Before roasting NFL Hall of Famer Emmitt Smith in 2003, comedian Jeff Ross knew he was going to have a few zingers for one of the bigger guests, basketball star Shaquille O’Neal.
But since Shaq had invited him to the event — and stood at an intimidating 7-foot-1 — Ross figured he ought to warn him beforehand.
“Are you going to be able to take these jokes?” Ross asked.
“No one ever asked me to hold back on the basketball court,” O’Neal responded. “I’m not going to ask you to hold back on the roast dais.”
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During the roast, Ross’ best Shaq joke — “Your knuckles are scraped — did you walk here?” — drew roars from the crowd and had Shaq reeling back with laughter.
“Afterward, we all went out and played craps, and I won a thousand bucks,” Ross said. “I just said, ‘Lemme bet whatever Shaq bets.’ ”
Ross, who will bring his comedy act to San Luis Obispo on Saturday, is known for his biting roasts of celebrities, with targets that have included Pamela Anderson, Joan Rivers, Flavor Flav, Charlie Sheen, Hugh Hefner and Donald Trump. But a good roastee, he said, has to have a thick skin.
“Obviously, they have to be able to take a joke,” he said. “They have to be a good sport.”
If Ross was born to be an insult comic, it took him years to figure it out.
After losing both parents while in his teens, the New Jersey native studied communications at Boston University, where he worked as a DJ and played in a punk band called High Gear Daddys.
“About two years after college, I was going through a really hard time — had no direction, didn’t have a lot of friends,” he said. “I was living in New Jersey with my grandfather. I was just sort of a chubby loser. And my pal Mark Chapin said, ‘You should take this class at night just for fun — it’s taught by a comedian.’ And I did.”
As stand-up was booming, Ross began performing observational humor. While he had success as a comedian, he was not widely known until he shifted his act — motivated by a gig with old-time comedy legends. In 1995, he was invited to participate in a Friars Club roast of actor Steven Seagal. Although the famous roasts had taken place for decades, their popularity had waned.
“It was kind of an off year,” said Ross, who’d never participated in a roast before. “They couldn’t really get anybody who cared enough about Steven Seagal.”
Even Ross focused most of his jokes on some of the other roasters.
“When I saw Buddy Hackett, Milton Berle and Henny Youngman, I said that is truly Mount Roastmore right there,” said Ross, who became friends with Berle. “And I kind of ignored Seagal and went for these other guys.”
Becoming ‘Roastmaster General’
After a successful roast performance, Ross’ career began to focus on insult comedy and roasts in the tradition of Don Rickles and Rodney Dangerfield.
Eventually he would become “Roastmaster General” of the popular Comedy Central Roasts.
The roasts feature celebrity guests, who are razzed by other celebrities. But everyone on stage gets zinged at some point, including Ross.
“I must admit, sometimes the jokes can sting,” Ross said. “But I can deflect them with crazy outfits and hairdos. If they make fun of my hair or my outfit, it deflects them from making fun of my career.”
Ross said he doesn’t necessarily have a favorite roast.
“The preparation is what I love,” Ross said. “Writing the jokes with my friends, trying them out, getting a haircut, finding a funny costume to wear. The process is so exhilarating, my favorite roast is the one I haven’t done yet.”
The most famous roast was for Pamela Anderson, though the most searing jokes were targeted toward panel member Courtney Love, who appeared to be under the influence.
“That was really a game changer,” Ross said. “That was the most punk rock roast I’ve ever done. It was so over-the-top. Jimmy Kimmel literally had to hold Courtney Love down.”
Ross’ biggest joke was, “How is it possible that Courtney Love looks worse than Kurt Cobain?” a reference to Love’s partner, who committed suicide with a shotgun.
“Having Courtney Love there was really an oil spill,” he said. “It was just so much fun. We could have a weekly Courtney Love Roast.”
While some of the roast jokes come off harsh, Ross said comics try to make light of bad situations.
“Comics have a responsibility to shine a light on the darkest place in our society,” he said, something he said the late Joan Rivers did well.
Rivers, he said, was one of the best roastees.
“In the wake of losing Joan Rivers, it made me realize how amazing her rebuttal was at the end of her roast,” he said. “She went up and just skewered everybody.”
This past weekend, Ross reached another career milestone — roasting Krusty the Clown in an episode of “The Simpsons.”
“That show, I’ve been watching it, I think, since I was in college,” he said. “And to be on the season premiere and also be teamed up with my comedy sister Sarah (Silverman) makes me so happy.”
Ross, whose show “The Burn with Jeff Ross” airs on Comedy Central, will offer observational humor, social commentary and maybe even a few love poems during his Fremont show. But the “Roastmaster General” will also invite audience members to the stage for a speed roast, during which Ross will insult them.
“People love to be the center of attention, even when there’s a target on their shirt,” he said.
Because he’s known for his roasts, people who meet Ross in public often try to roast him.
“Everywhere I go,” he said. “Just because I’m the roast guy, they will go into roast mode in the middle of an airport or the Taco Bell drive-through. So I have to absorb these insults. But I’ve become a better man for it.”
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