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Jon Cryer Reveals the Inside, Insane Account of Charlie Sheen’s Infamous Meltdown

What's it like to ride shotgun with Sheen during 'Two and a Half Men'? For starters, he suggests you find prostitutes after your divorce. And it doesn't end there. Here, THR debuts an excerpt from the actor's candid, funny new memoir, 'So That Happened,' that details Sheen's crazy world of benders, porn, drugs, tantrums and salary negotiations.

This story first appeared in the March 27 issue of The Hollywood Reporter magazine.

To some, he’ll always be Duckie, the unlucky-in-love sidekick from John Hughes’ 1986 classic Pretty in Pink. To others, he’s Alan Harper, the unlucky-in-love brother to Charlie Sheen‘s lothario on the Chuck Lorre-co-created sitcom juggernaut Two and a Half Men, which had its series finale Feb. 19. Now Jon Cryer opens up about who he really is in So That Happened (out April 7 from New American Library), a wry, self-deprecating and funny memoir that covers his 35-year career from getting cast in Torch Song Trilogy on Broadway in 1983 because he looked like Matthew Broderick (who had previously played the role) to being frozen out by Andrew McCarthy and Molly Ringwald during the making of Pretty in Pink to his Emmy-winning run on Two and a Half Men.

Cryer, who turns 50 on April 26, was born in New York with theater in his blood — his parents, David and Gretchen, were Broadway actors. After graduating from the Bronx High School of Science (and a summer studying Shakespeare at the Royal Academy of Arts in London), he shot to fame with Pretty in Pink. Fifteen years of failed TV series and just-misses (he nearly was Chandler Bing on Friends, Mr. Pink in Reservoir Dogs and Daniel in The Karate Kid) followed before he got cast on Men. This exclusive THR excerpt picks up Cryer’s story during the show’s first season and then moves to the second season, when he was newly divorced and Sheen’s marriage to Denise Richards had broken up, and then moves to the drama of the seventh season. — ANDY LEWIS

One day during the first season of Two and a Half Men, I got a knock on my trailer door. It was Charlie — my trailer was next to his — and he seemed panicked.

“Dude! Dude! I need your help.” “Sure thing,” I said and ended the cellphone call I was on. “What’s going on?”

He handed me a heavy shopping bag. “Denise is coming over,” he said, “and I need you to hide something for me.” Oh, boy, I thought. If this is drug paraphernalia …

“Is it legal?” I asked. “What? Yeah, oh, yeah. It’s legal. Hey, thanks.” He left, and I had to look.

By legal, he meant barely legal. The bag was filled to the brim with porn.

Curiosity getting the best of me, I had to find out what kind of porn captivates Charlie Sheen, what decadence frightens him into having me squirrel it away for him. Clowns? Golden-shower pictorials? German scat porn starring Federal Reserve chairman Ben Bernanke? I was prepared for the weirdest, but it really was all pretty tame, some of it just topless mags. Really, if this was the worst I’d have to deal with regarding Charlie’s vices, bring on the bags of porn for me to hide.

Even when I secretly hoped for a sighting of Sheen decadence, as when we traveled to Las Vegas to promote the show by hobnobbing with CBS affiliates from around the country, I was confronted by a pretty grounded, sober married guy. We landed in Vegas, and I was ready to get the Sin City tour from my co-star. Instead, he went to his room and took a nap. We showed up at the party for the syndicated stations, and then Charlie went back to his room to sleep. I watched our director, Jim Burrows, play blackjack.

What happened in Vegas didn’t have to stay in Vegas because it was boring as shit.


When Charlie’s marriage to Denise ended during the second season, both Charlie and I became single at the same time. Which was … interesting.

We’d have conversations, and he’d mention that things were going well for him romantically. “Romantically” is my choice of words, not his.

Then, as if to prove this, he’d show me a picture he’d taken of somebody’s vagina. It was always a perfectly nice-looking vagina, but I would invariably think, “Why just this, and not the rest of the person?”

From Left: McCarthy, Ringwald and Cryer in ‘Pretty in Pink.’ Duckie “was the guy I wanted to be in high school” because of his “swagger and biting wit,” writes Cryer.

And what do you say in that moment? Thank you for that vagina picture? How long have you been seeing … it? Please tell me she was awake?

We talked about prostitutes. He’d said publicly that you don’t pay prostitutes to come to your house; you pay them to leave. He’d thought this through, obviously.

I was in a bad state right after my divorce, and I certainly didn’t feel dateable. I was an emotional basket case. What good was I to any woman I might have interest in? I decided I might as well pay someone for company and certain intimate pleasures so that I could at least get my equilibrium back with the opposite sex.

Charlie suggested a few online purveyors he occasionally used, as this was when prostitution was gaining a foothold on the Internet. He and I had different tastes, so I didn’t go with his exact recommendations, but my forays into prostitution were about as awkward as you might imagine.

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I went with an out-call for my first try, which means they come over to your house. My chosen vendor drove a white BMW and sported a sexy Finnish accent. It was really a very friendly experience, maybe because the act of having sex is quite the conversational icebreaker. The next time, I went to her place, which probably wasn’t really her place. We sat down, tried to make small talk and halfheartedly stumbled into a conversation about recent fluctuations in the stock market. Somehow I ended up spending 25 minutes of my hour helping her with financial planning.

If Charlie’s example of his evening’s entertainment was best exemplified by a snapshot of lady parts, mine would be a picture of me hunched over a table of papers and telling a hot lady, “The real estate boom is building, you need to diversify.”

My first opportunity to dip my toe into the nonprofessional pool of available women came soon afterward. Rich, my trainer, threw a party one night where I met an engaging, beautiful woman — an aspiring actress and comedian — and we hit it off. I asked her out, and before long we were dating regularly. It felt great. I brought her to the set and introduced her to Charlie, who looked at her blankly.

“We’ve actually met before,” she said. “I was a waitress at La Moustache?”

“Right, right,” he said. “Hello. Nice to see you again.”

A few weeks later, I was sitting around on the set with a shit-eating grin on my face and a sense that my life was coming back to an even keel when Charlie strolled over.

“What’s going on? What’s with the smile?”

“Things are going good with Stephanie,” I said.

“Hey, listen, we gotta talk. I’ve been talking to my therapist because I don’t know if I should say anything. I’ve been agonizing about this, dude, really. I … I don’t know how to say this, but … Stephanie and I used to date.”

“Oh?” I said, my grin suddenly replaced by something pursed and worried. “Well, was it serious, Charlie?”

“No, no, not really.”

I could tell he was trying to play this down for my benefit.

I tried to gather my train of thought with this new information. “If I may ask, how did you two break up?”

Charlie said, “Well, I wanted to bring another girl into bed with us, and she was not happy about that.” And then he looked me straight in the eye and with no trace of irony, said, “So heads-up on that.” I went home that night and broke up with Stephanie.

I once dated a striking Dutch singer who sheepishly admitted a few dates into our courtship that she was, in fact, a baroness. She said it the way you might murmur worriedly, “I used to be a Shriner.” Now, that’s endearing. “I used to bang your co-star” — that’s upfront information, ladies.


In late 2009, Sheen’s longtime struggles with drugs and alcohol began to impact his personal and professional lives, leading to his ultimate dismissal from the show.

I had been enjoying Christmas Day of 2009 so much with my family around me that I somehow managed to stay away from all Internet-connected devices. It’s the holiday present that doesn’t announce itself, really. Then, of course, you give in, check a news site and read that your co-star “Carlos Irwin Estevez” has been arrested in Aspen, Colo., for spousal battery [of third wife Brooke Mueller]. Alarmed and freaked out, I texted him: Dude, my thoughts are with you. If you need to talk, give a call; if you’ve got bigger problems, call me when you get back.

Charlie texted back: Thanks bro. Yikes — f— me, wut a bad day … I’m flying home tonite. I’ll try to call over the weekend. Shower rape was bad but the food was okay. Hair and makeup for mug shot got there too late.

He followed that with: And I had same bail bondsman as Kobe. … No joke … 🙂

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I took the sense of humor about shower rape and sharing Kobe Bryant‘s bail bondsman as a good sign, though it seemed pretty clear my friend and colleague wasn’t sober anymore. We exchanged “Merry Xmas” texts, though mine had a question mark, to which Charlie texted back, I’ll take it!

Charlie’s manager, Mark Burg, called me to say that any statement of support I could offer up would be great. I told him I would be happy to but that it sounded like Charlie wasn’t sober anymore, and I hoped he’d get on track again. Situations like this are rough on your sense of friendship and loyalty, because the allegations are serious, yet you know Charlie and Brooke are a drug-troubled pair, and Charlie’s your longtime friend who was proud of his sobriety, but that doesn’t mean he didn’t do something to her, and you should give a woman the benefit of the doubt when she’s been abused, and oh, boy . . .

In February I got a knock on my trailer door one day, and it was Chuck Lorre. I invited him in, and he said, “Jon, can you talk to Charlie? I hear he’s going off the rails.” Chuck himself is a recovering alcoholic and open and honest about it. This was such a sincere plea that I knew I had to consider it. “I can try,” I told him.

The next day, though, Charlie went into rehab, so we never got to have that conversation. Charlie did, however, have a different kind of productive conversation — with Warner Bros. Despite falling off the wagon, a rocky marriage, looming felony charges and possible time behind bars, he managed to secure a massive raise [to $1.8 million an episode], fully three times what I was being paid. I immediately began contemplating a series of well-publicized drunken brawls in retirement homes or possibly leading cops on a destructive car chase just prior to my next contract negotiation.


Charlie didn’t look so good as we started our eighth season in fall 2010: gaunt, pale, sallow, even sweaty occasionally. He started talking to himself. Most of all he just looked thinner, in a not-good way.

His timing started to go off, too. He was rushing lines. Charlie just wasn’t hitting the jokes the way he used to. One time during rehearsals to choreograph the movement for a scene, he asked, “Can I just stand next to this couch?” He wanted to hold on to it for the duration of the scene.

During a week off in October 2010, I was in New York for a birthday party for my mother, and Charlie was there as well, taking time to see Denise and the kids. He invited me to go see the Broadway production of Mary Poppins with them, but I told him I couldn’t. Charlie texted me the next day that the kids had to wake him up 48 minutes into the show and that the family was “ready to bolt.”

I’m not saying Mary Poppins always has a calming, cheerful influence on everybody, but Charlie had his own interpretation of the kind of spoonful of sugar that helps the medicine go down, as I learned the next day when I read about his “booze-and-blow binge” — so described by The New York Daily News — and the “semipro” escort found naked and locked in the closet of his trashed hotel room. I texted him if he wanted to talk, and he texted, Thanks, bro. … Shoulda stayed for the whole Poppins show. … Oops … 🙂

I began to imagine scenarios in which I enthusiastically agree to go to Mary Poppins with him. Then afterward, when he says, “Thought I’d head back to the room with a prostitute, get really f—ing high, decimate the place, then toss her in the closet,” I say, “No, I don’t think you should do that.” Then he says, “You’re right. Let’s get ice cream.” Then everything is better.


There’s a long history in Hollywood of performers with addiction issues being enabled and even abetted by the studios they work for. But on Two and a Half Men, the time had come for then-Warner Bros. honchos Bruce Rosenblum and Peter Roth to get involved. A couple weeks into January 2011, Chuck informed Charlie that at the end of that week’s show taping on Friday, Bruce and Peter were going to meet with him.

This official-meeting shit was the kind of thing that drove Charlie up a wall. Backstage, he was talking to himself and getting madder and madder.

Gabe and Janice, his respective makeup and hair people, were trying to do their jobs while he fidgeted and smoked. He started to get manic as he psyched himself for what he assumed was a meeting of incredible importance.

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It was so tense backstage, I thought he was going to come to blows with someone.

I walked up to him and said, “What are you worried about?”

“All these assholes are gonna come, they’ll spend two hours giving me shit, and I’m just gonna have to nod and say yes. I’m tired of all the bullshit!”

“OK,” I said. “Then do you want to give them a reason right now to give you even more shit, or do you want to buckle down and do the show?”

He looked me in the eye and said, “Yeah, you’re right.”

Things didn’t start smoothly once the show began. We did a scene with the two of us sitting on a couch, and Charlie screwed up every line. He could not remember anything he was supposed to say. It was hard to comprehend what I was seeing because Charlie had always prided himself on getting it done on show night. It was like watching HAL go haywire in 2001: A Space Odyssey.

Mark Samuels, our assistant director who is the soul of diplomacy and quiet competence, said to Charlie, “Do you need a minute?” (Over the years, Mark had acquired a courteous way of answering a frustrated director’s “Where’s Charlie?” query. He’d say, “He’s been invited.”)

Charlie paused, then said, “Wait a minute; just give me a second.” Somebody handed him the pages, and as he went over them, the rest of us were extra­ordinarily uncomfortable. The audience was here, after all.

And then a rather astonishing thing happened. On take two, Charlie completely nailed it. Every beat. Every line. When he absolutely had to focus, he did. It was a strange and impressive thing to behold.

Instead of sticking around after the taping, however, Charlie chose to walk out, still in full makeup, get in his car and have his driver take him home. He left Bruce Rosenblum and Peter Roth just standing by his trailer. And with that, we all accepted that something was truly broken here, that Charlie couldn’t be counted on to even go through the motions anymore. That was the last episode of Two and a Half Men Charlie would ever shoot.


America’s — indeed the world’s — reaction to the meltdown was cacophonous and unsettling. Opinions ranged from righteous indignation to purple-faced outrage. The bellicose underbelly of the Internet was unleashed.

After Charlie gave Chuck’s phone number to a radio host on the air, Chuck received so many death threats that he had to hire personal security.

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The web was boiling with anger about Charlie’s dismissal. Predictably, there were those who were angry because they felt it had been way too late, that his alleged crimes demanded this action long ago, but surprisingly there were also those who felt it was unjustified. An astounding number of people stood up for Charlie, as though people should be able to show up to work rarely, if at all, verbally abuse their co-workers publicly with anti-Semitic slurs, get arrested on a regular basis — as well as abuse drugs to the point where they can barely function — and not have their high-paying jobs threatened. They directed their fury at Chuck but also at me, with hundreds of comments about how I’d betrayed Charlie, that I was a “homely fag” and that they’d never watch a show with me as the lead. As ridiculous and horrifying as those sentiments were, it was impossible for me not to feel their effect.

America’s faceless corporations didn’t acquit themselves particularly well, either. They began clamoring to capitalize on the marketing opportunity that Charlie’s epic flameout was presenting. Ustream gave him a webcast platform to continue his rants in a monetized worldwide fashion. Live Nation immediately offered him millions to go on a stage tour across the U.S., which he christened his “Violent Torpedo of Truth.”

I knew that Charlie, while being a gifted actor and a remarkably smart man, didn’t have the slightest f—ing idea how to put on a live stage show, even when he wasn’t loaded, but I figured he must have at least one person in his retinue of managers and hangers-on who knew what they were doing. Turns out I was wrong. His first few dates resembled exactly what happens when a bunch of assholes throw money at a drug addict to make him dance like a monkey.

A curious phenomenon was bubbling up in the media as well. Entertainment culture had become so stultifyingly repetitive and predictable that Charlie’s antics felt like a breath of fresh air. To some authors, commentators and bloggers — seemingly intelligent people — he was a rebel, a truth teller willing to poke his masters in the eye. They defended his baleful screeds. (I’m looking at you, Bret Easton Ellis.) Of course, Charlie wasn’t those things. He was simply lashing out at the people who told him the party was over. That he was actually just a human being with a monumental drug dependency mattered less to the pundits than his value as something to write about to alleviate their collective boredom. The fact that he could very well be dead soon was not their concern. In fact, it’d just give them more to write about.

Charlie was never an insurrectionary guerrilla fighting the established order. He was a guy who got everything he had ever wanted from it. He even texted somebody at the show once, I think they gave the wrong guy too much money.

From So That Happened by Jon Cryer, to be published on April 7, 2015, by New American Library, an imprint of Penguin Publishing Group, a division of Penguin Random House LLC. Copyright © 2015 by The Niven Company, Ltd.

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