran, Melissa Wester,
01:00:57
Hillary Shuff, Eric Donnelly, Colin Gainner, Shan Cherry, Kurt Courtourtney,
01:01:03
and Lauren Vieiraa. Reach out with us any questions be asked and answered on the show. You can email us at fly
01:01:09
onthealla.com. That's audacy.com.

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This episode stands out for the following:

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Episode Highlights

  • Charlie Sheen's Rise to Fame
    From a cameo in Ferris Bueller to a sitcom star, Sheen's career is unparalleled.
    “Charlie Sheen, the one and only. Internationally known as God is my witness.”
    @ 00m 32s
    October 02, 2025
  • A Comedian Unleashed
    Sheen's rants during his chaotic period are seen as comedic rather than mad.
    “They're the work of a comedian. They're just really funny.”
    @ 07m 30s
    October 02, 2025
  • The Origins of 'Winning'
    Sheen reveals the phrase 'winning' was inspired by a baseball player, Brian Wilson.
    “I couldn't say, 'By the way, all that [ __ ] was borrowed.'”
    @ 11m 04s
    October 02, 2025
  • The Value of Passion
    Collecting artifacts can be more profitable than stocks, as passions drive value.
    “It's one of the few niche places that just keeps going up faster than stocks.”
    @ 46m 49s
    October 02, 2025
  • Nicolas Cage's Unique Style
    Cage's fearless approach to acting defies traditional rules, showcasing his creativity.
    “He never saw acting as having to be accurate.”
    @ 49m 49s
    October 02, 2025
  • Tom Cruise's Impact
    Cruise's ability to connect with audiences makes him a significant figure in cinema.
    “He’s made himself the guy, the spokesman.”
    @ 53m 17s
    October 02, 2025

Episode Quotes

Key Moments

  • Charlie Sheen's Career00:32
  • Comedic Rants07:30
  • Winning Origins11:04
  • Rediscovering History45:09
  • Unique Acting Styles50:18
  • Emotional Connections53:53

Words per Minute Over Time

Vibes Breakdown

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