Most times, when an entertainer announces their retirement, they really mean, “Press please. PS: I am already planning my comeback.” But Dave Chappelle was never anything but sincere. So, unfortunately, after he revealed that he wouldn’t be returning to “Chappelle’s Show” and needed a break from the business of show, he all but disappeared.
Sure, he’s since popped up in a few places, namely “Inside the Actor’s Studio”. Unlike many guests who speak pretentiously of “the craft” and bask in James Lipton’s sycophantic line of questioning, Chappelle was completely himself. That is to say he was honest, open, humble and naturally hilarious. He spoke candidly about why he bailed. He was not made for corporate whoredom. He feared he was losing touch with the original intentions of the show. “The hardest thing to do is to be true to yourself,” he lamented. “Especially when everybody is watching.”
About why he bailed to Africa, he explained, “Coming here I don’t have the distractions of fame. It quiets the ego down. I’m interested in the kind of person I’ve got to become. I want to be well rounded and the industry is a place of extremes. I want to be well balanced. I’ve got to check my intentions, man.”
How many famous entertainers are that introspective? Not fucking many.
On “Actor’s Studio”, he also talks about the money. He’d already made buckets of dough for “Chappelle’s Show” when the studio offered him a $55 million contract to continue cranking out the hits. That’s a lot of money. It may not sound like it in the context of television and film because we’re so used to enormous budgets and ridiculous salary wars. The rich and famous convince themselves they deserve it. But what the hell would the average, one-car, one-mortgage American do with that kind of cheddar? You could buy fancy toys, expensive dinners and completely lose touch with reality. Or you could cut out and recognize that you have an opportunity to do something that will help others and make them feel good. And that’s what Dave Chappelle did.
He’s not the first guy to use his money to help people. But he’s certainly one of the only famous people to do so without all the self-congratulatory smugness of, say, Bono.
I was really depressed the day I saw “Dave Chappelle’s Block Party”. I’d just been through a breakup and a career setback and was feeling pretty lost myself. But I cried tears of joy whilst watching that film. I left that theater completely uplifted. The premise is simple: Chappelle uses his own money and connections to throw the block party of a lifetime in a small Brooklyn neighborhood. He pads the bill with Kanye West, Mos Def, Erykah Badu, the Roots, and even manages to reunite the Fugees. Many of these acts are known for their egos. You could easily pay $100 to see any of them individually, but somehow, through his charisma and general goodness, Chappelle convinces them to perform for free.
Whilst preparing for the block party, Chappelle wanders around the small Ohio town where he lives, talking to the locals and inviting them to the show. He invites folks from all walks of life, from the old man who runs the menswear shop to the Ohio State University marching band. He also offers to pay for their transportation to the show. The result is an incredible melting pot of people celebrating life and music together. It’s not about money and it’s certainly not about fame and status. It’s just a big-assed party. It’s the closest anyone has ever come to recreating Woodstock (and not that corporate-branded bullshit from 1994, either). One day of peace and music.
This is why we need Dave Chappelle. There are those that don’t fully comprehend his significance. His recurring characters became clichés. The frat boys shouting, “I’m Rick James, bitch,” certainly contributed to his brief meltdown. But his comedy turned the mirror on American culture in a very accessible way. He poured a little sugar on those moral Cheerios. He was making Hollywood a better place. And then he left us.
I understand that he needed to get back in touch with himself. I’m glad he got out before he went crazy or lost sight of his goals. But I really hope he doesn’t stay away long.
Maybe if we all clap our hands and believe, we can bring Dave Chappelle back.
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Effed by the Wind 
I have to say this is the most thoughtful take I’ve read on this. Usually people brand it crazy to walk away from 50 mill but I felt like I totally got why he did it, and I think you did too.
i actually really miss dave chappelle a lot, too. its been forever since he’s done something. i got into the show after he stopped doing it, but he’s my favorite comedian and now that i think of it, he really is one of the smartest, most generous and self-aware celebrities out there. theres not many who would turn down 55 million, seinfeld turned down at least 10 million, and others have done it too, but 55 million is a lot more and dave could have been one of the biggest names known. i really hope he returns soon, i check in on wikipedia every few weeks or months to see if he’s back or coming up with a new idea or a movie or something. i think i might write him a letter. BRING DAVE BACK!