A week into his first major stand-up tour in eight years, Dave Chappelle had one of the worst nights of his career. It was at the Hartford, Connecticut, stop on Funny or Die’s Oddball Comedy and Curiosity Festival, a 15-date amphitheater run Chappelle is headlining. The crowd of 8,000 was rowdy – exactly how rowdy is up for debate, though they reportedly pelted him with shouts of “You suck!” and “I’m Rick James, bitch!” Chappelle would later call the audience “young, white alcoholics” and “suburban torturers.”
At some point, Chappelle seemed to give up trying to tell jokes, choosing instead to sit on a stool, smoke American Spirits and chat idly with the audience until his contractually obligated 25 minutes were up. “I like some of you. I hate some of you,” he said. “I forgive some of you, but I don’t forgive all of you.” Then he walked off the stage as the DJ spun Kanye West’s “New Slaves.”
Chappelle was already one of the most notorious quitters in the history of show business. A decade ago, Chappelle’s Show established him as maybe the funniest man on the planet, thanks to hilarious sketches with broad appeal – featuring everything from a black KKK leader to a white family called the Niggars to Chappelle’s bonkers impressions of Lil Jon, Prince and, yes, Rick James.
But in 2005, Chappelle walked out during production of the third season, leaving $50 million on the table and sparking rumors of drug abuse and mental illness. Burned out by fame and feeling like the show’s racially charged humor was becoming socially irresponsible, Chappelle bolted to Africa without telling anyone except his brother, then settled into life as a family man on his Ohio farm. He’s laid low since, playing sporadic stand-up gigs, until a run of club shows earlier this year.
This history made the Hartford incident big news. Some in the crowd blamed Chappelle for not powering through the hecklers, and Hartford’s mayor accused him of “whining.” One writer, present at the show, even speculated he had just quit stand-up forever. But he also got plenty of support – from the rapper Talib Kweli, who flew out to join his buddy on tour, and from comics like Jeff Ross, who’s MC’ing the Oddball Fest. “It wasn’t a meltdown – it was a show cut short by a shitty audience,” Ross says.
“I wanted to throw up,” adds Live Nation Comedy president Geof Wills, a longtime friend of Chappelle’s, who organized the Oddball Tour and was at the show. “I would have understood if he decided not to continue with the tour. But within a very reasonable amount of time, Dave told me, ‘I’m going to keep going.'”
Not only did Chappelle keep going, he spun the incident into huge laughs. “You know how bad it feels to get heckled by a room full of motherfuckers with crocodiles on their sweaters?” he said three nights later in Detroit, hopping right on the elephant in the amphitheater. He compared his Hartford debacle to Michael Richards’ n-word-studded onstage meltdown in 2006 (“At least I didn’t have to meet with Jesse Jackson after my show”), then expressed kinship with, of all people, Paula Deen: “I did feel bad for her – as a matter of fact, I hired her as my personal chef.”
The rest of his 45-minute Detroit set killed, suggesting that his stand-up gifts have only deepened. He just turned 40 (he celebrated during a tour stop in Houston, with a party DJ’d by his friend Erykah Badu); though he’s added muscle to his pipe-cleaner physique, he still makes use of an actor’s arsenal of eye rolls, voice inflections, dramatic pauses and great impressions of square white dudes.
What’s different is the way he turns his personal life and professional dramas into brilliant comedy, often in meandering stories with a touch of melancholy. “He’s more reflective,” says Oddball tourmate Hannibal Buress. “He’s talking about leaving the show, about his relationship with his wife, different things he wished he could have talked about.” Ross agrees. “I’ve been blown away by his new material,” he says. “I never saw him open up about his family and his career in that way.”
In one of the best bits in Detroit, he recalled a friend assuring him that, despite losing $50 million, he still had his integrity. Chappelle snaps back with a hint of bitterness: “That’s great! I’ll go home and feed the kids some integrity sandwiches.” At another point, praising and mocking at once, he told the crowd, “You don’t look bankrupt to me! As a matter of fact . . . you have helped pull me out of financial ruin.”
Even as Chappelle performs for huge crowds each night, he remains his own kind of celebrity, refusing all TV appearances and interviews. And he’s clearly in no hurry to get back to Chappelle’s Show-level fame. “He’s a stand-up through and through,” Wills says. “All the other stuff is secondary.”
The Oddball Fest runs through September 22nd. After that, according to one rumor, Chappelle may tour with Chris Rock. He could just as easily disappear again. Unpredictability is part of what makes him fascinating, and he knows it. “All those people in Hartford felt lucky: ‘We got to see Dave Chappelle freak out!'” he said in Detroit. “It’s like Siegfried and Roy. You don’t go to see somebody be safe. You go thinking, ‘This motherfucker might get bit.'”
This story is from the September 26th, 2013 issue of Rolling Stone.