Charlie Sheen Roast-Mortem: Jeffrey Ross Live From the Actor's House (Exclusive)

Charlie Sheen, Jeff Ross - SPLIT - P
Comedy Central; Getty Images

In an exclusive report for THR, "roast master general" Jeff Ross describes the scene at Sheen's house on Monday night, (“morbid,” “odd,” “totally awesome”) where the guest of honor screened both "Two and a Half Men" and his Comedy Central roast with friends Jon Lovitz, Kate Walsh and Steve-O.

Because I'm a comedian, I work nights and almost never watch television. However, last night I sampled the popular sitcom Two and A Half Men for the very first time. In case you haven't heard, this particular episode included the untimely death of the lead character by a moving train; and the subsequent introduction of a new lead played by the handsome young movie star, Ashton "Jesus Christ" Kutcher.  Sitting beside me offering running commentary while chain smoking was the actor Charlie Sheen, who you may have also heard, used to rake in 1.8 million per week as the original star of that show before he got fired for acting like a schmuck.

So I was really surprised when Charlie invited me over to watch the season premiere of his old show followed by the world premiere of his Comedy Central roast. Only about a week earlier I had stood at a podium dressed as Colonel Gaddafi and fired off a barrage of insults right to his face, like: "Charlie, if you're ‘winning,’ then this must not be a child custody hearing.” And, “The only time your kids get to see you is in re-runs. Don't you want to live to see them take their first twelve steps?"

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Now, I've roasted some badasses before, but none have ever asked the roaster over to their house to watch the edited broadcast. Usually if a celebrity chooses to re-live this onslaught of putdowns, they do it surrounded only by next of kin and possibly a team of psychiatrists.  After all, hearing the meanest comics in the country say the cruelest things they can think of at your expense is tough to endure even once -- so why relive it in the comfort of your own private screening room?  But once again, Charlie proves he's different.  In fact, a week earlier at a pre-roast dinner, Charlie himself stood up and declared no topic to be off limits. Clearly this is a guy who likes to play rough.

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I got some insight into Charlie's personality when I showed up during the last leg of his My Violent Torpedo Of Truth: Defeat Is Not An Option tour. When the crowd started booing and screaming for refunds, I would walk out in a hazmat suit because I "heard there was a bomb scare." Then, a podium would roll out and I would proceed to roast Charlie for pretending to be a real comedian. "Folks, Charlie Sheen is to stand-up what Larry Flynt is to standing up;" “Two and a half men was also the amount of people left in the theater after intermission;” “Even Bernie Madoff saw your show and asked for his money back."  I did this in eight different cities and got meaner in each one. Charlie took it like a champ. He may not have "Adonis DNA," but he definitely has skin thicker than an elephant.

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So people ask me: “Is he really that crazy?” Yes, I believe he is. He's certainly not above having three tour buses and a Tampa police escort pull over at four am if he wants a popsicle.  I can also tell you that like his character in Wall Street, he's obsessed with making and spending grotesque amounts of money.  Except for his kids and baseball, money is Charlie's life. Collecting old watches and young women can be costly. So the very idea of watching him take in the sight of some pretty boy trampling through his TV house and taking possession of his real-life salary was both painful and fascinating to witness.

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So here’s how it all went down: everyone gathered in front of a flat screen in Charlie’s living room. He was surrounded by old pals and recent roasters as the opening sequence of Two And A Half Men began. We were all a little tense as Jon Cryer stood in front of Charlie's bowling shirt and offered up a eulogy for Charlie's character, named Charlie. The funeral scene included cameos by a bevy of beautiful actresses who had portrayed Charlie's love interests over the years.  As each woman spoke, Charlie nodded subtly to himself, as if checking off their names on a "need 'em, got 'em" checklist. A brief walk-on by my pal John Stamos seemed to take Charlie by surprise, but played well with us all -- especially when Stamos admitted to having gay sex with Charlie. It's almost like the roast had started.

Charlie seemed genuinely thrilled to see Holland Taylor and Angus T. Jones hitting their zingers like old times.  At one point Charlie smiled fondly and mumbled something about an "epic line reading" from his TV mom. Charlie laughed at the better jokes and rolled his eyes at a fart joke. I noticed there was an open spot on the couch next to Charlie so I grabbed it. 

I whispered, "How do you feel?” 

"Odd," he answered.

Moments later it got even odder when Jon Cryer began talking to an urn full of Charlie's ashes. "Oy, this is morbid," I blurted out. Charlie looked at me to make sure I wasn't kidding. "Yes, very fucking morbid," he said.

I must admit I didn't really pay too much attention to Ashton's big entrance, because I couldn't take my eyes off Charlie.  I figured any second he would lunge at the TV or stab somebody with a fork.  But I heard the laugh Ashton got and Charlie seemed impressed. "Wow. They gave him a fucking entrance like a movie", he told us.  I guess Charlie figured that if he had to get replaced -- better to have it done in a big way by a good guy.

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As the episode's credits rolled away, I saw Charlie take a deep breath. He looked almost relieved. As if he secretly realized that this night was some sort of public punishment for his erratic and scary behavior over the past year. Perhaps it's even a small price to pay for all the fun he's had in his life.

His subdued interviews with Jay Leno and Matt Lauer last week were described as "contrite." I also heard similar sentiments about his surprise appearance on Sunday night's Emmy Awards. More than one Charlie supporter lamented to me why he submissively wished the cast and crew of Two & A Half Men a wonderful season without him -- instead of using the opportunity to land a big joke and prove why he was once the highest paid and most popular guy on the boob tube.

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As I sat there in his sprawling mansion eating my third helping of lobster ravioli, I actually started to feel sorry for the guy.  What I always found interesting about him was that he never apologized for his lifestyle. He's the one celebrity who messed up his life and career -- yet still refused to go on the Oprah apology tour and beg for forgiveness. Now he suddenly seemed in a headspace somewhere between docile and brain dead. I immediately thought of the tall quiet Native-American "Chief" from One Flew Over The Cuckoo's Nest and scanned Charlie's temples for a lobotomy scar.

As if watching his show go on without him wasn't torture enough... Charlie's long time assistant Rick changed the channel because the comedy portion of the evening was about to start.

Charlie moved into his screening room and parked himself in a dark corner. My fellow roasters Jon Lovitz, Steve-O, and Kate Walsh followed him in and sat amongst Charlie's friends and all the top people at Comedy Central. We all smiled broadly as Roastmaster Seth Macfarlane introduced an inspiring and funny montage of Charlie's film and TV work. This roast was no lifetime achievement award, but it was still nice to be reminded how talented Sheen is before the barbs started flying. Even Charlie was smiling when he saw himself as a young crew-cutted recruit in the Oscar-winning film, Platoon.

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Macfarlane went on to read Charlie's anticipated obituary. Jon Lovitz told the audience that Charlie did enough coke to "kill two and a half men." However, it was the classy dramatic actress Kate Walsh who was the first roaster to mention Charlie's kids during her performance and it seemed to hit Charlie even harder now than it did at the live show.  She said, "You know what's amazing? Despite all those years of abusing your lungs, your kidney, your liver... the only thing you've had removed is your kids." Charlie on screen and Charlie in person both mouthed the word "Wow" at the same time. 

During the commercial break, Lovitz lowered the TV volume so I could ask Charlie if he was okay. "Terrific. This is totally awesome," he deadpanned. 

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The night only got rougher from there.  It was my turn to pound him about his tour, his whores, his movies, his nostrils, and his ex-wives “… And I see the lovely Brooke Mueller is here tonight.  She's not very bright -- unless Charlie is throwing a lamp at her." Too soon? Nah. Too real? Probably.

After me, came dirty poetry from Mike Tyson, libelous jokes from Anthony Jeselnick, brave and sexy jaw-droppers from Amy Schumer, tough love from Steve-O, fatherly advice from William Shatner, and a scathing clean up spot from professional race riot, Patrice O'Neal.

As each roaster finished, they got a big round of applause from Charlie. Still, he seemed to laugh the hardest at his own rebuttal. As if he couldn't believe he was getting away with this insane victory speech. In the end, he declared to the world, "I'm done with the 'winning,' because I've already won. This roast may be over, but I'm Charlie Sheen, and in here burns an eternal fire. I just have to remember to keep it away from a crack pipe." Everybody in the screening room was laughing hard. I'd never seen a man of the hour deliver such a powerful rebuttal. Afterwards, Charlie hugged everybody as they left and lit himself a moist Cohiba. I watched him take a puff and smile at the sky. Then he offered me one, gave me a hug and thanked me for "everything.”

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As I puffed my way home, it suddenly hit me like a lamp flying across one of Charlie's hotel suites.  Our comedy intervention had cured him. Our verbal beat down was so vicious and real that it actually humbled the guy back to normal. The tiger blood was suddenly transfused. The warlock was dead and buried. The Rock Star From Mars was now just another character on Charlie's long resume. Charlie Sheen the nut job is finally ready to be Charlie Sheen the actor again. Last week's sober-sorry guy routine was only a transitional phase. Just give Charlie a few months. He'll find another great role he can sink his broken teeth into. This guy is so ready to come back big, it's not even funny. 

Once again, roasting saves lives.


Jeff Ross

Jeff Ross' book, I Only Roast The Ones I Love: Busting Balls Without Burning Bridges, is currently out in paperback.