David Letterman, Dave Chappelle


"I don't talk about it."

Until now!

Dave Chappelle is finally opening up about the abrupt ending of Chappelle's Show, his hit Comedy Central series that he infamously walked away from in 2005. The comedian stopped by Late Show with David Letterman on Tuesday night, where he opened up about leaving Chappelle's Show midway through its third season.

"Listen, here it is. Technically, I never quit. I'm seven years late for work," Chappelle joked.

After walking away from the show, Chappelle took off to South Africa, something Letterman asked the reclusive comedian about. "I was there for two weeks," Chappelle clarified, before joking, "I mean, there's not too many good hiding places left in America." 

Letterman then pressed Chappelle about accepting, and then eventually turning down, the "enormous sum of money to continue doing the show" that Comedy Central offered after the first two successful seasons of Chappelle's Show. (The deal was reported to be worth $50 million.)

"It's very hard to go through something like this because no one's really done it before. There's not too many people who don't think I'm crazy," Chappelle said. "I look at it like this: I'm at a restaurant with my wife, we're at a nice restaurant, we're eating dinner. I look across the room, I say, 'You see this guy over here? He has $100 million and we're eating the same entree.' So OK, fine, I don't have $50 million or whatever it was. But say I have $10 million in the bank. The difference in lifestyle is miniscule. The only difference between having $10 million and $50 million is an astounding $40 million."

He then added, "Of course, I would like to have that money."

Chappelle, who made a rare appearance on Late Show to promote his sold-out stand-up run at Radio City Music Hall from June 18-22, as well as a limited residency from June 24-26 alongside musicians such as The Roots and Busta Rhymes, admitted he may regret some of the choices he made when it came to the end of Chappelle's Show.

"It's a very complicated answer," he hedged, saying he "might be a happier person" if he stuck with the show...and kept the $40 million, of course. "There's no way of knowing."

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