Jeff Ross’s ‘Roast Battle’: Where Nothing Is ‘Off Limits’—Even Barron Trump

Comedian Jeff Ross talks about Roast Battle II, which culminates with a live finale on Sunday night. Plus, watch an exclusive clip from Saturday night’s quarterfinals.

Photo Illustration by Lyne Lucien/The Daily Beast

Joking about 10-year-old Barron Trump can get you suspended from Saturday Night Live, but it just might help you win Roast Battle.

One of the jokes at a taping for the quarterfinals of comedian Jeff Ross’s hit competition show on Comedy Central, which will air its live finale this Sunday night, came from up and coming stand-up comic Frank Castillo. It was directed at his opponent, Anna Valenzuela. “You’re like a Trump,” he told her. “You’ve got the body of Melania, the brain of Ivanka, and your womb is Barron.”

Unlike the controversial Twitter joke from SNL writer Katie Rich, this one did not take aim at the young Trump, but it still invoked his name for comic effect. It was also one of the tamest jokes of the night.

“Nothing is off limits on this show,” Ross tells The Daily Beast by phone a couple of days later, stressing that there’s a big difference between making fun of Barron Trump and using a play on his name to roast someone else. “I think there’s a general sensitivity about children,” he continues, “but at Roast Battle people are much more open-minded and they understand that this is the one place where it’s safe for just about anything.”

And, for the record, he does not think comedy writers should ever be fired for making a joke. “Bad taste is not a crime,” Ross says. “If the joke is clever, I have an open mind to any topic.”

Ross, known as the “Roastmaster General” by comedy fans, has performed at more than a dozen celebrity roasts on Comedy Central, including last year’s Roast of Rob Lowe that featured a disastrous appearance by Ann Coulter. After moving on to roast prisoners and cops in a pair of comedy specials for the network, he developed Roast Battle as the logical next step last year.

More sports spectacle than comedy performance, Roast Battle pits relatively unknown comedians against each other to see who can land more rhetorical knock-out punches in the span of about 10 minutes. Ross judges the tournament-style competition along with celebrity guests like Patton Oswalt and Snoop Dogg. Before each round, the show’s host Brian Moses leads the live audience in a chant of “Battle! Battle! Battle!” that feels like something out of a WWE match.

“I think we borrow from wrestling, I think we borrow from UFC, I think we borrow from sports in general,” Ross says, noting that Sunday’s finale will air live and unedited like any other major sporting event. “Comedy’s usually edited and sweetened,” he says, referencing the canned laughs added to most stand-up specials. “This is live, and soured.”

Because comedy is so “subjective,” Ross says it’s not always easy for him and his fellow judges to pick a winner. “It’s how hard you laugh at the end of the day,” he says. “We do take into account originality and performance, but I want the judges to have fun.”

When comedian Whitney Cummings judged one of the earlier rounds this time, she almost had to take a break because of how brutal the jokes were. “My only requirement of the judges is that they care,” Ross says. “The comedians are working so hard, I just want the judges to take it seriously.”

Sometimes, the judges even end up getting roasted by the contestants. For instance, in this exclusive clip from Saturday night’s show, comedian Matthew Broussard tells musician John Mayer that the jokes he would tell between songs at his concerts inspired him to go into stand-up. “That’s when I realized you could be funny while staying true to yourself as a cocky, pretentious douchebag,” he says to cheers from the crowd. It only gets more brutal from there.

As mean as Ross can be when he’s in roast mode, he displays none of the Simon Cowell-style cruelty that has become a staple of other reality competition shows. And because he’s friends with many of the comics who compete, Ross struggles with each tie-breaking decision he has to make as the third judge to weigh in on a given round.

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“I wish I could be more critical, but sometimes my heart just tells me this comedian needs some positive reinforcement,” he says, sweetly. At the after parties, he always goes over and says hello to the losers first to make sure everything is cool between them.

“I always had a feeling that there was a lot of potential here,” Ross says of the show, which was a surprise hit for Comedy Central last summer. “I feel like this is what we as a country need right now.” Echoing comments made by guest judge Sarah Silverman at Saturday’s quarterfinals, Ross says he views Roast Battle as a chance for people to “troll” each other in real life instead of on Twitter.

Or, as President Obama said in his farewell speech this month, “If you’re tired of arguing with strangers on the internet, try talking with one of them in real life.”

“I hate bullies,” Ross adds of trolls who “pick on somebody who doesn’t volunteer.” That’s why he loves roasting so much. “It’s done voluntarily, with affection.” (Among the rules of Roast Battle is that the roasters have to hug at the end of each round.) “It’s so important to laugh at ourselves, and our differences,” Ross says. “It’s really bringing people together.”

Before any pair of comedians set out to battle, they actually provide each other with ammunition in the form of personal information that can range anywhere from “I was a nerd in high school” to “My brother just died a few months ago.”

Ross encourages them to meet in person ahead of time and talk things through. “If there’s something that’s off-limits or you don’t want mentioned,” that’s the time to let it be known, he says. “Some comedians might want to win so badly that they bring it up anyway, but that doesn’t happen often.

“It’s a brutal show, it’s brutally honest. So yeah, if you step into that arena you might have to hear about your dead parents,” he adds. “I don’t know if I could handle it.” That being said, Ross says he does get “jealous” of the roasters from time to time—“I get a little bit of ball-busting blue balls”—and suggests that he could make himself a contestant at some point. He just hasn’t “found the right opponent yet.”

One idea he has is to invite Katie Rich, the suspended SNL writer, to compete on Roast Battle III. “She sounds funny and if she wants to battle I’d love to see what she’s got,” Ross says. “I think she’s probably got the right attitude for us.”

The show is no stranger to “controversial” battlers, including Kurt Metzger, who infamously defended another comedian who had been accused of rape and was knocked out of the competition on Thursday night’s premiere. Last season, the show gave a platform to The League’s Steve Rannazzisi, who attempted to redeem himself after he was outed for lying about escaping the World Trade Center on 9/11. Ross made him go up against a New York comic.

“I’m a big believer in second chances,” Ross says, adding that the celebrity roasts he’s hosted have served a similar purpose over the years. “It was great for [Justin] Bieber after he got in all kinds of high-profile situations. It was great for Charlie Sheen. Roasting definitely is a healer.”

It was a mere six years ago that Donald Trump was the target of Ross and other comedians at his own Comedy Central roast. Ross ran into the new president in Palm Beach, Florida, just a few weeks before he was inaugurated. “He definitely is a big comedy fan,” he says of the conversation they had about Trump’s favorite comedians, including the late Joan Rivers.

“It did occur to me when I was watching the debates, that they were very much like a roast battle,” Ross says. They also reminded him of the rap battle scenes from the Broadway musical Hamilton, the way “our forefathers” used “humor and insults” to get their points of view across. “And it really works,” he continues. “Humor is a weapon, and used correctly it can really neutralize somebody. President Trump did that. He really used his roasting skills to pop in those debates.”

“He talked to his opponent, whereas Secretary Clinton talked about her opponent,” Ross explains. “When you turn to somebody and say, ‘You should be in jail,’ it’s a roast. She would turn away and say, ‘My opponent thinks…’ as if he wasn’t there, when in fact she could have turned right at him and said, ‘Your barber should have been in jail.’ Boom!”

Clinton could have used the Roastmaster General in her debate prep sessions. “Believe me, I tried,” Ross jokes.