SAN FRANCISCO—Jeff Ross arrives to our interview armed with nunchucks. If he’s trying to intimidate me, it’s working.
The “Roastmaster General,” as he has come to be known in the comedy world, has just arrived in this city from Los Angeles. He’s wearing a bright blue kimono jacket and a red fedora and seems genuinely thrilled to be on the scene at Comedy Central’s second annual Clusterfest weekend.
“There were so many comics on my plane, we had to go through an insecurity check point,” he jokes before asking, “Was that good?” Despite the weapon now slung over his shoulders, he’s just as emotionally needy as any other working comedian and is always hoping for a laugh. I oblige.
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Ross is here to open for his “favorite comedian,” Jon Stewart, who’s headlining the last night of the three-day festival. But instead of doing stand-up, Ross will be roasting brave members of the audience who, for some reason, want to be subjected to his brutal jokes about their race, age, body or general Bay Area hipster disposition.
“Any time people are at a festival, they’re eager to get roasted and you can say things that are even more crazy than at a regular show,” Ross tells me as we walk out onto a balcony overlooking the massive crowd below that’s taking in an afternoon performance by comedian and musician Reggie Watts. “You can cut a little deeper, because they’re warmed up.”
This year’s festival is happening hot on the heels of a series of comedy-based scandals: Michelle Wolf coming under fire for her jokes about Sarah Huckabee Sanders, Roseanne Barr getting her show cancelled because of a blantantly racist tweet, Samantha Bee supposedly “crossing the line” on hers. Do incidents like those make Ross worry that he might inadvertently say the “wrong thing” and get in some “trouble” of his own?
“When I see that Comedy Central is behind this, I know that I’m protected,” he says. “They always stick up for comics. And I feel like it’s part of our responsibility not to hold back. If other people aren’t censoring us and we start censoring ourselves, then I don’t think I’d want to be a comedian. The only reason I love being a comic is that I get to say what I want.”
Since he was a kid growing up in Springfield, New Jersey, Ross says he was always proud to live in a country where you could “make fun of anything,” including the president of the United States. And despite Donald Trump’s seeming refusal to laugh at himself in public, Ross knows a different side of the president. “When I tell a joke about Donald Trump, most of the jokes he would laugh at,” he says from experience.
“I’ve roasted you twice for charity and you’ve always been a good sport and even called me afterwards to tell me how much fun you had,” he wrote in a recent article for The Daily Beast, urging Trump to reconsider his decision to skip the annual White House Correspondents’ Dinner.
If Ross could speak directly to the president, he says he would tell him it would be beneficial for him to show his constituents that he can “take a joke,” because a roast is “not a court of law, it’s not a debate. It’s a party. And it’s a great exercise of free speech.”
The night before, Ross was performing at a benefit for Chrysalis, an L.A.-based non-profit organization that helps people in poverty get jobs. He did a lot of jokes about Trump during his set and afterwards someone came up to him to tell him how “brave” he was to tell jokes that the president would “hate.”
“I said, ‘No he wouldn’t, he would love them, he would be repeating them to his friends,” he says. “In public, he would pretend to be offended and not think they’re funny, but that’s part of his schtick.”
In Ross’ telling, it was a joke about Hillary Clinton that got the biggest laugh of the night from the liberal L.A. audience. “You know, on Election Night I was in New York and I got invited to Hillary Clinton’s victory party. And I went,’” he told them, before asking, “Have you ever gone to a wedding and the bride dies walking down the aisle?’”
Ross is no stranger to controversy himself, having dressed up as figures like Muammar Gaddafi and Joe Paterno for past Comedy Central roasts. In 2012, at the Roast of Roseanne Barr, he told a series of jokes about the recent mass shooting at a movie theater in Aurora, Colorado.
“Congratulations. This is actually a great night for you,” Ross told fellow roaster Seth Green, who, like the shooter in that incident, has red hair. “You haven’t gotten this much attention since you shot all those people in Aurora.” He then added, “I’m kidding. You are not like James Holmes. At least he did something in a movie theater that people remember!”
Ross refused to apologize for that joke—“We should be more focused on guns that kill than jokes that sting,” he said at the time—and hasn’t offered any public apologies for any other jokes since.
“I’ve never apologized for a joke,” he tells me. “But I have apologized for hurting someone’s feelings.” Ross says he “feels sorry” for the comics who get “bullied” into making “sincere” apologies for jokes. “It doesn’t sit well with me,” he says. “Bad taste is not a crime.”
He also doesn’t like the phrase “push the envelope” because he believes comics “define the envelope, we make the rules.” In his view, “everything’s OK to make fun of” and “nothing’s off limits.”
“I find it troubling,” Ross says of this recent backlash to comedy. “And I just hope that one of your readers can text me or email me a list of acceptable topics to make fun of, because the list keeps getting updated. It really drives me nuts.”
A couple of days earlier, Ross tweeted a similar question that now sits pinned to the top of his Twitter profile.
Despite the bad rap that colleges and universities have gotten for being “P.C. safe spaces” that are not welcoming to comedians, Ross says he still loves performing for—and roasting—students.
“My show hits pretty hard,” he says, “but my show’s interactive and college students love that.” He will bring students up on stage and make fun of them to their faces and they “always take the jokes pretty well,” he adds. “So I never sign on to that belief that college kids are overly sensitive. I think generally the world is more sensitive and college kids are no more or less sensitive than anyone else.”
At a panel discussion with a handful of comedians the day before our conversation, stand-up comic and SiriusXM radio host Nikki Glaser said she is anxious to see what the next Comedy Central roast will be like in this time of heightened sensitivity. “If you compare what Michelle Wolf did to the things that are said on the roasts, it’s insane how mean the roasts get,” she said.
This summer, Ross is set to lead the latest Comedy Central roast of Bruce Willis. When Ross was walking around the festival grounds earlier in the day, he got a call on his cell phone from Willis, who was checking in about the upcoming event. He told Ross, “I just want you to know, and tell everyone else, not to hold back. I want you guys to throw rocks, because I’m going to throw them right back.”
“I was so moved by that,” Ross says. “Because most people go into these roasts nervous. We live in such a touchy society right now and here’s a guy going, ‘Bring it.’”
Legend has it that comics at the roast of Donald Trump—an event that occurred just five years before he was elected president—were not allowed to joke about the real estate mogul’s net worth, something that Glaser suggested led Wolf to make her “How broke is he?” riff such a big part of her White House Correspondents’ Dinner speech.
Before Wolf did her bit about Trump being “broke” at the dinner in April, she reached out to Ross to ask if it was true that the president is “sensitive” about that topic. “Absolutely,” he told her.
However, Ross clarifies that is “actually not true” that comics were not allowed to joke about Trump’s financial status. “My understanding is that nothing was off-limits,” he says, noting that he made a joke on that topic from the dais: “I said his book The Art of the Deal has three chapter elevens.”
It wasn’t that jokes about Trump’s fortune—or lack thereof—were not allowed, it’s just that Trump didn’t find them funny, “which makes them funnier,” Ross says.
