Why Dave Chappelle Walked Away… “The $50 Million Dollar Question”

Dave Chappelle has finally began to resurface across mainstream media outlets and yes, he has been missed. He first appeared on David Letterman opening up a little bit about why he walked away from Chappelle’s Show. He later appeared on Jimmy Fallon joking about his first time meeting Kanye West. Already his one-liner’s are spreading throughout social networks.

It is apparent that he is promoting his shows at Radio City Music Hall which end this Friday (6/27) but what can we expect to come after that? Since 2005, everyone still wonders why he walked away from the $50 Million and speculated that his departure was driven by drug addiction or some other contrived mental health issues. Who the hell would walk away from $50 Million Dollars…. right?

This may just be an amateur documentary by Mischief Maker Productions but it is a damn good one. It spans over 2 hours but tells a compelling story building up to the creation of Chappelle’s Show and what lead to his departure. Even if you watch only parts of this documentary, you will get a glimpse of what drove Chappelle to abandon the $50 Million and you will no longer think he is crazy for doing it.

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. – The AV Club

The looming question on everyone’s mind is, Will Chappelle’s Show ever return? I have my suspicions that something big is in the works.

By: Pat Hanavan