Last night (June 10), Dave Chappelle appeared on Late Show with David Letterman almost a week in advance of his run of stand up comedy shows and a Block Party reunion show with The Roots, Erykah Badu, and more in New York City. The duo discussed a few topics, but none more prevalent than the elephant in the room — his abrupt exit from Chappelle’s Show a decade ago.
Dressed to the nines, the comedian had some honest discourse with Letterman, but not without a few quips here and there. “Here it is. Technically, I never quit. I’m seven years left for work,” said Chappelle, referencing how he walked about from a $50 million pay day.
“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,” he continued.
Chappelle seemed conflicted at times, but that’s often been an underlying them in his comedic routines. But in a moment of honesty, he revealed that he might be happier had he taken the money.
“There’s no way of knowing,” Chappelle responded to Letterman’s questions about happiness. “But sometimes, I listen to a Jay Z record and it starts making me feel bad about some of the choices I’ve made. This guy’s had more fun on two songs than I’ve had in the last 11 years.”
Peep what Dave Chappelle had to say in the footage below. Share your thoughts in the comments.