WATCH: Dave Chappelle Talks About Leaving Chappelle’s Show On Letterman

Dave Chappelle walked away from the ludicrously successful Chappelle’s Show for a myriad of different reasons, depending on what you read or who you believe. Be it for feeling disenfranchised with a corporate machine devaluing his art, or if he felt uncomfortable working in any format that wasn’t pure stand-up, or an illuminati of black celebrities conspired to bring him down and destroy his character, whatever the reason, the leaving was spectacular.

Seldom has Dave talked about the show in any depth since, and in fact his public profile has shrunk considerably with the notoriously private man choosing to lead as quiet a life as possible, out of the public eye whenever he can. But, inevitably, he does show up from time to time and the issue remains one of great interest.
So Dave stopped by another Dave’s work as a guest on the Late Show with David Letterman. And, true to form, Letterman began prodding him with softball questions about walking away from a reported $50 million contract with Comedy Central.
Be warned, this isn’t going to offer any groundbreaking insights into Chappelle’s mindset, or any ideological clashes he may or may not have had with Comedy Central. What it will do is treat the media’s ability to leap on any small issue with a tongue-in-cheek attitude.
Enlightening? Not really. Typically dryly hilarious? You betcha.