More than a decade after its premiere, Chappelle’s Show has entered the realm of show business mythology. It’s not always clear, though, which mythical figure Dave Chappelle most resembles. Is he Icarus, who flew too close to the sun and flamed out? Or Sisyphus, exhausted by the effort of pushing a boulder up a hill that was constantly trying to drag him down? Questions have always haunted the show’s sudden demise, chief among them: What caused Dave Chappelle to walk away from critical success, widespread cultural influence, and a deal worth $50 million dollars?
Those questions, and the dissolution of Chappelle’s partnership with series co-creator Neal Brennan, are the subject of a found-footage documentary assembled by amateur editor Brandon Farley. According to Vulture, Dave Chappelle: The 50 Million Dollar Question was originally posted on YouTube last year, only to be pulled down. The two-hour piece has recently been re-uploaded on Vimeo, possibly as a result of renewed interest in the comedian after Chappelle’s successful Radio City Music Hall shows, as well as his recent appearance on The Late Show With David Letterman.
The documentary uses footage from multiple sources, including the difficult interview Chappelle conducted with Oprah shortly after his return from the two-week sojourn in South Africa that marked his break from the show, as well as his 2006 episode of Inside The Actors Studio. Brennan’s side of the story mostly comes from a 2012 episode of Joe Rogan’s podcast, in which the writer and comedian discussed at length the breakdown of his friendship with Chappelle, and the way corporate interests at Comedy Central encouraged the fracturing of their partnership.
The documentary doesn’t hope to provide any concrete answers to the enduring mystery of Chappelle’s retreat from the spotlight, but it does paint an intriguing picture—in the man’s own words—of a young, brilliant comedian suddenly forced to be the spokesman for his brand, his network, and his race, and the incredible pressures that came with it.
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