Aspen Laugh Fest: Jeff Ross on roasting the world to save it

Few would have predicted that Jeff Ross, the “Roastmaster General” who spent years lambasting celebrities onstage and who made an immortal joke about what he wouldn’t do with Bea Arthur’s penis, would become arguably the most socially relevant comedian of our time. Nobody would have guessed he’d be the guy to unite, if only briefly, a bitterly divided country.

But here we are. Using the roast format as an unlikely common ground, Ross has brought together cops and protesters, immigrants and border hawks, the imprisoned and the free.

Ross, who headlines the Aspen Laugh Festival today, took his act to the literal border in Brownsville, Texas, for “Jeff Ross Roasts the Border” last year. Premiering in November on Comedy Central, the groundbreaking mix of stand-up special, roast and documentary featured ICE agents and coyotes and border-hoppers. It followed the similarly minded 2016 special “Jeff Ross Roasts Cops,” which inserted Ross into the Black Lives Matter movement, and 2015’s “Jeff Ross Roasts Criminals,” filmed in a Texas jail where he humanized convicts and tackled mass incarceration.

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Armed with his thick skin, quick wits and the barbed insult comedy he’s honed for decades, Ross has hopped into the crossfire of the country’s most contentious issues and found more than laughs (though he gets plenty of those). He’s found that rarest of things in the Trump era: a forum for people who disagree to listen to one another.

“There’s nothing worse than a preachy comedian with no punchlines. All these ‘woke’ comedians are putting me to sleep.”Jeff Ross

“If one group is looking left and the other is looking right,” Ross said in a recent phone interview from Los Angeles, “how do I get them to turn around and face each other?”

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In his regular stand-up act, Ross has long done “speed roasts” of audience members who volunteer to take the stage and have Ross make fun of them. Burning a diverse lot of audiences, he explained, made him realize the potential for the format to do more than embarrass celebrities on television. He’d speed-roast a war vet or a disabled person or an immigrant. He’d get laughs from the crowd, then he might get a hug or an emotional thanks from the roastee.

“I’d start to get their story and normalize them, in a weird way, to the rest of the audience,” he said. “I’d do that and I’d go, ‘Wow, comedy really does bring people together.’ People are laughing at themselves and their insecurities. It felt like some good was happening that I couldn’t always articulate.”

Something happened with these ordinary folks that didn’t happen with Charlie Sheen or Pamela Anderson or Trump during their roasts on Comedy Central.

“I just saw how happy it made people,” Ross said. “So I saw there was something happening here.”

From there, it wasn’t a huge leap to begin using the roast format on thorny social issues. He’d waded into this territory a bit back in 2005 in his documentary “Patriot Act,” about his shows for troops in Iraq. So he knew what to do when the battles raging on the home front came calling.

“I was watching the Black Lives Matter rallies and the cops’ reaction and I had to think about how I felt about cops as a kid and what the discrepancies were,” he said of the cop roast. “It was like a call to action.”

For the border special, he saw Trump’s “build the wall” campaign and the heated rhetoric about immigrants and refugees taking hold. It made Ross think about growing up in New Jersey, surrounded by immigrants from Europe and Asia: “I thought, why are these people getting such a bad rap all of a sudden?”

He’s spent about a year researching the most recent roast projects. He’s unsure what he’ll tackle next, with so many divisive issues to choose from.

“I feel like I need to break it up. I could do half-hours on lots of them,” Ross said.

When doing comedy and social commentary, however, Ross is careful not to lose sight of the laughs. He’s dismissive of the emergence of self-serious comedian philosophers.

“There’s nothing worse than a preachy comedian with no punchlines,” he said. “All these ‘woke’ comedians are putting me to sleep.”

Being a road comedian in this tumultuous moment can be treacherous and intimidating. Many comics are scared of crowds turning on them and thus avoid the kind of divisive issues that Ross has tackled. Comedian Whitney Cummings, when she was at Laugh Fest last year, told a story about a fight breaking out in the audience when she first tried talking about Trump in her act in 2016.

Ross, a devoted student of the history of comedy who grew close to elders like Don Rickles, said he doesn’t know if there’s a precedent for this kind of overheated environment for comedy.

“I used to go to Buddy Hackett and Milton Berle with these questions and they’re not around anymore,” he said. “Now younger guys and (journalists) ask me. And there’s no guidebook.”

Whatever a comic’s beliefs may be, Ross reasoned, it’s their job to make both sides of any disagreement laugh.

“I don’t only want to make people who agree with me laugh,” Ross said. “I don’t want to pontificate to people who don’t agree with me. The real win for me is when I can get people who disagree with one another to laugh at the same thing. That’s when people start to find humanity in one another and they look at each other in a different way.”

Ross comes to Aspen fresh off of a few weeks in Europe supporting Chris Rock on his “Total Blackout” tour, playing to huge crowds in arenas.

“I’m gonna miss that life,” he said. “The adjustment of taking my act up to arena level was really fun. It was like being a rock star. But I missed the intimacy of clubs and theaters, too.”

Along with the speed-roast portions of the show, Ross’ new act — with no leftover material from his last special — touches on the #MeToo movement and some politics. But it is also, Ross said, more personal than a lot of what we’ve heard from him over the years: “This is the most vulnerable act I’ve done — talking about myself a little bit.”

This weekend marks his first time in Aspen since the old days of HBO’s U.S. Comedy Arts Festival.

“I was delighted when I heard I got to go back,” he said. “I remember hearing about Aspen and always thought, ‘This is going to be some giant skiing oasis.’ And then you get there and you see the same people everywhere you go and it’s this cozy, quaint place with lots of fireplaces. And that odd mix of drinking and skiing, which sounds dangerous.”

Ross said he hasn’t skied since he was a teenager, but might give the bunny hill a whirl while he’s in town. Or, he suggested, he might partake in Colorado’s other favorite recreational activity: “If there’s marijuana everywhere, who knows? I might just take a puff and walk around the mountains and do a little ski slope in my head. It sounds safer.”

atravers@aspentimes.com