Dave Chappelle: “Sometimes I Listen To A Jay Z Record And Feel Bad About Some Of The Choices I Made”

06.11.14 4 years ago 33 Comments
dave chappelle david letterman


“Technically, I never quit. I’m seven years late for work.”

Comedy has always been a gateway into intense introspection. It’s been like that for every great comedian from Richard Pryor, Bernie Mac, Eddie Murphy, Patrice O’Neal and more. It’s been especially true for Dave Chappelle. Last night, the enigmatic and (for the better part of a decade) secretive comedian stopped by David Letterman’s late night gig.

The appearance was a scarce one for Dave who has kept public appearances to a minimum since walking away from his robust $50M contract extension with Comedy Central. And naturally, the topic came up. Letterman, like the great majority of Dave fans, simply asked why. Chappelle’s tone and response, for the first time to my knowledge, suggested genuine regretfulness of the decision.

“It’s very hard to go through something like this because no one’s really done it before. So there’s not too many people that don’t think I’m crazy, right? So, I look at it like this.

I’m at a restaurant with my wife. It’s a nice restaurant we’re eating dinner. I look across the room and say, ‘You see this guy over here across the room? He has $100M.’ And we’re eating the same entree. So, ok, fine. I don’t have $50M or whatever it was, but say I have $10M in the bank. The difference in lifestyle is miniscule. The only difference between having $10M and $50M…is an astounding $40M.

Of course I would like to have that money. When you quit, my friends’ll try and make me feel better but no one’s been through that so they’ll say stupid stuff – not stupid stuff, it’s nice – ‘Well, you know what Dave, at the end of the day, you still have your integrity.’

Yeah, that’s great. I’ll go home and make the kids some integrity sandwiches.”

Time allows for reflection. Yet, his response here varies from what he explained to the late Dr. Maya Angelou in 2006.

The entire 15-minute clip is well-worth the watch as the two discuss much more than Dave’s prolonged and head-scratching resignation from the world of entertainment, such as Dave’s crash-and-burn memory doing standup at Radio City Music Hall opening for Aretha Franklin at 19 and life as a father. Come June 23, Chappelle will be performing alongside Nas and a 45-piece orchestra at RCMH (falling directly in the middle of a marathon of dates between June 18-26).

Whether this signifies “the return of Dave Chappelle” or simply a flash in the pan type of resurgence, it’s just soothing to see a comedian much of my generation grew up on (publicly) happy again.

Related: Dave Chappelle: Inside The Actors Studio

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