**Editors Note:* This article was originally published in the June 2001 issue of Playboy magazine.*

In May 1998 Charlie Sheen—whose party-filled lifestyle seemed to eclipse his work in films such as Platoon, Wall Street, Major League and Hot Shots—was home, alone and bored with snorting and smoking cocaine. No problem: He’d discovered an unused rig a junkie friend had left behind, and had an idea. Sheen had never shot cocaine, so he loaded up the syringe, emptied the contents into his arm and waited. To his surprise, he felt nothing. So he did it again. All at once it hit him.

Sheen is still around to tell the harrowing story because this wasn’t just another self-destructive day. For once, he couldn’t shake off the night of excess and restart the cycle. He ended up in the hospital, then in the tabloids and finally in court-ordered rehab. That happened in part because his father, actor Martin Sheen, publicly asked Malibu municipal court judge Lawrence Mira (who also handled Robert Downey Jr.’s case) to arrest his son and get him help before he went off the deep end. Martin’s ace: Charlie was already on probation after pleading no contest in 1997 to allegedly assaulting his ex-girlfriend, and since doing drugs was certainly not part of the deal, the judge agreed.

Sheen had finally flamed out after years of living the wild life, and all he had left was a largely unremarkable career and a reputation as the last man standing when the party was over. His appetites for drink, drugs and sex—free or paid for—were extreme. In the beginning (post-Platoon, 1986), the go-anywhere, try-anything lifestyle seemed like the natural endowment of a hot, young, good-looking leading man in Hollywood. Even when the hangovers got worse and the binges lasted for days, Sheen’s stamina kept him upright. He could get back into a work mode, and his abuses weren’t as serious as some of his peers’. In 1995, his career took a body blow when he testified at the trial of Hollywood madam Heidi Fleiss and admitted to dropping more than $50,000 for her employees’ services. Then he survived the near overdose.

Now, more than three years later, Sheen says he is clean, sober, healthy and looking ahead. Not only did he fulfill his part of Judge Mira’s bargain, he even got off probation early.

That doesn’t mean Sheen has lost his relish for living on the edge. It’s just that the edge has changed. Instead of engaging in actual debauchery, Sheen made Rated X, a Showtime movie about adult-film entrepreneurs Jim and Artie Mitchell (Behind the Green Door). Sheen played Artie; brother Emilio Estevez directed and played Jim.

Then, after Michael J. Fox retired from Spin City last year, Sheen joined the cast as Charlie Crawford, the new deputy mayor with a checkered past. Sheen’s reviews have been good and the show has improved in the ratings, even though it airs Wednesday nights opposite Martin Sheen as the president on The West Wing and the Fox reality show of the moment.

Sheen was born Carlos Irwin Estevez on September 3,1965, the third child of Martin and Janet Sheen. He has two older brothers, Emilio and Ramon, and a younger sister, Renee. Because his dad insisted on taking the family on location, Sheen grew up in places that his classmates could only point to on the map. The most memorable trip was almost eight months in the Philippines during the making of Apocalypse Now.

Stateside, Sheen attended Santa Monica High with neighbors Sean and Chris Penn and Rob and Chad Lowe. The group, fast friends, also made numerous Super-8 home movies, taking turns as writers, directors, cameramen, etc. Sheen says he was a normal kid, but he had some problems, including arrests for marijuana possession and credit card forgery. He also used his dad’s charge card to pay a Las Vegas hooker for helping him lose his virginity when he was 15.

Though Sheen appeared as an extra in Apocalypse Now and hung out with older brother Emilio and his Brat Pack friends—wishing he could live their high lives—he became an actor because he admired his dad and “to get my parents off my back” about finishing high school. He found a job immediately in 1984’s Grizzly II: The Predator. He was also offered the lead role in the first Karate Kid but had to pass because of a scheduling conflict. Instead, he waited two years for box-office magic with Platoon, and his face ended up on the cover of Time magazine.

Contributing Editor David Rensin met with Sheen on the set of Spin City and at the actor’s LA condo. Rensin reports:

“In the past, a chance to interview Charlie Sheen was irresistible to the media. He has always been an outrageous and dependable quote. Charlie never minded dissing other actors or recounting a bacchanalian adventure. But he also believed in telling it like it is, or at least as he saw it. Since Sheen was often hopped-up during an interview, the results were invariably compelling.

"Today, Charlie is more wary when it comes to shooting off his mouth. That’s why, before I turned on the tape recorder, he wanted to get to know me. After an afternoon of Spin City read-throughs, we met for a light meal at a local Italian restaurant. He looked at me with eyes scrunched up intently, trying to see if I was someone he’d feel comfortable telling everything to.

"Before dinner was done, Charlie suggested I go to his house for the interview. We spent a long night at his West Los Angeles condo, where we shared a heavily sugared General Foods International Coffee moment, and then met in his studio lot dressing room to go over the intimate details of his rise and fall and rise.

"The first thing that Charlie did when I turned on the tape recorder was complain about another magazine interview in which he was quoted as saying he’d slept with 5000 women. ‘Not true,’ he insisted, with a smile.”

PLAYBOY: Did you really sleep with 5000 women?

SHEEN: [Smiles] Funny. Good start. OK, I want to set the record straight. That interviewer baited me, and I should have seen it coming. He said, “So, Wilt Chamberlain claims he slept with 20,000 women. Is that something close to what you would assume for yourself?” I said, “No, I’m not old enough. That’s impossible. Plus, I once broke it down for Wilt, and during the time span he claimed, there would have to have been a girl every 36 minutes.” The interviewer said, “Well, how many? Ten?” I said, “No.” He said, “Five?” I said, “I don’t know. I honestly have no idea. It’s speculative and borders on preposterous. Plus, I didn’t count.” He pushed, “Well, five?” Finally, I said, “Fine. Fine. Five.” And he ran with it.

PLAYBOY: We did the math, too. That amounts to one a day for almost 14 years.

SHEEN: It’s pretty far off for me [laughs]. Plus, I was in some long relationships that would have made it impossible.

PLAYBOY: Nonetheless, like many things in your career, the story seems bound for showbiz folklore—as attested to by this quote we read at Inside.com: “The only buzz the new Spin City is getting is for the rock-star tour bus Charlie Sheen has parked on the studio lot. And, given the recent publicity about Sheen’s love life"—meaning the 5000 women—"we don’t even want to think about what might be going on inside the bus.”

SHEEN: Two things: One, I got rid of the bus.


SHEEN: At first I tried to make it available as a Spin City clubhouse, but it didn’t work where it was parked. Then I asked myself, If Barry Bostwick or Heather Locklear had one, would I be hanging out in it? And I realized, No, that’s their private space. At the same time, I got tired of feeling like a separatist or an elitist. I wanted to be in a dressing room next to the other actors, in the mix right there on the stage. It was too much of a spectacle, so I just walked in one day and said, “This thing’s got to go.” I still own it. It’ll be out on the road, being rented by other people, to pay for itself.

PLAYBOY: That’s one, what’s two?

SHEEN: I heard recently in Jay Leno’s monolog that I call myself the Machine. I’ve never called myself the Machine. It was a nickname my friends gave me in the old days because when they were all ready to go home or to the ER, I was always the last guy standing, insisting that the party continue. Jay said that with the number of hookers I must have slept with, I should call myself the Automated Teller Machine. [Smiles] That’s kind of funny, and it’s nice to be talked about, but still.

PLAYBOY: Do you want the media to drop your past and get on with it?

SHEEN: I guess there’s a part of me that still embraces or revels in generating some kind of media buzz or controversy. Why? Because it’s immediate attention and it fuels that part of the fire. I don’t want my life to be beige and boring and unquotable.

On the other hand, there have to be more important things going on in the world than my past. But I know that no matter what I do from this point forward—if the show’s a hit, if I make movies that are hits, if I do great social work— it’s always going to be “the former erst-while embattled news fodder.” So I understand why, when I slip a little with something quotable, it’s latched on to. It’s because they can no longer write about my bad behavior. I’m not creating any wreckage or generating any headlines.

PLAYBOY: That wasn’t always the case. How bummed out were you to be the guy publicly fingered in the Heidi Fleiss trial, while so many other Hollywood notables remained nameless?

SHEEN: They went for the easiest target. But it’s OK. I was one of the few guys who were single and young. If I took the bullet, it would soften the attack on the whole community.

PLAYBOY: Are you still paying for sex?

SHEEN: [Shakes his head] I shut that down. I did it a couple times after I got sober and it didn’t feel like it was in keeping with the kind of progress I’m making. It felt like the old me. It felt cheap and stupid. They had more fun than I did.

PLAYBOY: Maybe they should have paid you.

SHEEN: I didn’t want to mention that [smiles].

PLAYBOY: You once said that paying for sex was really paying for them to leave when you’re done.

SHEEN: That’s an old Cary Grant quote. I borrowed it.

PLAYBOY: But you believed it.

SHEEN: To a degree, but also it was about avoiding all that hassle I would encounter going out, hanging out, picking up, taking home, transporting, blah blah blah. All the lies, the deceit. Promising to call and not calling. That’s old behavior.

PLAYBOY: What’s the new behavior?

SHEEN: Believe it or not, I’ve always been pretty old-fashioned. I’m kind of a missionary guy, from way back. I don’t need a leather diaper collection and a lot of fantasies to get sexual. I think the more props you need, the less you’ve got going on with your own sexuality.

PLAYBOY: What changed your attitude?

SHEEN: In sobriety they teach you to think the drink through. Don’t just think about having the drink and how good it’s going to feel. Think through to the next morning, how it’s going to influence you, the shame, how it’s going to trigger the domino effect. If I do that I end up with, OK, I’m not going to drink. It’s the same thing with one-night stands. I appreciate my time in the mornings so much that I’d rather go to bed at night alone than deal with waking up, creeping around the bedroom, being quiet, worrying. Also, I’d like to be with somebody I care about. Something moderately substantial.

PLAYBOY: Can you care about somebody?

SHEEN: Absolutely. Now that I’ve finally gotten to know myself a little bit, I know who I’m bringing to the relationship. Until now I’ve never had the tools to apply in a meaningful relationship. But I’m not looking for it. Right now I’m kind of in love with my job. [Pauses] I just don’t want to live like I used to. And at some point, probably after this interview, I’m going to put a gag order on myself in terms of talking about the past. Seriously. I’ve got to slam the door and deal with the present and the future.

PLAYBOY: As long as you do it after this interview.

SHEEN: I get it. If I were assigned to somebody who had been through what I’ve been through and it was my job to deliver a story, I’d probably want to know the interesting shit and not just how the read-through was on Spin City. But that said, I’m talking about it now because I think I have a duty as a recovering guy to help, to make my knowledge of what I went through accessible.

PLAYBOY: Great. This isn’t the first time that you’ve said you’re recovered. Why should we believe you now, and why did you slip up before?

SHEEN: If I wanted to party now, I’d probably have to do it in the Himalayas, or on Mir. Can you imagine me going down to the corner bar and saying, “Hey, give me a shot of vodka. Put it in a coffee cup.” First of all, I don’t want to party now, and that’s the difference. But if I said, all right, I’m going to do it, where would I go? Publicly talking about this stuff eliminates a lot of options. This is the only disease that wants to keep you looking good while you’re killing yourself. All I can do today is lead by example and remember that I’m powerless over how people perceive me.

Back in those days, I hadn’t gone far enough into it. I hadn’t gotten on the pipe, shot dope, had legal hassles. I was still, in my mind, above the law, a functional, socially acceptable maniac. I’ve always needed lots of proof, and after the past few years I’m convinced of the insanity of my disease and of the insanity of second-guessing myself as an addict.

PLAYBOY: You didn’t believe you were an addict?

SHEEN: I just didn’t believe I was like everybody else. I thought I was unique. I didn’t wake up in my neighbor’s bed. I never crashed my car into some innocent person. I never fired my gun into a crowded shopping mall. I didn’t get pulled over on the fucking highway with a gun and heroin. I didn’t kick a cop and hop a fence. I didn’t fucking take a gun on an airplane. I didn’t kill anybody. I didn’t molest any children. Heidi didn’t send little boys to my ranch. Sure, I did a lot of things in excess. But if you look at the core, the foundation of what I pursued, who the fuck wouldn’t? What red-blooded young American male in my position wouldn’t? All the guys who criticize it would have done the same thing but probably would have died because they don’t have the constitution I was cursed with. The most damage I did was to myself and to the people who got caught in the maelstrom. The worst thing that happened was the overdose. But, then, I didn’t go in with three other dudes who overdosed with me. No, you overdose alone.

PLAYBOY: What about the gun incident in which your then girlfriend, Kelly Preston, got shot?

SHEEN: That was a complete accident. I wasn’t even in the room. She picked up a pair of my pants, to get them off the bathroom scale so she could weigh herself one morning. A little revolver fell out of my back pocket, hit the bathroom floor and went off. It shot a hole through the toilet and she got hit in the leg with shrapnel. I was downstairs, making coffee and she came to the top of the stairs, blood all over her, telling me to call 911. But she was fine. She got two stitches and I had to get a new toilet.

But let me get back to why things are different for me this time. There was just so much more despair and hopelessness for me at the end than there had been the other times I supposedly got clean and came out in public saying, “I’m fine,” but wasn’t. This last go-around was overwhelming.

PLAYBOY: Because of your near-death experience?

SHEEN: That, and just feeling my spirit dying.

PLAYBOY: On the ER table?

SHEEN: No, just day to day, not really wanting to be an active member of the human race.

PLAYBOY: Were you suicidal?

SHEEN: No. But when friends asked me what was going on, I’d use a line from Star Wars. They’d ask, “Can we help?” and I’d say, “Not unless you can alter time, speed up the harvest or teleport me off this rock.”

I remember thinking and feeling and believing that I was not able to stop, that I genuinely was incapable of putting an end to this. It wasn’t even that I didn’t know what to do with myself if I could stop. I didn’t take the thought that far. It was, “My God, I can’t stop. Now what?” Not, “OK, if I stop—” That was a terribly sad reality.

PLAYBOY: So what did you do?

SHEEN: I thought, All right, if I can’t stop, I’m going to take this thing as far as I can. I wasn’t going to dabble and mope about. Let’s get on a horse and drive this fucking circus completely out of town.

PLAYBOY: Meaning?

SHEEN: I decided to turn up the volume. Let’s stop sleeping, let’s stop eating and just fucking party. I was smoking about a pound and a half of cocaine a month toward the end. That’s a lot. It was hard-core—cleaner than crack because you cook it yourself—but so what?

PLAYBOY: That sounds suicidal to us.

SHEEN: Maybe subconsciously.

PLAYBOY: And it all ended up with you in the Los Robles Hospital. What happened?

SHEEN: I got bored with smoking and snorting. A buddy of mine who’s kind of a speed junkie had left a rig behind. It was still in the package and unused, and I thought I would shoot some cocaine. I had never done it before and I was all alone—a good time to shoot, right? [Shakes head and laughs]

PLAYBOY: You loaded up the needle and put it in your arm.

SHEEN: Oh yeah. Fired it straight home. Just like I’d seen in Pulp Fiction, or in that movie with Gary Busey and Dustin Hoffman, Straight Time. And nothing happened. I thought, This sucks—so I did some more. Then it all hit me at once. My legs went out. They disappeared. I couldn’t walk. I tried to get downstairs to get some vodka, to try to bring everything down, and I couldn’t. I was fucking terrified. I thought, OK, I’m going. I checked my blood pressure and my heart rate. My vitals were up, but they weren’t code. Finally, I managed to take little baby steps down the stairwell. It took 20 minutes; it felt like 20 days. Horrifying.

PLAYBOY: Your heart going boom-boom-boom?

SHEEN: From the panic. I thought something really wrong had happened. I didn’t want to just tough it out. I called my bodyguard and said, “Dude, we’ve got to 911 it.” So we did. In the ambulance they gave me a big shot of something to bring me down, and I fell asleep. That’s when the paramedic called the press and sold me like a loaf of bread. This was news, and he wanted to be the one to report it.

PLAYBOY: The paramedic called the media right from the ambulance?

SHEEN: Must have, because there were too many people waiting when I got there. At the hospital I just wanted a shot of Ativan or something mellowing. Instead, I got a doctor who came right into the room and got way too close to my face and said, “You need AA and you need it now.” I’m thinking, Fuck you and your AA. Give me some Valium. Then I drifted into half-sleep, a dream state. I never had an official overdose, but I think that’s where I was headed. Then Dad went on the news, and the judge heard that I had OD’d. I was on this watch for probation. It didn’t involve testing, but I was supposed to obey all laws, so they hauled me in.

PLAYBOY: Didn’t your dad ask the judge to arrest you?

SHEEN: Right. He went on the news and said, “My son has had a drug overdose.” That triggered Judge Mira.

PLAYBOY: He seems to get all the young actors.

SHEEN: Yeah, we keep him busy. But I’ve got to tell you, I really came to respect the guy I initially deeply resented and held so much animosity toward. He could see a little more progress in me each time I’d go in for updates and visits. He’d say, “I have to keep the probation on, but you’re doing great, you look great and I hear great things. Keep up the good work.” I think he was inspired because I was really the first guy who followed his code and held true to what he imposed. I accepted it and knew that it was because he wanted to save my life, not because he wanted to punish me. He saw past the textbook punitive avenues. He dug deeper into himself for something more humane, because he didn’t see a criminal, he just saw a guy who had become a drug addict and needed therapy.

But believe me, I knew if I got loaded I was going away for a while. In fact, people would say, “Oh, you’re just sober because you’re on probation.” I’d say, “Well, maybe today. But maybe tomorrow that won’t be the case.” What you come to discover is, it isn’t how you get there, it’s that you get there. If that’s what it took to get me where I’m at today, so be it.

PLAYBOY: Any temptations afterward?

SHEEN: Sure. I had plans early on, the day I got off probation, to go to Amsterdam and go on a whole run. I wanted to control the disease again, so I could take back the power. Going would have been giving away the power.

PLAYBOY: Why haven’t you ever discussed this part of the experience publicly?

SHEEN: It’s nice to talk about it and know that I don’t have to go through it ever again. That’s terrifying shit. I would have given anything—any movie, any car, any woman, anything—to just be normal. I’m talking about it because some kid who’s struggling with his own addictions might read an interview I’ve given, looking for something inspirational or truthful that might save or deter him.

PLAYBOY: We don’t mean to be naysayers, but you’ve never listened to people who tried to help you.

SHEEN: You’re right. When you’re in the grips of it, everybody can basically fuck off. But that doesn’t mean I shouldn’t try.

PLAYBOY: Do you remember the day you got off probation?

SHEEN: I drove up to Promises, my rehab alma mater, and I talked with my drug counselor, who had done time and was on probation, too. I wanted to talk to another addict about this blessing and about the progress that had taken place. I said, “I don’t have any desire to get loaded right now. I’m really so grateful and so happy to have my freedom back.” When I was in camp and had to wear the Lo-Jack ankle bracelet monitor, I vowed there and then that I would never again do anything to lose my freedom.

PLAYBOY: Do movies get rehab right?

SHEEN: No. It’s bullshit. I saw 28 Days. I don’t remember rehab being like a day camp or being that funny. Rehab is a dumping ground. It’s a big landfill where you go to unload all your shit. You kind of pick through what’s worth keeping and fixing, reassemble some of the pieces and hopefully move on. Of the 20-some people in my original group, only one other person I know for sure is sober.

PLAYBOY: So what does that say about rehab?

SHEEN: It says more about the disease, how insidious it is. It’s the only disease that tells you that you don’t have it. Rehab is a motherfucker, especially if you’ve had any kind of life where you’ve been the man. Suddenly you’re in a place where there’s no special treatment. You’re equalized.

PLAYBOY: So now drugs are out, drink is out. How about sex?

SHEEN: [Laughs] Of course not. I got sober, I didn’t get stupid.

PLAYBOY: Just curious: How well were you able to function sexually on cocaine?

SHEEN: I was never shut down by the drugs; that was my problem. Cocaine was an aphrodisiac, it wasn’t a cancellation element. I think that was a bit of a curse. Anybody else would say, “What do you mean? You did an eight-ball and had sex all night?” I’d be like, Yeah, didn’t you?

PLAYBOY: And the women were easy to come by?

SHEEN: Yeah. But for every perk, there’s a pitfall. For every free meal, there’s a tabloid story. For every girl who sleeps with you, there are two who don't—and not until the end of the night, when they’re alone with you and back at your place, do you realize they had it planned from the get-go.

PLAYBOY: You didn’t expect to get lucky every time, did you?

SHEEN: No. But they could have told us that at the bar, before we left with them, instead of at three A.M., when everybody else is gone and the options are done.

PLAYBOY: Can we clear up a few Charlie Sheen rumors?

SHEEN: Shoot.

PLAYBOY: Is it true that you hired hookers and had them dress up as cheerleaders?

SHEEN: Total bullshit.

PLAYBOY: Five women in one bed at a time?

SHEEN: True, but it happened only once. It wasn’t a habitual thing.

PLAYBOY: Did you have them laid out in a pentagon?

SHEEN: [Smiles] No, it was just the end of the night and everybody had split. It was me and five girls, and I said, “Well, I’m up for it if you girls are.” They’re like, “Yeah, right.” That was a challenge, so I went for it. I was with one at a time with the other four watching. It was a little uncomfortable, actually. I think I said, “Can you guys just look the other way until it’s your turn?” I wouldn’t recommend five at once. There’s just not enough guy to go around.

PLAYBOY: Where do you normally draw the line?

SHEEN: At two. Even with two, somebody’s always jealous. Even if it’s their idea, someone comes away pissed off. Something happens and you spend the rest of the night apologizing for something they initiated. A lot of times you’ll be with your steady and she’ll invite a girlfriend; they’ll get a couple drinks in them and say, “Hey, whaddya think?” Before you know it, you’re into it. Then you pay more attention to one or the other and there are problems. Two women is a big guy fantasy that looks better on paper.

PLAYBOY: Do you think you’re a good-looking guy?

SHEEN: From some angles, in certain lighting. I wasn’t dealt a terrible hand. I don’t think I’m a romantic sex symbol, but I think I’m ruggedly handsome.

PLAYBOY: Is it true you and a friend took a World Sex Tour?

SHEEN: [Laughs] Which one?

PLAYBOY: Amsterdam. You and he did separate sides of a red-light-district street.

SHEEN: Yeah. Me and Jo-Jo [chuckles]. We set a goal for the one night, and we hit it. Ten each. He took one side of the canal, I took the other. Little single rooms, with women sitting in the windows. You walk up, look through the window, go inside, they pull the curtain and, you know. We left there very tired.

PLAYBOY: How did you manage to maintain your stamina?

SHEEN: I was doing a lot of amyl at the time, and that tends to get the sex thing going. Amyl and Heineken: the Amsterdam combination. Jesus, what a nightmare. You can stay hard, but you’re shooting blanks after a while. Then it becomes about approaching the number. We said 10 each and you’re on eight, and you’re going, I need some fucking pasta or steak or something. Fuck it: Heineken, amyl—that’s my dinner. Then you get to nine. We didn’t want to leave there saying, “We got 17 but we aimed for 20.” It was ridiculous.

PLAYBOY: What was it like Stateside, being young and hot in Hollywood?

SHEEN: It was radical. It was perfect. It was anything you wanted it to be.

PLAYBOY: For instance?

SHEEN: You can go to the best restaurant in town with no reservation, at peak mealtime with seven friends, and say, “We’re hungry.” Then you could leave that meal, call a guy on the way to the airport to fire up a jet to take you to Vegas, go to a casino with nothing—no wallet, nothing—and talk a casino manager into giving you a $50,000 line of credit.

PLAYBOY: Did you do that often?

SHEEN: Not too often, but it was never dull.

PLAYBOY: Where did you hang out in Los Angeles?

SHEEN: Mostly on Sunset, either the Rainbow or On the Rox. I always made friends with the guy who ran the club, because then you could stay after hours and drink. Then there was always a party that went to somebody’s house in town afterward, or you’d wind up in a hotel somewhere near the point of origin—with your select group of friends. You’d tell all the other knuckleheads, “I got to get some sleep, I got to do something in the morning” or some lie, just to get them off your trail. Then you’d settle into phase two or phase three or phase four, however deep you were going. The point was just to seek entertainment on all levels—women, drugs, rock stars. I always wanted to hang out with rock stars because they brought a different element.

PLAYBOY: Were they more or less debauched than you?

SHEEN: At first, more; later on, less. One of my fondest memories is when Slash, from Guns n’ Roses, sat me down at his house and said, “You’ve got to clean up your act.” You know you’ve gone too far when Slash is saying, “Look, you’ve got to get into rehab, you have to shut it down. You’re going to die.” He’s a terrific guy and I love him—he’s a buddy of mine—but I had to step back from that situation and go, “Yeah, but you’re Slash. Whaddya mean?”

PLAYBOY: How far gone were you when he said that?

SHEEN: We’d been up for about four days. But I still heard him because a part of me was saying, “This isn’t as much fun as I thought it was going to be. Something’s missing.”

PLAYBOY: Where did your appetite for self-destruction come from?

SHEEN: A good question. It came from a long time of wanting things I couldn’t have, like women and money and access. From when I was 10 to about 16 I saw other people satisfy those appetites, and I wanted to be not just along for their ride but driving the car.

PLAYBOY: What others?

SHEEN: The group I ran with, the Brat Pack. Emilio’s friends. The St. Elmo’s Fire and Breakfast Club crowd. They had all pretty much hit when I was still auditioning and struggling and wasn’t really getting anywhere.

I got tired of girls coming to me to get to them. We’d be at a table at the Hard Rock and they’d get all the attention; all I got was the waiter telling me what the specials were. I so desperately wanted to be Mr. Somebody: “Thanks for coming back, Mr. Sheen. It’s good to see you again.” Instead, I was the little brother, included to a point, but there was always a time for the youngsters to vacate.

PLAYBOY: Makes sense if you’re 10.

SHEEN: Or 11,12,13. “Go to your room,” or, “We’re going to drop you off now. You’ll hear the great story tomorrow.” I got tired of waiting. I wanted to be telling the great story. I just didn’t know one day I’d have so many to tell [smiles]. Seriously, I guess I just wanted to be accepted, liked, loved. I wanted respect.

PLAYBOY: Did not being the center of attention make you angry?

SHEEN: Yeah. I wanted to eclipse them all, invite them to my parties, take them on my private jet, introduce them to my women and give them my drugs. And when I hit, there was no montage-like transition into it. It was overnight. Suddenly, I did a movie, Platoon, that everybody went bananas for and it won Best Picture. Everything I thought I wanted became available.

PLAYBOY: Is everything you got what you really wanted?

SHEEN: Sure. Fame is empowering. My mistake was that I thought I would instinctively know how to handle it. But suddenly when it’s you, you realize there’s no manual, no training course.As much experience as you might have had hanging out with the people who are “in,” until it’s you, you can’t know. It’s like trying to explain to somebody what it’s like to have sex the first time. Or asking Hank Aaron what it feels like to hit a home run in front of 50,000 people. Eventually, any plan or illusion I had about how I would deal with fame evaporated rapidly, because I took it a little far, I think. Just a tad [smiles].

PLAYBOY: And how did that affect you professionally?

SHEEN: Fame is a fickle mistress. It’s very deceiving. It looks really bitchin’ from the outside, and then you get it and it’s very confusing professionally, socially, emotionally. It’s confusing because you’re so worried about how you’re perceived. A lot of my exploits were guilt-driven, shame-driven. I would hang out with the lower-class individual and try to give away as much as possible, because on some level I felt like I hadn’t really earned all I had, and when was everyone going to find out? When would the curtain be yanked back? And all this because one day I was a working actor, just trying to pursue something I enjoyed and trying to make a living, and the next day I was a commodity.

PLAYBOY: Surely that can’t have been a complete surprise.

SHEEN: No. But it was terrifying. Suddenly they’re telling you, “OK, you’ve proved yourself to a point, and now, with this next picture, we’re banking on you to validate our investment.” You go to the set with a different view of your responsibilities, and sometimes it gets overwhelming.

PLAYBOY: And you handled it by—

SHEEN: Just drinking it away.

PLAYBOY: What kind of advice did you get from family and friends?

SHEEN: I got advice, but there’s a big jealousy factor, so you don’t know what advice to listen to. You don’t know if people are trying to sabotage you or if they genuinely want you to consider your options. Is he telling me to do that because if I fuck up, he’ll look better?

PLAYBOY: Which was it?

SHEEN: Abuse-fueled paranoia. As kids we’re not taught how to deal with success; we’re taught how to deal with failure. If at first you don’t succeed, try, try again. If at first you succeed, then what? We grow up with our fathers talking about walking to school in the snow, uphill both ways, and of wearing the same socks for 10 years while delivering the newspaper for half a penny a month, eating chicken bones and cat hair. We’re raised to believe that you’ve got to work hard for what you achieve. Then you work hard for a while and suddenly you’re not working as hard and you’re achieving more. You start to wonder. It’s no longer so much about the work as it is about the box office and the reviews and the premieres and the premiere parties and the nonsense. It’s confusing.

PLAYBOY: What confused you most?

SHEEN: [Pauses] In the end it was how I went from making multimillion-dollar deals on movies and fucking Playmates to being unemployable and fucking a, um, five-months-pregnant Mexican whore with cesarean scars, in a bar in Nogales. [Pauses] Forget it. I’m not going to tell you that story, but when you go from one end to the other, you have to pause and wonder what went down between those two points.

PLAYBOY: Any answers?

SHEEN: I still don’t have all the answers. To tell you the truth, I’m more interested in what I can do next than what I did last. We’ve talked about a lot of psychological stuff, and, frankly, I’m not all that certain about any of it. Uncertainty is a sign of humility, and humility is just the ability or the willingness to learn.

PLAYBOY: You grew up with Sean and Chris Penn and Rob and Chad Lowe as friends. Were you neighbors?

SHEEN: The Lowes lived about six houses away and the Penns about three miles away. We all went to the same school and lived in the same neighborhood. I met Robert Downey Jr. in high school; we had biology together in the tenth grade. I met Chris Penn in the third grade. Sean is the best actor of our generation, hands down. And he’s only getting better—and it pisses me off [laughs].

PLAYBOY: What’s his secret?

SHEEN: He brings a reality to his work that’s beyond what is required, and I think it takes the audience to another place. He tortures himself doing it, but God bless him, because that work exists forever. It’s educational, watching his stuff. He teaches us about taking risks and about letting go of self, of celebrity, of ego and all that crap we hang on to in front of the camera. Sean just says, “That’s not what I’m here for.”

PLAYBOY: You all made amateur films together, as kids. Super-8s. Anything still stand out?

SHEEN: A film Sean directed, Rooftop Killer. It was about an assassin. We were short on actors, so I played the assassin. It was basically a reason to get to a very violent ending, and to use blood bags and blanks.

PLAYBOY: Did it seem weird growing up with a dad who made movies?

SHEEN: For a while I didn’t think there was anything unique about it. But then I’d see how people reacted to him in public, and as I got older it seemed a little strange. His time was always strained or in demand. My mom has been the anchor of the whole group. She’s really the brains behind the operation. A very smart, strong, sincere, compassionate lady as we traveled the world, living in hotel rooms and watching Dad make movies.

Whenever Dad would talk about a job, the first thing we would say is, “Where does it shoot? Where are we going?” I credit him with keeping his marriage and the family intact by always saying, “I’ve got to have plane tickets for the whole family.” Yeah, he kept us out of school, but school comes and goes. Family is forever.

PLAYBOY: Did you ever want a normal childhood?

SHEEN: What is a normal childhood? We weren’t rich, we were pretty middle-class. My dad survived from job to job; with him taking care of so many relatives, he couldn’t save any money, really. Sometimes we’d move into a new house, for six or eight months, with no furniture, just sleeping bags. Even that didn’t seem abnormal. My parents went through a vegetarian phase, a nudist phase—things that didn’t seem strange until you got to school and everybody else’s lunch boxes were filled with brand names, not health-food shit. There were always interesting people at the house: guru types hanging out, people of advanced intellect in some religion or form of yoga or political sphere. My parents always sought new teachers to better their intellect and awareness.

PLAYBOY: How much did your family talk about acting?

SHEEN: Actually, it’s the last thing we talk about when we’re together. But now we all have to own TiVos so we can watch my show and Dad’s. My sister Renee is on West Wing, too. She’s Miss Landingham’s assistant. They don’t give her enough to do, but she’s really good. I get her an audition here and there, but I won’t get her a job. I just don’t believe in that.

PLAYBOY: Like your father, who didn’t help out with you and Emilio, either.

SHEEN: Right. And we never asked. I knew early on that it wouldn’t be real, that it wouldn’t be earned, which is the one thing he’s always stressed: earning things so you own them. I think what drove me insane for a long time is feeling like I hadn’t earned most of what I achieved because it came so fast.

PLAYBOY: What kind of example did your dad set for handling career and success?

SHEEN: I saw him handle it, I saw him mishandle it. I saw him shy away from it, I saw him embrace it; want it more than anything in the world, hate it more than anything in the world. That’s not much of an example from which to take any kind of feasible approach. And then it almost killed him. He almost died of a heart attack in the middle of making Apocalypse Now, at the time the biggest movie of his life. As an example, it doesn’t make you want to jump into that business.

PLAYBOY: Were you there when the attack happened?

SHEEN: I was Stateside when he had it, but we flew back to help him rehabilitate, all the kids.

PLAYBOY: How long did you spend in the Philippines?

SHEEN: On and off, eight months.

PLAYBOY: Laurence Fishburne, who was in the movie, was young at the time. Did you guys hang out?

SHEEN: Yeah. He borderline introduced me to pot. He and Emilio were going to the dompas, the Philippine whorehouses. In fact, Larry wore a T-shirt on the set that said DOMPA U. He was a graduate. But as usual, though they’d let me have a little grass, at some point they’d send me back to my hooch. I was 10 and turned 11.

PLAYBOY: Why did you choose to go by the Sheen name instead of your real name, Estevez?

SHEEN: Emilio had already used Estevez, and I’d always been a Charlie as opposed to a Carlos, which is also my real name. I just thought Sheen had a better ring to it. A little more Anglo. And I thought I should keep the name going after Dad was gone or retired or both.

PLAYBOY: You’ve complained that after doing 50 movies people still only talk about Platoon and Wall Street.

SHEEN: It’s like they’re the same movie. That Oliver Stone film you did, Platoon-Wall Street. That’s how it sounds.

PLAYBOY: At one point Oliver Stone offered you the role of Ron Kovic in Born on the Fourth of July. How did you feel when Tom Cruise got it?

SHEEN: Disappointed. Hurt. Oliver took me to dinner with Ron a few times, and we started talking. He said we were going to have a relationship like Scorsese and De Niro, and that this was the next movie. He said Al Pacino wanted to do the movie, De Niro wanted to—everybody wanted to—and “I’m going to give you this movie.” I said, “Wow, this exciting.” There were some rewrites to be done and then he was going to Cuba and couldn’t be reached, and, “I’ll call you when I get back.” I didn’t hear from him long past his return date. Then Emilio called me and said, “Dude, I’ve got some bad news.” I thought, Fuck somebody died. He said, “Are you sitting down? Cruise is doing Born on the Fourth.” I said, “Oh fuck, wow.”

PLAYBOY: How pissed were you?

SHEEN: I wouldn’t have cared if Oliver had called me personally, based on what we’d been through. We fought two wars you know. But here was a crucial point for both of us, and he couldn’t even call me and say, “I’ve changed my mind. I’ve made a mistake. I’m going with Tom. That I’d respect. I’m a firm believer in you can’t lose something you never had, but I kind of had it for a while. So yeah, I was very disappointed. But at least it went to a capable actor who did a phenomenal job. Nothing is worse than getting a job, and then it goes to some schmuck who pisses all over it.

PLAYBOY: How badly did it hurt your relationship with Stone?

SHEEN: That was kind of the end of it. I still think he’s a brilliant filmmaker. I’d love to work with him again, and I think the timing is good for us to have a bit of a reunion at some point.

PLAYBOY: You’re serious?

SHEEN: Of course! He’s Oliver Stone [chuckles]. I might have been pissed, but I’m not stupid. He’s still revered as a genius and I’m in the middle of a comeback. The two of us hooking up would be really interesting.

PLAYBOY: After you got sober, you made Rated X, a Showtime movie about the Mitchell brothers, the adult-film entrepreneurs who, among other things, made Behind the Green Door. Emilio directed and played Jim; you were Artie, the self-destructive brother, who eventually died. Why get sober and then do a movie that, in a sense, plunged you right back into that world?

SHEEN: I saw the opportunity as no coincidence, again. There was a reason my first substantial role after rehab was to play a maniac whose personal story ended badly. I knew what it was like to go to those dark places and I got to go home every night after shooting with the reminder that I don’t have to live like that anymore. I played a guy who died as a result of his abuse, so any time I even began to think, Good God, what am I missing, that thought was replaced with, I’m playing a dead man. That’s a gift. It was like a big overcoat I put on when I got to work and then just took off afterward.

PLAYBOY: Your dad urged you not to do the movie. How hard did you have to work to change his mind?

SHEEN: Not much, because while he yelled at Emilio about it on the phone, he talked rationally to me. He was like, "Are you sure? I mean….” He was picking my brain. Then he’d call Emilio and say, “You motherfucker, you’re going to lead him back into the pit of insanity, and it’s going to be your fault! We’ve all worked so hard and he’s worked so hard.” I would only hear this secondhand, from Emilio. But at the end of the day, my dad had confidence. The day we filmed a party scene in the office, with girls and blow and drinks and all that weirdness, it was my actual sobriety date. My first anniversary.

PLAYBOY: You and Emilio were estranged for years because of your substance abuse. Is it poetic justice that his character kills your character in the movie and, symbolically, gets to kill the old Charlie?

SHEEN: Interesting. We thought about swapping roles for about 10 seconds and realized it would be a lie. I never thought about that last bit. That’s pretty radical.

PLAYBOY: And now the new Charlie is on Spin City. How did that happen?

SHEEN: After I got out of rehab I hired a couple of managers—my first. They asked me what I wanted and I said one word: respect. Not a jet, not a big movie, respect. Next thing, they said Jeffrey Katzenberg from DreamWorks had called, and would I come in. I ended up doing Sugar Hill, a pilot for Gary David Goldberg, who also produces Spin City. It didn’t get picked up, but I moved on. Then I was watching the Golden Globes with my friend Adam, and we were talking about Mike Fox being sick and leaving the show. As a joke I said, “They’re probably going to call me to replace him.” Adam said, “Yeah, right. If you get the job, get me a job.” Two days later, I was driving back from a voice-over I did for CNBC.com, and they called for me to replace him.

PLAYBOY: Your reaction?

SHEEN: Be careful what you wish for. I asked for 24 hours. I called my parents, I called my brother, I called friends. I called my therapist and my drug counselor. Everybody was thumbs-up.

PLAYBOY: It seems that lately, from Rated X to Spin City, your career has given you opportunities to if not actually repudiate your former life, then at least confront it publicly. Is this your public penance?

SHEEN: To a degree, sure. It’s my public Antabuse. Being on Spin City is a win-win situation for me. If the show doesn’t work, they can’t say I didn’t take a shot. I can say the show lost its primary component, America’s favorite dude. I stepped in and it didn’t work? Fuck off. If it does work, then I’ve come into an impossible situation.

PLAYBOY: If the show results in a big comeback, can you handle it?

SHEEN: I think so. I have the advantage now. I’ve got more knowledge and more experience. I’ve got volumes on how not to behave. I’ve got more information now than a guy should have at my age. My priorities are totally different.

PLAYBOY: This time, will you believe that you deserve success?

SHEEN: This time I’ll know I’ve earned it.