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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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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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