How long has it been since Dave Chappelle left his Comedy Central series, Chappelle’s Show?
Long enough that in his first appearance on Late Show with David Letterman in a decade, Chappelle joked to Letterman that he just says to Comedy Central that he hasn’t quit. “I am seven years late for work.” Which would have been a valid excuse three years ago? But since it has been so long since the events that transpired in 2004, and because we haven’t seen Chappelle collectively as a national broadcast network-watching audience since then, Letterman had him revisit the whole saga once more.
Chappelle is back in our hearts and minds this month, and in New York City specifically, because he’s performing a weeklong run at Radio City Music Hall — June 18-26, 2014 — with a few shows performing solo stand-up, then a few shows backed by a full orchestra and special musical guests, including The Roots, Erykah Badu, Janelle Monae, Busta Rhymes and more.
Roll the clip!
Here’s the full interview, which starts with Chappelle and Letterman trading middle names, talk about Chappelle’s first time performing at Radio City — he was 19, and opening for Aretha Franklin — and their mutual experiences with bombing. Letterman said, “I have been on more bombing runs than The Enola Gay.” Chappelle countered: “I’m of the belief that the best comedians bomb hard. When they bomb, they bomb hard. You take chances. Sometimes you fall flat. Sometimes you do great. My favorite comedians did that.” They also share stories about fatherhood. Chappelle’s kids are 13, 11 and 5. Letterman always loves hearing advice from others to apply to his own son.