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Dave Chappelle’s Rise From Rick James to Radio City: A Timeline

As the comic starts his NYC residency, we chart his career from the early days to post-‘Chappelle Show’ pop-up appearances

Dave Chappelle

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"Technically, I never quit," Dave Chappelle recently told David Letterman. "I'm seven years late for work." Actually, it's more like nine years since he walked away from Chappelle's Show in May, 2005. But now is not the time to argue over details, since America's most-missed comedian is returning for nine consecutive shows at Radio City Music Hall, June 18 to June 26.

Dave Chappelle Talks Kanye, Prince on 'The Tonight Show'

Chappelle, who infamously walked away from a contract that might have been worth as much as $100 million, has been making low-key appearances in stand-up clubs around the country for a few years, but this is the high-profile comeback his fans have been craving — complete with musical guests, including Erykah Badu and Nas. On the eve of his return, we retrace the winding path that led from Fairfax, Virginia and Yellow Springs, Ohio, through New York and South Africa, back to Manhattan's Radio City Music Hall. By Logan Hill

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1991

Chappelle moves to New York City and is immediately booed off the stage during the Apollo Theater's famous "Amateur Night" showcase. "That night was liberating," he would later tell Inside the Actors' Studio host James Lipton, "because I failed so far beyond my wildest nightmares of failing, that it was like, Hey, they're all booing. My friends are here watching, my mom, and this is not that bad. After that, I was fearless." He learns to work crowds at comedy clubs at night, and plays to strangers in Washington Square Park on weekends. He signs his first TV development deal at age 19. 

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1992-1995

Chappelle blows up on the New York comedy scene. In 1992, he appears on AMC's Caroline's Comedy Hour and HBO's Def Comedy Jam. Then Mel Brooks casts him as "Ahchoo" in Robin Hood: Men in Tights. But he turns down the part of Benjamin Buford "Bubba" Blue in Forrest Gump, because he feels it's too insulting (and later mocks the film in a 1997 skit). He auditions for Saturday Night Live and is rejected. But he lands a part opposite his role model Eddie Murphy in The Nutty Professor, which is released in 1996.

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1996

ABC, which had promoted Chappelle with a Home Improvement cameo the year before, premieres Dave Chappelle's sitcom Buddies, a severely compromised version of the sitcom that Chappelle had been developing. Nobody likes it, not even Entertainment Weekly, which writes, "The worst thing about the show is that it makes racism boring." Despite Chappelle's compromises and the addition of white characters, the show is abandoned. "He lost his innocence on that show," his agent Barry later said in Searching for Chappelle. Soon after, Fox after executives pressure him to recast a role in yet another series to broaden its appeal. Chappelle leaves the project; the ensuing controversy is covered in a Variety article headlined "TV's Race Card."

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1998

Despite earning just $17 million in theaters, Dave Chappelle's Half Baked (co-written by Neal Brennan, who will later collaborate on The Chappelle Show) makes him a hero to potheads. He also earns him enough money to buy sixty-five acres of land near his childhood home in Yellow Springs, Ohio, which will become his home away from Hollywood. That same year, Chappelle converts to Islam, though he rarely talks about his religion in public. He premieres his first HBO comedy show, HBO Comedy Half-Hour: Dave Chappelle. And he continues to develop TV projects that never make it on-air. The final count? Eleven failed pilots.

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2000

Chappelle films his first hour-long stand-up special, Dave Chappelle: Killin' Them Softly in Washington, D.C. He tackles controversial subjects, like drug-dealing babies and the culture of poverty arguments instilled in young children on Sesame Street. For instance: Oscar, Chappelle argues, is perceived to be grouchy, when, really, he's just poor: "Bitch! I live in a fuckin' trashcan!"

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January 22, 2003

"The idea was to do a variety show that was personal," Chappelle tells Howard Stern about Chappelle's Show, which premieres on January 22, 2003. "It was like taking somebody on a tour through a young black man's subconscious, and I don't think America has been there," he would later tell Esquire. "So in a way it was kind of like reality TV, right?" In one of the show's first break-out hits, Chappelle plays Clayton Bigsby, a blind racist Klan leader who doesn't know he's black. The comedy masterstroke is so powerful it knocks Charlie Sheen off TV. "I laughed myself into a hernia," Sheen would later say, claiming that the real reason he missed tapings of Two and a Half Men and got fired was not drugs or prostitutes or ego but Chappelle's Bigsby sketch. "That is 100 percent true. It's his fault. There you go. Dave Chappelle cost me my job."

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February 26, 2003

Chappelle keeps getting offered roles in the same upcoming 2004 film: "The only movie they kept offering me over and over was fuckin' Soul Plane," he told Esquire. "They kept giving me the script and I'd say, 'I passed on this script.' And it would just keep coming back. No, I don't want to do Soul Plane!" Meanwhile, he used his sketch, "The Mad Real World" to mock the way his friend Dave Edwards, a black comedian, was kicked off MTV's The Real World. Chappelle's sketch reversed the premise so that a white guy is driven crazy by black roommates and kicked out when one says, "I don't feel safe" — the same words used to justify the firing of Edwards.

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February 11, 2004

During Season Two, Chappelle's Show airs a "Charlie Murphy's True Hollywood Stories" edition featuring a story about "habitual line stepper" Rick James, drunkenly bartending, fighting with Murphy, and shouting the catchphrase that would come to torment Chappelle: "I'm Rick James, bitch!" It was the only episode of the show to air with a disclaimer, due to Comedy Central's concerns about the use of the N-word, Chappelle told Esquire: "They gave us the notes and there were like 46 or some insane number of bleeps that we would've had to put over it.… So now I'm sitting in a room, again, with some white people, explaining why they say the N-word." By June 2004, the catchphrase has become so annoying that Chappelle walks off stage at a stand-up gig in Sacramento, saying, "The show is ruining my life."

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April 7, 2004

In Season Two, Paul Mooney, as Negrodamus, mocks Wayne Brady, saying, "White people like Wayne Brady because he makes Bryant Gumbel look like Malcolm X." Chappelle found out that Brady's feelings were hurt, so he creates a new skit, based on Training Day. Brady plays the badass who feeds drugs to a cowering Chappelle, perpetrates drive-by shootings, and yells, "Is Wayne Brady gonna have to choke a bitch?"

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September 4, 2004

Showtime airs Dave Chappelle's stand-up special For What It's Worth. Recorded at San Francisco's Fillmore, it earns two Emmy nominations. The routine includes a devastating riff on speaking to high-school students: "You've got to focus! You've got to stop blaming white people for your problems! You've got to learn how to rap or play basketball… Either that, or sell crack. That's the only way I've seen it work."

And he unleashes a viciously self-aware riff about Michael Jackson. "He's a freak," Chappelle says. "Just remember — that when you look at that thing that he calls his face, that he did that for you somehow. Somehow, he thought maybe it will help… if I turn myself into a white — I don't know what the fuck it is — ghoulish creature. He did it for you." Then Chappelle announces that he's also going to get some work done: he's going to Botox the wrinkles out on his balls. 

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September 18, 2004

Inspired by the 1973 concert documentary Wattstax, Chappelle throws a block party in Brooklyn. Dave Chappelle's Block Party, shot in Brooklyn and directed by music-video guru Michel Gondry, will later premiere at the 2005 Toronto International Film Festival, gross almost $12 million theatrically in 2006, and more than double that revenue on DVD ($19 million). The film mixes Chappelle's stand-up, interviews with local characters, and performances by Erykah Badu, Mos Def, Talib Kweli, Dead Prez, Jill Scott, Kanye West, and The Roots, several of whom will accompany Chappelle on his current concert run. 

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September to October, 2004

On September 18, Chappelle signs a deal for $55 million, plus half of all the revenue from DVD sales, which might have pushed the deal into nine figures. He tells Entertainment Weekly, "What this money really purchased me was a certain peace of mind. It was an affirmation, just to be confident in your intuition.'' In October, Comedy Central announces that Chappelle's Show: Season One: Uncensored has sold more DVD's than any television show in history, topping The Simpsons. But Chappelle and show co-creator Neal Brennan are at odds and drifting further apart. Brennan would later say that Comedy Central "poisoned" their relationship by separating the two and negotiating with Chappelle first. 

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2004-2005

Chappelle begins taping season three. Reflecting the comedian's unease, the premiere is titled, "$55 Million & Getting Revenge." In the second sketch, he's charged $11,000 for a haircut.

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May 4, 2005

While promos for the third season air on Comedy Central, the network announces that the season will not proceed as scheduled. Entertainment Weekly reports that "on April 28, the comedian flew from Newark airport to South Africa to check himself into a mental health facility," adding that "his publicist has repeatedly denied persistent rumors of drug use." Rumors swirl: Is it because he's a drug addict? A Muslim? Suicidal? A drug-addicted, suicidal, Muslim spoiled celebrity? In the May 15 issue of Time, Chappelle denied all the baseless rumors, including reports of a mental-health facility: "Let me tell you the things I can do here which I can't at home: think, eat, sleep, laugh," he said. "I'm an introspective dude. I enjoy my own thoughts sometimes. And I've been doing a lot of thinking here." He mocks the drug accusations: "Why do I live on a farm in Ohio? To support my partying lifestyle?…I want to make sure I'm dancing and not shuffling."

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2006

Dave does Oprah, telling her that he finds it suspicious that all black comedians end up having to wear a dress to get laughs. Explaining his disappearance, he says, "I wasn't crazy, but it is incredibly stressful." He says he was "deliberately being put through stress" by the network and that people "were trying to control me … I would go to work on the show and I felt awful every day… I felt like some kind of prostitute or something." Chappelle also blames himself, framing the dissolution of the show as a result of his own unresolved self-contradictions: "I was doing sketches that were funny but socially irresponsible."

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2008-2010

Chappelle surfaces in comedy clubs from time to time, performing stand-up without advance notice. Then, in 2008, Chappelle attempts to set the world-record for on-stage stand-up comedy endurance at Hollywood's Laugh Factory. He works the crowd for five hours before finally taking a bathroom break, which disqualifies him. "There are only two rules," club's owner Jamie Masada told reporters. "You have to continuously tell jokes that are funny and you can't leave the stage, even to go to the bathroom." Dane Cook's seven-hour, 34-minute record still stands. In 2010, Chappelle does a stand-up set at Los Angeles's Laugh Factory and, due to pent-up demand, the short video tops five million views. 

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July 2011

Chappelle performs at a Summer Groove charity event in Miami and becomes so upset by one audience member filming his show that he stands on stage, rarely speaking, for a reported 45 minutes. According to local TV host Roland S Martin's Twitter feed, Chappelle calls it "a test of wills" and says, "As shitty as the show is, I can't wait to explain this on CNN."

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2013

The excitement around Chappelle's re-emergence in unannounced stand-up sets reaches a fever pitch in February at New York's Comedy Cellar, where he's joined one night by Chris Rock, Bill Bellamy, Kevin Hart, Questlove, and Marlon Wayans. Hart tells GQ, "It was the highlight of my life." In June, he announces that he will co-headline the Oddball Comedy & Curiosity Festival with various guests. Then, in August, Prince releases the single Breakfast Can Wait, featuring Chappelle, dressed as Prince on the cover, teasing it with the tweet: "Game: Blouses." All appears well. Then, 11 days after the Prince tweet, during a performance in Hartford, Chappelle is heckled and walks off the stage. "You are booing yourself. I want you to go home and look in the mirror and say 'Boo! ' That's how I feel about you."

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