Comedy roast pro Jeff Ross appears Sunday at Clusterfest. (Courtesy photo)

Slinging insults a lifelong pursuit for Jeff Ross

Before comedian Jeff Ross performs in a city, he conducts careful research, looking up the news, topics and trends for each area, in an effort to make sure his gig is topical and timely.

Then he burns the script and hopes all hell breaks loose.

Ross, who has earned the sobriquet of the RoastMaster General for his brutally hilarious takedowns of celebrities, is truly in his element when he’s exchanging impromptu verbal volleys with the audience, ditching notes in favor of no-holds barred humor.

“I prepare for my shows way ahead of time, but once I get onstage, it’s more like planned chaos,” says Ross, who appears Sunday during the second Clusterfest comedy and music festival in San Francisco’s Civic Center Plaza. “I don’t really know what’s going to happen at times — who I am going to talk to, who I am going to bring up. That’s the beauty of being a comedian; it’s not a science.”

Ross, an old-school comedian, has a thick skin and preternatural ability to fire off insults at will. He plied his trade as youngster growing up in New Jersey, where, he says, many people were self-proclaimed comedians who lived to “bust the chops” of their buddies. He further perfected his ability to fire zingers while working for his father’s catering company, an ethnically diverse outfit where people loved to give the boss’ kid a hard time.

That background made him a natural fit to be a comedian, though he says his career has been the result of a “happy accident.” On a whim, his friend suggested he try standup, and after his first gig, he was hooked.

“That first time was an absolutely euphoric experience,” says Ross. “And then maybe the next 30 times were completely terrible. But I kept at it. I knew I was in it for the long haul.”

He’s made a niche for himself by being an integral part of the Comedy Central roasts on TV, ostensible tribute sessions that turn into vulgar and uproarious mudslinging contests. His set on Sunday is billed as “Jeff Ross Roasts Clusterfest.”

“In a way, roasts are almost therapeutic and normalizing, because you know what’s coming is going to be brutal and you just have to take it,” he says. “Roasting is truly an equal opportunity offensive act.”

Although roasting is his specialty, Ross has an affinity for comedy festivals, and he asked to take part in this year’s Clusterfest after sitting out the inaugural edition in 2017. After lengthy trips alone on the road for standup gigs, being surrounded by a bunch of like-minded comedians is a nice reprieve.

“You’ve got everyone here from Jon Stewart to Wu Tang,” says Ross. “If you can’t have fun at this thing, you might as well give up.”

Where: Bill Graham Civic Auditorium and Civic Center Plaza, 99 Grove St., S.F.
When: 5 to 11 p.m. June 1, 2:15 to 11 p.m. June 2, 2:15 to 10:15 p.m. June 3
Tickets: $135 to $289.50

June 1: Trevor Noah at 8:30 p.m.; The Lonely Island at 10 p.m.
June 2: Amy Schumer and Friends at 9:15 p.m
June 3: Jeff Ross at 8:15 p.m.; Jon Stewart at 9:15 p.m.

With Comedy Central “rising stars” in the Bill Graham Civic
Standup: Chris Redd, Tim Dillon, Robby Hoffman, Mekki Leeper, Amy Miller, Lucas O’Neil, Dewayne Perkins, Pat Regan, Chris Tellez (7:15 p.m. June 1)
Standup: Jullian McCollough, Mark Normand, Molly Austin, Garrick Bernard, Nick Nemeroff, Steph Tolev, Sydnee Washington, Daniel Webb, Jaboukie Young-White (5 p.m. June 2)
Variety: Matthew Broussard, Patti Harrison, Rachel Pegram, Lorelei Ramirez, Peter Smith, Sam Taggart, Mark Vigeant, Bowen Yang (6:30 p.m. June 3)

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