When we looked back at the best sketch comedy shows of the last 30 years a few months ago we said Chappelle’s Show often reached “a rarefied space with material that was surprising, unforgettable, and occasionally even profound.” And then we ranked it number 1. After a rewatch made possible by the show’s arrival on Netflix (and HBO Max), it’s easy to double down on that praise, particularly when you consider not just the more memorable sketches but also the truly inspired doubles and triples that helped to make each episode ripe for revisitation. A quick revisitation, since there are only 28 of them.
To inspire that ride, we decided to look back at the 15 best sketches from the show’s run, which is, of course, a highly subjective thing to do. I promise you, you will question my sanity and ability to do this job after reading this list (more than the normal amount, even). Especially since I have a predilection for some more obscure sketches that aren’t likely to front other such lists. But isn’t that part of the point? Sparking conversation and passionate defense of your favorites So, this is my attempt, read it, hopefully enjoy some of it, and then fire back with your own.
15. What Makes White People Dance – S2E3
Under the guise of social anthropology, Chappelle and his pal John Mayer infiltrate a board room, a restaurant, and a barbershop to prove the theory that the electric guitar entrances cause white people to dance. It is a silly, random bit that hits a high point when Questlove pops up to expand on the theory, but the best thing connected to this might be Chappelle, Mayer, and Questlove’s cover of the Diff’rent Strokes theme song at the end of the episode.
14. AND-1 Mixtape – S1E12
The above clip is only a small part. You can check out the full clip of Chappelle mocking baseball, tennis, and bowling’s inability to showcase showoffs to the level of streetball here. This predates the slight uptick in expressiveness and personality in baseball, so I’d actually kill to see an AND-1 level video of bat flips and dugout dances in 2020. Nevertheless, this still lands, especially the visual of Chappelle stunting while bowling.
13. Make A Wish Kid – S1E11
Chappelle goes to visit a sick kid and plays a video game with him to ease his pain. Until Chappelle’s competitive fire gets the best of him. Goddamn does this get dark. If you’re a fan of fucked up comedy, this probably ranks higher on the list for you than for most other folks.
12. Roots Outakes – S1E3
The laughs come from the absurdity of some executive being oblivious enough to try and mine the reverence felt for Roots by adding bloopers and goofs to a special edition DVD, but this also feels like a comment about the entertainment industry’s eagerness to profit off Black trauma.
11. Tyrone Biggums’ Classroom Visit – S1E2
Plenty of ways to celebrate one of Chappelle’s Show’s most enduring characters — the intervention sketch, the Fear Factor sketch — but I’ll go with the first impression for the initial shock value of seeing Tyrone taint a classroom full of children with a few anecdotes and one trash can poop.
10. Dave Gets Oprah Pregnant – S2E8
It’s okay to have dreams, folks. Dave’s is to claim a share of Oprah’s seemingly endless treasure by putting a baby inside of her and we are here for it as Chappelle lives life to the fullest, painting nudes, getting extended massages, and rocking crowns while boxing out Oprah’s previous boyfriend and providing the bare minimum of emotional support to Oprah.
9. Kneehigh Park – S2E10
Another dark sketch, this time using the look and feel of a kid’s puppet show to talk about heroin, venereal diseases, and introduce the world to a trash can man who has the anthemic “I Said Fuck It” song about giving up lodged firmly in his heart. And then Snoop Dogg and Tyronne Biggums stop by. And that’s to say nothing of the large infected puppet penis that makes an appearance. That is until now. Infected puppet penis.
8. Home Stenographer – S1E1
Chappelle’s Show had a flair for taking tropes and expanding them until the material feels as fresh as it does relatable and this is an example. Because you know if you’ve been in a couple-fight that you’ve been misquoted or misunderstood and cracked the joke about having a stenographer or recording of what you said.
7. Wrap It Up! – S1E2
Like Home Stenographer this is a pretty basic joke made better by the execution as Chappelle takes the idea of playing someone off the stage at the Oscars and applies it to ineffective screwing and other social situations where you want people to just shut up and be done with it. Like me with this article.
6. The Player Haters Ball – S1E9
The original Player Haters Ball is packed with an amazing collection of characters and some of the best work on the show from Donnell Rawlings and the dearly departed Charlie Murphy (as well as Ice T and the late Patrice O’Neal) as they all trade insults and hate with Chappelle’s Silky Johnston. It’s a classic. I couldn’t possibly omit it, but I actually favor the spectacle that is The Player Hater’s Science Fair, where the player haters time travel to become The Time Haters. It’s a completely bonkers idea built atop the foundation of these characters and something too good to keep in a drawer, which is why it’s a part of Chappelle Show’s episode (S2E11) focused on supposed misses and sketches that had failed to make it to air.
5. PopCopy – S1E1
“Why treat the customer this way? Why? Cuz fuck em, that’s why.”
Yes, retail workers can be assholes, but I was working the customer service desk of a Kmart when this sketch first dropped so you can imagine how close to my heart I kept it and how I was maybe missing the point and rooting for the wrong side. Michael Rappaport lying to a customer to get rid of them and then deciding that he’s had enough and needs to just walk away so he can take a shit? I felt that. Customers ask stupid questions stupidly and so much of the retail existence is just trying to get past dealing with them so you can hang out with your friends. Retail workers were heroes long before they had to deal with regular customer nonsense and COVID exposure at the same time.
4. Charlie Murphy’s True Hollywood Stories: Prince – S2E5
3. Charlie Murphy’s True Hollywood Stories: Rick James – S2E4
This is essentially a tie. So many elements from Chappelle’s Show have stuck around, but “cocaine is a hell of a drug,” pickup basketball and pancakes with Prince, and “I’m Rick James bitch!” may be the most enduring and referenced. Leaning on Murphy’s amazing life of experiences running with his famous brother Eddie was a genius move that showcased Murphy and unlocked Chappelle’s amazing Rick James and Prince impressions. But nothing compares to James, himself, refuting (and then instantly confirming) elements from Murphy’s tale. Print the legend.
2. Mad Real World – S1E6
Longform sketch comedy at its best and a bit that benefits so much from really perfect and intricate set design and just the density of the scene. There’s so much comedy packed into these 10 or so minutes. And everyone gets a turn, specifically Donnell Rawlings, Charlie Murphy, and comedian Christian Finnegan, who steals the whole thing as a plucky Real World roommate who gets run through a gauntlet of psychological and physical bullying and torture, losing his girlfriend and almost his mind. This narrowly misses being the best Chappelle’s Show sketch but it’s my personal favorite.
1. Clayton Bigsby, The World’s Only Black White Supremacist – S1E1
The plot is summed up completely by the title and the biggest laugh probably comes in the first 90 seconds with Chappelle’s reveal as Bigsby, an aged, blind, hatemonger who thinks he’s white. But the genius is in the slow play execution and commitment of Chappelle and the late William Bogert, who plays the straight-laced Frontline reporter. It’s a nine-minute sketch that builds the world around Bigsby, leading to a fuller payoff at the end when all is revealed… including what might be the second greatest exploding head in entertainment history next to the dude in Scanners.
I don’t just remember the sketch, I remember seeing it for the first time, how hard it hit, and how clearly it announced the intentions of the show. There are so many iconic moments on this list but this is the one that sort of paved the way for everything that followed so how do you not put it at number one? That’s a rhetorical question, but I await your replies.
Honorable Mention:
These sketches fell just shy of the top 15 but we had to mention them.
Trading Spouses — Cultures collide as Chappelle’s Show explores weird wife swap reality shows.
WacArnolds — An upbeat and driven fast-food worker’s life turns into a slow-rolling trainwreck.
The Wayne Brady Show — Wayne Brady’s squeaky clean image does all the heavy lifting while taking Chappelle through a nightmare glimpse into his secret life as a lawless gun-toting pimp.
Mos Def Musical Performance — Not a comedy sketch, just an ultracool moment with Yasiin Bey (aka Mos Def) rapping “Close Edge” in the passenger seat while Chappelle drives down a New York street. I hope Chappelle is getting some of James Corden’s Carpool Karaoke money.
Black Bush — Chappelle runs through some of the lowlights of the Bush presidency (remember this show ran from 2004-2006) while imagining how his moves would have been executed and perceived had he been Black.