Charlie Sheen's Naughty, Bawdy Joke Man Reveals Surprising Secrets of the Tour (Exclusive Q&A)

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Jeffrey Ross

Credited with saving the show, comic Jeffrey Ross reveals how he ended up on the "Torpedo of Truth" tour, the one topic that’s off-limits during the show and how he first had to insult Sheen to get the job.

How does comedian Jeffrey Ross describe his role as Charlie Sheen’s official Torpedo of Truth tour roaster? “I’m like a kid in a candy store,” he says. “The idea that you can roast a notorious figure like Charlie Sheen once is a dream, because there’s so much there. To take it another notch and do it live every night? I’m in heaven right now.”
Ross, known for his Comedy Central putdowns of Pamela Anderson, David Hasselhoff and Donald Trump, has eight Sheen dates under his belt and is scheduled to rejoin the tour in Vancouver on Monday and Seattle on Tuesday. He sat out Saturday's San Francisco show to honor a previous commitment to host an event for the charity Operation Mend.
In an exclusive interview with The Hollywood Reporter, Ross says he considers his 15-minute shtick “a public service” and “a moment of levity” in an otherwise grim, though fascinating, tale of a life lived to the max. It seems audiences agree, as many have commented on Twitter and YouTube that Ross “saved” the near-catastrophic trek, which was seeing walkouts and refund demands at many stops.
“It definitely makes me feel good to hear that,” he says. “Roasting saves lives. Telling the truth through tough love, through backhanded compliments, through harsh insults, it can be really therapeutic and bring people together. That's what I see happening between Charlie and the audience, and also between me and him.”
The Hollywood Reporter: First off, did you know Charlie prior to the tour?

Jeffrey Ross: Never met him. My only connection to him was that we have the same pharmacist, which sounds like a joke, but it's not. I happened to mention that I was joining the Sheen tour for a night, and he said, “Charlie's a customer, tell him I say ‘Hi.’”

THR: So how did you come to join the tour?

Ross: I was reading the press accounts of his shows obsessively. I couldn't stomach the reports that he was bombing. As the son of a caterer, I couldn't bear that the customers were yelling “refund.” So it was sort of haunting me, and by coincidence, I started getting calls from various people involved with the tour, friends who I know from New York like Simon Rex and Bob Maron. It started after Detroit, when they had that awful catastrophic bomb. They were asking if I would come to Chicago, or to Radio City [Music Hall], or Toronto? I was like, “I don't know, this sounds toxic …”
THR: What did they have in mind for you to do?

Ross: They were looking for ideas. They were up all night writing. They asked if I would do a walk-on in Chicago, they wanted me to be a sort of moderator… Then it came around to Atlantic City — my home turf, New Jersey — and they asked again. I said, “If Charlie calls me himself and says it's OK to roast him, and if he can go through that gauntlet, then it will be great.” I had just done this at the Trump roast with The Situation, so I felt like I could sort of step into these "shows,” which are as much a rally or a riot as a roast.  
THR: And he called?

Ross: Yeah. I was at a party that Jimmy Kimmel threw for Howard and Beth Stern, who were in town a couple weeks ago, and at about 11:00 pm, my phone rang. Sheen said, “No holds barred, do whatever you want, rip me to shreds, it'll be really fun … Take the 6 a.m. flight to Philly and we'll see you at Atlantic City by 8:00.” Kimmel was very adamant in telling me I had to do it, because it was a once-in-a-lifetime chance to roast somebody in public -- unedited, unfiltered, no network censorship. By the same token, I had friends who said, “Stay away, Sheen is trouble.” So I knew I was walking into a polarizing environment. But I thought, this is for the audience. These people paid a lot of money for tickets! So I left the party a little buzzed, wrote some jokes until about 4:30 a.m., packed for the night, since I thought I was coming right back, and flew to Philly. I met Charlie about 10 minutes before the show.

THR: Tell us about that initial meeting. Did you discuss how things would play out onstage that night?

Ross: When I landed, I asked the road manager, when's sound-check? When's rehearsal? And he just laughed in my face. So I waited around, had a steak, and about 10 minutes before the show, I met Charlie, who was half-listening to me, half-watching a ball game. I told him what I wanted to do: the first sign of trouble, I'll walk out unannounced. He's, like, “Great.” Then his bodyguard Chuck Zito puts his fist up and says, “Make sure the jokes aren't too mean or you’ll be kissing these knuckles.” That was when I thought, “What have I gotten myself into? This is beyond show business, it's something else.”

THR: How did that first show go?

Ross: I let him sweat it out for a good 30 minutes, then he started getting a little choppy and someone yelled out, “I want a refund!” We didn’t have a cue or anything. I walked out in a hazmat suit, pulled the mask down, and said, “Charlie, I heard there was a bomb scare, I got here as quick as I could. These people paid for a show, they deserve a show … it's a comedy intervention.” Because that’s what was driving me crazy: He was billing it as a comedy tour without being a comedian. You can see why comedians were not supporting it; they were insulted. And it's tough to insult a comic.
So I just laid into him -- the meanest things I could think of on a day's notice: “You call yourself a Warlock from Mars — maybe you are, but you're not a comedian from Earth;” "If you're winning, then this must not be a child custody hearing;” And my favorite: “Charlie Sheen is to stand-up what Larry Flynt is to standing up.” At the end, he hugged me and asked me to do the next show at Foxwood’s. Since I already had the weekend off, I was on the east coast, I figured I'd do both shows and then be halfway to New Jersey to see the family on Passover. It was the oddest mix of happy accidents imaginable.


THR: Has any topic been deemed off-limits?

Ross: Only one thing: I had a joke about Charlie living with two porn stars, and Natalie [Kenley], his current goddess, said "You know, I'm not a porn star, so maybe you don't have to say that." It was the only adjustment they asked me to make and I thought that was adorable. And in the last few shows, Charlie’s been roasting me back. He says, “What a week, we lost a goddess and gained a lard ass” and “Jeff, how do I lose you in a custody battle?”
THR: Who goes to a Charlie Sheen show?

Ross: It's a combination of people. There are those looking for a morale boost and see him almost like a Tony Robbins figure -- he's a guy who doesn't walk the plank. With all his troubles, he didn't go on the “I found Jesus” circuit, he didn't go to Oprah and say “I’m sorry,” he doesn't apologize for who he is. He's different and people are responding to that. The other part of the audience is the voyeuristic weirdoes who wanna see a train wreck, and I feel like I’m playing to both of them.
THR: What’s the split?

Ross: Like 70 / 30, favored to the real fans. And forget what you read in the press, they are not walking out, at least not the shows I’ve been on. They are lining up hours in advance, they’re in the front row wearing “Duh, Winning!” T-shirts, they're waiting outside for his bus, they’re showing their boobs and they're screaming “Tiger Blood.” It's sort of like a motivational speech.
THR: Sounds like a rock concert …

Ross: The shows are very punk rock --it's almost like the Sex Pistols, where he just doesn't give a f--k. But when we get off the plane, I feel like we're Led Zeppelin in the 70s -- the abundance, the extravagance… we have shrimp and lobster after the show, there are crazy fans and women that want to meet us everywhere we go. It's all Ritz Carlton and Four Seasons… There’s a little bit of General Patton mixed into Charlie, he seems to relish having 24 people on the road…. We have a private jet, three buses and a submarine … but no drugs. I can't say the same for the audience.
THR: In the eight shows that you’ve roasted Sheen, what’s been the best moment for you?

Ross: When a guy walked onstage with a Sheen/Ross for President/Vice President T-shirt that he made himself. That’s when I realized that, not only did I drink the Kool-Aid, I was not there for completely unselfish reasons -- I was indeed having a blast through all this mishigas. I'm gonna hate to see it end! How do I go back to the farm after I've seen Broadway?
THR: And your worst?

Ross: One night when Charlie wanted all his buddies to come on the plane with us to Tampa, which meant the crew, including the road manager, had to take the bus. So we land, there's a bus and two SUVs waiting for us on the tarmac in Tampa, we all load in and drive eight minutes to a hotel. Charlie leads the way and we soon realize we’re at the wrong hotel at 3:30 in the morning. We all laughed about it.  
THR: Of the stories that Charlie tells during his portion of the show, has anything blown your mind?

Ross: His life experience is uncanny. For a guy who's in his mid-forties, it sounds like he's an 80-year-old looking back, which is fun to listen to. I get out of the way of the salacious stuff. I come up to bring some levity and take everybody on a jokey vacation for the rest of the show.
THR: Do you see this tour continuing beyond these dates?

Ross: I can't imagine him doing more. Then again, the one thing I've learned with Charlie is, you can't predict what he's gonna do.
THR: Do you think he should go back to Two and a Half Men?

Ross: I see that the fans want it. I feel like he had some closure last week where he sort of put it behind him. Our show in Denver was like a wrap party for Two and Half Men. But I've never seen the show so I don't know Charlie from Two and a Half Men. I know Charlie from his movies. There’s a joke I do, where I say to him, “No one could ever take away your incredible movie career -- Platoon, Wall Street Platoon, Wall Street.” In my opinion, his next step should be to get back in touch with his acting roots. He's very intense and that probably works better on film than television, although obviously there’s a big appeal for him to be on television. He's drawing thousands of people in every city. He was the highest paid actor on TV, and whatever he chooses to do next, I can tell you firsthand, there’s a huge mass of people waiting to support him. I think he should do a sitcom with me.

THR: What’s the pitch?

Ross: Brothers who meet in an orphanage -- one who speaks the truth and the other who also speaks the truth but through insults.
THR: As a Jew, do you find some of his comments about Chuck Lorre to be anti-Semitic?

Ross: If he is, being anti-Semitic is probably No. 5 on a list of things that are wrong with him. I'm not on the tour to defend Charlie Sheen, I'm there to roast him and I'll leave it that. I've never met him before, he's not my friend, it's a marriage of convenience, in a way. Do I find him charming? Yes. Is he sober? Yes. He’s also smart and pretty crazy -- he’s not beyond having three busses pull over for a popsicle at 3 a.m.... But I don't know the crack-head, I know this guy who wakes up early every day, runs five miles, eats well, treats the people around him great and is trying desperately to get his life on track and his kids back, that's what I see.