Dave Chappelle Finally Explains Where He Went After He Bailed On Comedy Central

Dave Chappelle on The Late Show with David Letterman June 2014While most of us know that Dave Chappelle walked away from an extremely lucrative, multi-million dollar deal at Comedy Central, very few of us actually know why, because he doesn’t like to talk about it. But he opened up to Dave Letterman last night, giving us some of the first insight into his decisions that anyone has gotten in seven years.

The third season of Chappelle’s Show was set to premiere in February 2005, but was pushed back due to delays and then canceled altogether after Dave abruptly left the show, walking away from an undisclosed amount of money for reasons that he’s hinted at over the years — chiefly that he didn’t like how fame was influencing his fan base.

But in his first appearance on The Late Show in ten years, after first saying that he doesn’t talk about what happened, Chappelle proceeded to do just that, explaining why he made the decision to quit one of the most successful shows and most lucrative deals to ever come through Comedy Central. But first things first? He didn’t quit. . first appearance on the show in ten years.

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

But Letterman kept pressing, and finally the details started to eke out. Rumors were swirling that Chappelle had moved to Africa full time for psychiatric treatment or some other hospitalization, but Chappelle says he was only there for a matter of weeks, and it was purely to hide.

“I was there for two weeks. There’s not too many good hiding places left in America. [...] It was like living in the corner of perception and reality, y’know what I mean? It’s a weird place to be. When everyone thought Wesley Snipes was in jail, I saw him at a party.”

He does throw jokes like this in there every once in a while, but for the most part, the interview is extremely unguarded and open, an extreme rarity for Chappelle.

“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.”

To turn your back on millions of dollars, you’d certainly have to have a different perspective than most people, but Chappelle makes the excellent point that between someone who has $10 million and someone who has $50 million, there are very few differences in lifestyle — just ‘an astounding $40 million’, which seems to be the amount he was suggesting he was to be paid for subsequent seasons of Chappelle’s Show. Asked now if he regrets his choices then, he answered:

“Of course I would like to have that money, [but] it’s a very complicated answer. Money is the fuel for choices. Money gives me choices. So that’s not nothing, it’s something. I can choose where I want my kids to go to school. I can choose where I want to eat in a given day. But it’s not the end-all, be-all. There are other things in my life that are not purchased with money that are very valuable.”

LEtterman points out that even if Chappelle had the money, there’s no way to know whether he’d be a better person or a happier person, to which Chappelle very candidly responds:

“I think I might be a happier person.”

Biiiig audience laugh, because it’s honestly a relief to know that Chappelle is a human being like us, and still thinks about that money sometimes and wonders if he made the right choice:

“I don’t know…there’s no way of knowing. But y’know, sometimes I listen to a Jay Z record and it starts making me feel bad about the choices I’ve made. This guy’s had more fun on two songs than I’ve had in the last eleven years.”

Haaaa. That’s great. But no matter how Chappelle feels about it, I think the main thing that everyone’s so excited about is just him being around again. He hadn’t done a late night show since 2008, and now he’s not only back, but promoting his nine dates at Radio City Music Hall.

Here’s hoping he makes it through the whole thing and that nobody shouts ‘I’m Rick James, bitch!’ at him. This is why we can’t have nice things…

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    • Isabelle

      I think he was interviewed about this a few years ago. I remember him commenting on it. It might have been Oprah or some special about him.