In 2011, stand-up comedian Jeff Ross and others roasted Donald Trump on Comedy Central. Ross had no idea that Trump would go on to win the Republican nomination, but in hindsight, Ross isn’t all that surprised that he did.
“As a New Yorker, I never rule him out of anything,” Ross said on CBS Sports Radio’s The Doug Gottlieb Show. “He owns New York, so it’s not surprising that he could take over the rest of the country. I won’t be surprised if he goes after Poland and Czechoslovakia next.”
Doug Gottlieb actually thought Ross, who never holds back, went a little easy on Trump that night.
“Well,” Ross said, “I don’t want to die of a drone strike one day, okay?”
If you like the Roast series – and you should – you’re in luck. This week, Comedy Central is airing a four-part Roast Battle from July 28-31. It will feature Ross, Judd Apatow, Whoopi Goldberg, Kevin Hart, Seth Rogan and others.
“We’re the judges,” Ross explained, “and 16 comedians – it’s a bracket, a tournament, kind of like a March Madness for roasting – and it airs all week on Comedy Central. The judges are expert comedians, sort of like people with some roasting experience. Sarah Silverman and Judd Apatow are judging the final. Kevin Hart and David Spade are on (Thursday). Anybody in the room (can be roasted). It’s sort of like a Fight Club scenario. It’s two newer comedians roasting each other. They work weeks on it, kind of like going to battle, and they roast each other back and forth, tit for tat, four jokes each, and then the judges weigh in and I have final say. It’s a crazy show. You kind of have to see it to believe it. It’s a temple of free speech. It’s way more intense and mean than the celebrity roasts.”
The celebrity roasts, of course, are a lot of fun, and – somewhat stunningly – no one has ever gotten mad at Ross for them. Not as far as he knows, anyway.
Some viewers thought Flavor Flav was angry during his roast, but that wasn’t the case.
“Nobody’s ever been more delighted by all the attention than Flavor Flav,” Ross said. “He was sort of like kicking his feet in the air like a little kid. I think people, even if they look a little mad during the roast, by the time they get their rebuttal or they go home and watch it, I think that they kind of get what happens. It’s kind of like a party. I want everyone to leave the roast thinking that was a really good time.”
Ross said of all the roasts, he’s most proud of the Justin Bieber one “because we saved his life.”
“I think it was a good wake-up call,” Ross said. “It was kind of like life rehab for him. He straightened out, and now look at him. He’s got the No. 1 album in the world and No. 1 tour.”
As for the roast Ross hasn’t done but wants to do the most? Kanye West, following by Bill Clinton.
“I feel like Kanye would be the greatest roast ever,” Ross said. “It could be a three-part mini series.”