The 20 Best 'Chappelle's Show' Sketches, Ranked - Maxim

The 20 Best 'Chappelle's Show' Sketches, Ranked

Which classic Chappelle sketch is your favorite?
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Dave Chappelle as Prince

Dave Chappelle as Prince

In recent years, Dave Chappelle has reemerged from his self-imposed exile looking impressively buff and doing some totally killer—and definitely controversial—new stand-up material.

That includes his recent Netflix specials, Equanimity & The Bird Revelation. In those routines before large audiences he's very much the Chappelle of old, completely unafraid of tackling controversial subjects in typically blunt, hilarious style. 

No one can forget why we care that the man is back. In just 33 episodes that ran on Comedy Central between 2003 and 2006, Chappelle and co-writer Neal Brennan turned out some of the greatest sketch comedy in television history. Then Chappelle took his money and ran for a while, stayed off the radar. 

Any ranking of the greatest episodes from a show as legendary as Chappelle's will be subject to controversy—everyone has their own list and order. 

But I decided to commit to making this list anyway, partly just as an excuse to re-watch the videos. Here's my personal top 20 Chappelle's Show sketches ranked for originality and—obviously—hilarity.

20. If the Internet Were a Real Place

The internet in the early 2000s was very different from today—but somehow this sketch still feels absolutely true. Except for receiving your porn fix directly from Ron Jeremy himself. That still feels a little unrealistic.

19. Trading Spouses

Chappelle was often at his best when riffing on cultural contrasts. In Trading Spouses middle class families—one white, one black—swap husbands and it gets super awkward and weird. We would've been happy to see more Leonard Washington, too.

18. The Wayne Brady Show

Wayne Brady is today the host of The Price Is Right. As incredibly gifted and funny as Brady is, you could say at one time that he was the anti-Chappelle; no sharp edges, no controversy, everything lighthearted. After iconic comedy writer Paul Mooney made Brady a punchline in one episode, the comedian guested on the show and revealed a radically different man under his smiling facade.

17. The World Series of Dice

Chappelle's Show had an entire category of twisted sporting events sketches. The World Series of Dice was great not just for Donnell Rawlings' Ashy Larry, but the return of Leonard Washington. 

16. R. Kelly's "Piss On You"

One of the funniest things about Dave Chappelle singing is he can't sing. Add in his gross but funny rip on singer R. Kelly's disgusting sex scandal and try to not giggle in a kind of queasy way through the whole thing.

15. Knee-High Park

First thing's first: Did Chappelle and his players—including the unmistakable voice of Snoop Dogg—really drop some of these lines in front of kids, or were they intercut through the magic of video editing? Because this very Chappelle's Show riff on a Sesame Street-style show is even funnier if they did.

14. Tyrone Biggums's Classroom Visit

Tyrone was arguably Dave Chappelle's most memorable repeat character. The most honest crackhead ever once tried his hand at promoting drug awareness, and it didn't go well.

13. The Niggar Family

One thing Chappelle's Show could do was find original ways to make everyone laugh and kind of squirm at a socially-conscious subtext. In The Niggar Family, he takes on a Leave it to Beaver-style 50s sitcom with a really awkward title.

12. Fisticuffs

Rap was part of the fabric of the show, and Chappelle proved there was a lot of comedy potential in it. Fisticuffs was his perfect take on early 2000s hip hop, a rapper who could never quite get it going, but damn if he wasn't gonna keep on till he got it right.

11. The Playa Haters' Ball

"The most prestigious verbal abusers on the planet" gathered at one point to single out the greatest hater, and the end result was a master class in shade as well as comedy that never gets old.

10. Roots Outtakes

This parody of outtakes collections using one of the most consequential miniseries in TV history would be higher up the list, but when Chappelle's Show was airing there were probably more viewers who remembered the revered 1970s mini-series.

9. The Racial Draft

Racial Draft is a sketch that might not make it to the screen today—racial awareness, especially issues of identity, are at a different place. They were controversial enough when Chappelle assembled racial minorities to sort various celebrities, but that doesn't make this any less hilarious.

8. Ask a Black Dude

Comedy writer Paul Mooney is over it all, including dumb questions about black people. There's something in his combination of world-weariness and deadpan delivery here that makes us wish Mooney had been on the show more often.  

7. Charlie Murphy's True Hollywood Stories—Rick James

Some might say "habitual line-stepper" Rick James is one of Chappelle's greatest impressions. The real stars of this sketch, though, are Charlie Murphy with his plainspoken storytelling style, and the real Rick James—who Chappelle totally nails.  

6. The Mad Real World

You could argue there was a dark element to a lot of Chappelle's Show sketches, but this may have been one of the darkest. Nerdy white dude Chad is thrown into a house full of very different roommates and struggles to survive.

5. Clayton Bigsby

Bigsby was a blind black man who was in the KKK because, well, he didn't know he was black. That was how Chappelle managed to cut into bigotry with his razor-sharp parody. Even if the whole thing wasn't hilarious, watching Bigsby remove his hood was priceless.

4. Electric Guitar, Drums, or Electric Piano

With John Mayer and Questlove, Dave tested the preferred musical instruments among Latinos and black people. It was the kind of thing pretty much only he could do and get away with it.

3. I Know Black People

 Chappelle was even more creative than usual with I Know Black People. In a classic game show set-up, he questioned a set of average New Yorkers—not actors—about what they really know about their black friends and acquaintances. If you've ever wondered at the true nature of pimping, you'll learn from watching this.   

2. Tyrone Biggums's Crack Intervention

Look, Tyrone shouldn't have been funny. Chappelle took a really sad stereotype and made him one of the most memorable characters on the show. And besides, Tyrone Biggums was part of a long-running saga, a hero's journey in which a man pursues his eternal path to another rock. As the sketch of his intervention makes clear, nothing could ever stand in his way.

1. Charlie Murphy's True Hollywood Stories - Prince

Other lists of great Chappelle's Show sketches never seem to place this one at the top, and that's just wrong. While 20 through 2 are totally negotiable, this is not. It has everything: Charlie Murphy's masterful straight-faced delivery, a truly surprising and funny story (which Prince collaborator Micki Free later confirmed was true) and most of all Dave's absolutely hysterical Prince impression. He doesn't look like the late Purple One, he doesn't sound a thing like him, and somehow he's still perfect.