Dave Chappelle Tells Letterman He Does Has Some Regrets Over Leaving His Show Behind, Especially the $50 Million

By Vivian Kane | Videos | June 11, 2014 |

By Vivian Kane | Videos | June 11, 2014 |

Dave Chappelle was on Letterman’s Late Show for the first time in 10 years last night. The conversation between the Daves went to the obvious place. Dave 1 asked Dave 2 what the deal was with Dave 2 peacing out to South Africa back in 2005, and Dave 2’s response was perfect, saying, “Technically, I never quit. I’m seven years late for work.”

Which, one might hope, is a not so subtle hint that he’s finally made his way back to the office.

In the full interview, however, Dave pressed him further and Chappelle admitted that he does have some regrets, mostly over the money he lost (starting around the 7 minute mark):

It’s very hard to go to someone like this because no one has done this before. So there’s not too many people who don’t think I’m crazy. I look at like this: I’m at a restaurant with my wife, its a nice restaurant and we’re eating dinner. I look across the room and say, ‘You see this guy across the room. He has $100 million dollars, and we’re eating the same entree. Ok, fine, I don’t have $50 million dollars or whatever. Let’s say I have $10 million in the bank, the only difference between having $10 million dollars and $50 million dollars is an astounding $40 million dollars.

Then again, he says, it’s not really about the integrity, either. It was just a choice, and he still wishes he had some of that $50 million.

“I go home and make the kids some integrity sandwiches … it makes no sense at all. There’s nothing anyone can say. It’s just you do what you feel like you need to do. It’s a very complicated answer because I felt a variety of ways over the last years. Whenever there’s something I’d like to have that I could have afford but I can’t now afford, then I’m upset about it. But then when I see a guy who goes to a job that’s time consuming and he doesn’t have free time to do things I get to do, then I feel good about it … Money is the fuel for choices. Money gives me choices. It’s not nothing. It’s something … there are other things in my life that I do not purchase with money that are very valuable.”

With the extra $40 million, though, he does say he’d probably be happier, adding “Sometimes I listen to a Jay Z record and starts making me feel bad about some of the choices I’ve made. This guy has had more fun on two songs than I’ve had over the last 11 years.”