Chappelle is the best stand-up ever

OPINION: Chappelle is the best stand-up ever. I know we just said that, but you know it's true.

"Dave Chappelle: Untitled" - UK Premiere - Red Carpet Arrivals
LONDON, ENGLAND - OCTOBER 17: (EDITORS NOTE - This image has been converted to black and white) Dave Chappelle attends the UK premiere of "Dave Chappelle: Untitled" at Cineworld Leicester Square on October 17, 2021 in London, England. (Photo by Eamonn M. McCormack/Getty Images) ()
LONDON, ENGLAND - OCTOBER 17: (EDITORS NOTE - This image has been converted to black and white) Dave Chappelle attends the UK premiere of "Dave Chappelle: Untitled" at Cineworld Leicester Square on October 17, 2021 in London, England. (Photo by Eamonn M. McCormack/Getty Images)

Editor’s note: The following article is an op-ed, and the views expressed are the author’s own. Read more opinions on theGrio.

It’s as hard to capture the genius of Dave Chappelle in a short essay as it is to explain the genius of Prince or Miles Davis. These are book-length challenges. But let’s try. 

Where most comics deal in short bursts of sentences. Chappelle tells long, winding stories that draw you in and keep you on the edge of your seat. He mixes social commentary into his comedy, giving intellectual observations about the world while keeping you laughing. He makes you feel smart for getting his comedy. And he talks a lot about himself in a way that creates a world—you know who the person speaking to you is. I can always go to a comedy show and walk away with a few funny jokes I can tell except if I go see Dave. You can’t repeat his long stories and remember all the callbacks and references. And because so much of his comedy is about himself, how could you tell the joke yourself? 

I love it when Chappelle, befitting someone in the hip-hop generation, talks about “Chappelle,” a version of himself who is brilliant, rich and such an amazing comedian that he can make a punchline out of anything, but also someone who’s lazy and liable to quit doing something, anything, at a moment’s notice. Chappelle is unapologetically Black—his comedy is Blackcentric and takes full advantage of the ability to make fun of white people and to call out their mistakes. In the way he talks and how he lives his life, Chappelle seems to be free. 

Years ago, I saw Chappelle perform in Connecticut, days after a show in Detroit had gone badly, and he came out and recounted the story of the bad show and said that he might leave us, too. Like, hey, you never know. It felt like he was someone who was so liberated that he was comfortable walking away from anything if he was uncomfortable. I know Chappelle will walk away from anything because he once walked away from me.

In 2005, after Dave Chappelle’s Block Party came out, I flew to Ohio to interview Chappelle for BET. This was after he’d famously quit the legendary Chappelle’s Show. I was asked not to ask about Chappelle’s Show. Of course, I was there to do just that. After 10 minutes of talking about the Block Party, I segued into the brilliance of Chappelle’s Show and how great it was. He seemed uncomfortable at the shift, but I was focused on the show’s greatness, so he let me go there. Then, after 10 minutes of talking about the genius of his show, I asked him about leaving. He shifted uncomfortably in his chair. He lowered his gaze to the floor. He started talking about how we had seen this sort of thing before—he said after Mariah Carey and Martin Lawrence had gotten gigantic deals, they, too, had lost their minds and had public meltdowns. I felt like a therapist on the verge of a breakthrough. 

I had to ask just a few more questions about him leaving—one of the central cultural events of my generation—but one of my two cameramen announced that we had to stop for a moment because he had to change his battery. Are you kidding? He should have recognized that we were in a delicate moment and done this silently, but no, in an act of total tone-deafness, he announced that we had to stop. As soon as he said it, Chappelle said he needed a cigarette and leaped up from his chair. He walked outside and never came back. As painful as that was personally, I respect Chappelle immensely for being the sort of person who will walk out. In his post-Chappelle’s Show comedy, he talks a lot about refusing to be controlled by capitalism and the institutions that dominate it. He has likened Hollywood to a pimp, making himself a potential prostitute, as a way of explaining why he’s refused to play its game. He publicly called out Netflix, who has paid him about a zillion dollars over the past decade, for streaming Chappelle’s Show when he thought the deal was unfair. Chappelle is fearless onstage and off, willing to sacrifice a lot of money for his freedom and his mental health. I respect the hell out of that. I’m not saying I would’ve done it, but I understand. 

I think Chappelle’s best standup hour is still “The Age of Spin” because its structure is so brilliant. It’s like there are two countermelodies or counter-rhythms playing off each other as he goes in and out of stories about O.J. Simpson, commentary on Bill Cosby and notes on himself. But all of Dave’s specials have been great. He’s got a long, incredible resume of taking comedy into new realms and to me, the comedy GOAT battle is between Chappelle and Richard Pryor. No one else is close to them. There are a lot of similarities between them—Pryor, too, loved great stories. He often added bits of social commentary and talked a lot about himself. Both guys are unapologetically Black and champions for Black people. I have listened to a ton of Pryor’s stand-up work, and I revere him immensely. I love Pryor but I think Chappelle is funnier. I think he’s the greatest of all time.


Touré is a host and Creative Director at theGrio. He is the host of the podcast “Toure Show” and the podcast docuseries “Who Was Prince?” He is also the author of seven books, including the Prince biography Nothing Compares 2 U. Look out for his upcoming podcast Being Black In the 80s.

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