It was May 2005, and Dave Chappelle was at the peak of his fame. He had two decades of standup comedy under his belt, a record-breaking television show, and a $50 million contract to go along with it all.
But all was not well. Chappelle was a Pagliacci; a clown whose emblematic smile hid uncertainty, and a festering dislike for the industry.
So he walked away.
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Dave Chappelle was born in Washington D.C., on August 24, 1973. His parents, both professors, were politically active, and the house was often filled with notable people including jazz artist Johnny Hartman, who first recognised his comedic talent.
“I was the funny dude. I was real comfortable with adults. I was cutting up in front of Hartman and he was like, ‘Man, you’re a funny kid.’ And he says to me, ‘You’re gonna be a comedian.’ And I was like, ‘What’s a comedian?’ And he’s like, ‘It’s a guy who tells funny stories for a living, like Richard Pryor or Redd Foxx.’ I said, ‘I want to be a doctor.’ And he was like, ‘Eh–‘,” he recalled to Esquire.
Soon after, Chappelle started watching the likes of Pryor and, later, Eddie Murphy, and became inspired. By his teens, he was the life of the party. Friends would remark that life was never as fun when he wasn’t around.
So it was decided: he was going to be a comedian.
While he was still young, Chappelle’s parents separated, and he remained with his mother to study at the Duke Ellington School of the Arts, where he studied theatre.
Graduating in 1991, Chappelle moved to New York to pursue his career. His first performance came as part of the Apollo Theater’s Amateur Night. Summoning his courage, he took the stage, only to be booed off. Instead of letting the experience deter him, however, Chappelle was inspired to strive even harder as a result.
Within a year, he was making a prominent name for himself on the comedy circuit, and could often be found performing in public parks for the experience. He made his film debut that same year in Mel Brooks’ Robin Hood: Men in Tights. Chappelle was offered the role of Bubba in Forrest Gump, but turned it down, fearing that the part could be conceived as demeaning and racist. In 1997, he would parody the film for his short, Bowl of Pork.
By age 19, he was opening for Aretha Franklin.
It wasn’t long before Chappelle was garnering the attention of TV network executives. While they worked on developing a series for him, ABC cast him alongside friend Jim Breuer to appear on Home Improvement. Their performance was so popular that the characters received a spin-off, Buddies, but Breuer was fired after the pilot, and the first season failed to gain any traction.
Chappelle tried his hand at TV once again in 1996, with a sitcom entitled Dave Chappelle. “They fly me out for a creative meeting. I’m in a room full of white people, and they proceed to tell me why we need more white people on the show, so it can have a more universal appeal,” he told Variety. “This network built itself on black viewers, and what they’re saying is white people are narcissistic. They don’t want to watch black people, they want to watch themselves. It tells every black artist no matter what you do, you need whites to succeed.”
“It’s disgusting, and it made me want to vomit.”
When his father died soon after, and he travelled to Ohio for the funeral, Chappelle considered leaving the business. It wouldn’t be the last time.
Eventually, he did return, making an appearance in Eddie Murphy’s remake of The Nutty Professor. It was the start of a range of success across film and television, culminating in the production of Half Baked, a stoner comedy which he co-wrote alongside Neal Brennan. It would become a box office success, and a classic of the subgenre.
In 2003, at the age of 29, Chappelle debuted Chappelle’s Show, a weekly sketch show on Comedy Central. It would launch him to superstar status internationally.
A parody of American culture, and a celebration of predominantly black entertainers often overlooked by a white-dominant market, Chappelle’s Show was such an enormous success that parent company Viacom offered him a $55 million contract, including a share of DVD sales, for two more seasons. Though Chappelle knew that the intense workload would mean focusing less on standup and more on sketches, which he didn’t particularly enjoy, but he accepted the offer regardless.
Production of season two went smoothly, producing such iconic scenes as A Moment in the Life of Lil Jon, True Hollywood Stories – Rick James, and Wayne Brady’s Show.
All was not well with Chappelle, however. Two months after the season aired, he was performing in Sacramento, California, and ended up walking off-stage due to the audience constantly shouting “I’m Rick James, bitch”, in reference to the True Hollywood Stories sketch.
He returned after a few minutes and declared “the show is ruining my life”.
“People can’t distinguish between what’s real and fake. This ain’t a TV show. You’re not watching Comedy Central. I’m real up here talking,” he said, making it abundantly clear how success was causing his fans to treat him less and less like an individual, and more like some kind of construction for their entertainment.
In May of the next year, season three was scheduled to air, but Chappelle was at wit’s end. In one sketch, he was playing a pixie in ‘black face’, when a white member of the crew suddenly “laughed in such a way—I know the difference of people laughing with me and people laughing at me—and it was the first time I had ever gotten a laugh that I was uncomfortable with. Not just uncomfortable, but like, should I fire this person?” he told Oprah in a 2006 interview.
He needed to refocus, and rebalance. In the middle of production, he left, and went to South Africa without a word.
Media speculation was quick to flair. Was Chappelle crazy? Did he have a drug addiction? It was what he kind of expected. “When I see that they put every black man in the movies in a dress at some point in their career, I start connecting the dots,” he said, in regards to the industry’s recognition of black entertainers.
He’d left the show for good, and relocated to a farm in Ohio with his family, but Chappelle continued to work as a comedian, even as he attempted to keep out of the spotlight. He starred and produced in Dave Chappelle’s Block Party, a documentary about the free concert he hosted in Brooklyn on September 18, 2004.
Chappelle appeared on Def Poetry, was interviewed for Inside the Actors Studio, and even acted as the show’s interviewer when normal presenter James Lipton became the subject.
In 2005, Chappelle’s Show launched on DVD, and became the highest-selling TV series set of all time, beating out the likes of The Simpsons, Seinfeld, and Friends.
Today, Chappelle mostly makes impromptu appearances at comedy venues, though sometimes does major events such as headlining the Oddball Comedy & Curiosity festival alongside Flight of the Conchords.
Though he is not as proactive as he once was, Chappelle’s legacy is unmistakable. He has been called the greatest comedian of all times by the likes of colleague Kevin Hart, and Billboard magazine.
Interestingly, Prince took an image of Chappelle impersonating him and used it as the cover art for his single, Breakfast Can Wait. Perhaps this act, committed by an artist who so firmly strived to protect his image, is all the proof needed to confirm Chappelle’s influence on not just comedy, but the international community.