Roasting can be a dangerous profession — not everyone can take a joke — and Ross has experienced all the highs and lows it has to offer. “These roasts, there’s good ones and there’s better ones, but they’re like Super Bowl games. People kind of remember them forever,” he says. Here are a few of his many memorable moments from the dais:
Saving Rob Schneider
Just a few weeks after 9/11, Ross insisted the show go on and turned a roast of Playboy entrepreneur Hugh Hefner into a charity event. Comedian Rob Schneider was near the beginning of the lineup, and Ross began to worry when Schneider began to flail. “Is this going to be a sad show?” says Ross. “Is this going to be depressing? He had one more clunker, and I ran up there and I put my arm around him, and I said, ‘Rob, hasn’t there been enough bombing in this city?’ And he laughed, and Hef cracked up, and the place just sort of opened up. I felt a cloud lift from the room. For whatever reason, Rob started killing after that. I sat back down, Rob just got into his groove and relaxed and we kind of got that energy lifted. I felt very proud of that moment.”
Flipped off by the Queen of Soul
Ross was amazed to find that Aretha Franklin was opening up a Friars Club roast of Matt Lauer by singing “God Bless America.” While the Queen of Soul was singing, he wrote a joke in the margin. “I go up there and I go, ‘Wow, what a show! I’ve never been to a show where the fat lady sings in the beginning,’ ” he says. “She gave me the finger. But she was laughing while she gave me the finger, and I ran over and gave her a big hug. It was a great moment. She had a great sense of humor. Let it be known that the Queen of Soul has thick skin.”
Billionaires don’t like surprises
“I never roast people who don’t ask for it,” says Ross. “One time at a private affair in Toronto, [Virgin Group founder] Richard Branson’s friends hired me to perform at a private party and roast him. When you’ve got a powerful guy caught off guard, that can be very dangerous.” He seemed to be taking it well, though, even as Ross went through three pages of killer material. “I asked him at the end if he wanted the have a rebuttal or say anything back. And he got up and he gave me a hug, and he poured his drink on the top of my head. So there was me learning my lesson to only roast people who are volunteers. I had to say goodnight and walk off and collect my paycheck while I was soaking wet with gin.”
Nick A. Zaino III can be reached at email@example.com.