The 20 Best 'Chappelle's Show' Sketches Of All time

From Clayton Bigsby to Charlie Murphy's Hollywood stories about Prince and Rick James, these are the 20 best Chappelle's Show sketches.

Through its short two-and-a-half season run, Dave Chappelle'sChappelle's Show was miraculously able to create some of the best sketch comedy to ever appear on television. From its hilarious pilot to its brief yet thoughtful third season, Chappelle's Show became the blueprint for modern sketch comedy.

Setting itself apart from network staples like Saturday Night Live and MadTV with its specifically race-focused humor and dedication to commenting on current black-focused news, Chappelle’s Show's experimental format created a space for shows like Key & Peele and, most recently, The New Negroes. Sixteen years later, Chappelle's comedic voice has already gone down in comedy history.

Let's look back at 20 of the show's best sketches:

20. Pretty White Girls Sings Dave's Thoughts

Chappelle's Show always excelled at creating something funny from the simplest premises. It's one thing to know that your jokes would sound more palatable out of a white woman's mouth. But it's another thing entirely to get a classically trained singer in a gown to share your thoughts in the format of a Rodgers & Hammerstein's musical number. Somehow, Dave standing right next to her laughing at his own jokes made the punchlines hit even harder. But, it's these two lines that make the entire sketch worth it:

Pretty White Woman: (singing) "OJ didn't do it."

[Dave hands her another note card.]

Pretty White Woman: (singing) "On second thought, yeah he did."

19. Samuel Jackson Beer

For a show known for its impressions, it's tough to pick a favorite. But there's something so infectious about a Samuel L. Jackson impression, and Chappelle gets the voice and mouth movements of the man perfectly. This sketch is a great showcase for how Chappelle used facial contortion to become the man he's imitating, despite obvious differences in appearance. Also, it's just funny to watch him scream in Bill Burr's face.

18. Wu-Tang Financial

It's hard to explain why, out of the hip-hop influenced commercial sketches, "Wu-Tang Financial" is the funniest. Many rappers — like JAY-Z — grow into their money and begin to see themselves as financial advisors. The Wu-Tang Clan has never taken themselves quite that seriously, which is probably why their advisory approach feels so honest and relaxed. It's an endearing, simple little sketch.

17. Wrap It Up Box

The "Wrap It Up" box is one of those fake products that couldn't exist in real life because of the endless fights it would cause. It's annoying enough to watch an awards show and see legendary artists get played off right when they start thanking their families. The real-life implications would be so much worse. This sketch is sold entirely by featured player Guillermo Diaz, who brings one of the boxes to his court hearing so he can avoid pedantic lectures after his sentencing.

16. Mooney on Movies

Chappelle's Show always made room for the legendary Paul Mooney. Whether he was answering general questions about blackness or just throwing shade, Paul Mooney was the master of his artform. I think that's why his recurring sketch was always changing — he was the star and it didn't matter what he was talking about. But there was something extra special about Mooney's thoughts on film. "Mooney On Movies" made me want an entire show where he just riffed on whatever was playing that week. Comedy Central should have greenlit that.

15. Home Stenographer

These things could save lives! Dave should have patented this product! Imagine the arguments you could win if there was someone at your house typing up transcripts of all your conversations? Would that lower the divorce rate? The marriage rate? Would they become part of the family? Who is paying for their lodgings? All important questions. But what matters is that you were right, your man lied, and now you can quit couple's therapy and just leave him.

14. Making the Band

This sketch was great at capturing a specific moment in time when we all believed that Diddy cared about helping young artists get big. We all know better now, but Chappelle's Show knew it first. Using actual contestants from the show, "Making the Band" not only perfectly captures the spirit of Diddy's vanity project. It slyly pokes fun at the concept of a very rich man wielding his power over working class people and pretending the power imbalance has educational value. Where is Da Band now? Danity Kane? Day26? A reunion sketch with all of them would be amazing.

13. When Keeping It Real Goes Wrong

These sketches are pretty easy to write off as "respectability politics," and there's no denying that there's a streak of that with them. But there's something really fascinating about the way they illustrate how easy it is for black people to get caught up, simply for expressing momentary anger. When you throw masculinity into the mix it gets even dicier, because black men are often asked to perform anger to prove their "manhood." Still, none of the instances in the sketches really count as microaggressions, so I'm sure Chappelle would argue that the sketches aren't necessarily about taking injustice lying down. It's more generally about keeping yourself in check to protect your life and career. That's an important thing to keep in mind. Also, maybe go to therapy.

12. A Moment in the Life of Lil’ Jon

The best thing about Chappelle's Lil' Jon impression is how loving it is. In every iteration of the sketch, you can tell how much Dave enjoys and admires the rapper. The sketches hinge on this image of Lil' Jon as an overly positive man with poetic inner depths. Who else would think to portray the rapper behind Crunk Juice as an early incarnation of Bojack Horseman's Mr. Peanutbutter but Dave Chappelle? Think about it: he's an almost ageless, endlessly cheerful grown man with the energy of a teenager and a hint of existential angst. The thinkpieces write themselves.

11. Charlie Murphy’s True Hollywood Stories: Prince

Chappelle is lovable as Prince, playing him as a cool black Jack Sparrow. But the real star of the sketch is Charlie Murphy. The late, great Murphy was the breakout star of Chappelle's Show, and rightly so. The way he managed to use his masculinity as a tool for comedy, with an almost lovable rage akin to The Wire's Michael K. Williams. There's something sweet about him sharing a story where Prince, a gender-defying black icon, beats him at basketball and then makes him a pancake dinner. Comedy doesn't need to have a message, but I think this particular sketch has a nice one about how masculinity can take different forms.

10. Racial Draft

The genius of "Racial Draft" lies in its simplicity. It showcases what Chappelle's Show did best: taking everyday barbershop talk and heightening it into elaborate comedy. Everyone partakes in the game of trying to figure out which race a celebrity really belongs to. The sketch plays on the universality of the conversation while also highlighting how complicated racial heritage can be to pin down. But above all, making Colin Powell "officially white" is hilarious.

9. Tyrone Biggums Classroom Visit

Out of all the appearances of Tyrone Biggums, none hit quite as hard as this one. Here we have a very Reagan-esque concept of a drug addict coming to speak to kids and scare them into not doing drugs. As any child of the '80s or '90s will tell you, these visits usually led us to seek out drugs instead of stay away from them. Having Tyrone address the class with such passion for drugs plays on that fact, highlighting how harmful those visits were, as well as the DARE program in general. Tyrone's comedic appeal works best here, and his impact would have probably been much stronger if he had never become a recurring character.

8. The Mad Real World

This sketch is the miraculous marriage of a funny premise and even funnier execution. It not only skewers reality shows, it also critiques the way producers purposely put people of color into hostile situations for the sake of manufactured drama and ratings. The same could be said of all reality show situations. But there is something especially insidious about putting a normal, well-adjusted black person in a house with a bunch of white people who tend to be racist, erratic, and belligerent. Even now, during a television age saturated with a variety of reality shows, it's still cathartic to watch an average white guy being the minority in an all-black house. Christian Finnegan is perfect as the ultimate white guy sad sack.

7. I Know Black People

This is one of those sketches that is easily forgotten among the more heightened material, but it's a gem. The key to it is how the game reveals how little non-black people seem to know about a culture that everyone is quick to size up. Easy questions about Good Times and the term "badonkadonk" are met with head-scratching and confusion. The inclusion of a white female cop among the contestants is especially interesting, considering the last 5 years. 

Best Exchange

Dave: "How will black people rise up and overcome?"

White Female Cop: "Get out and vote."

[buzzer sounds]

Dave: "That's incorrect!"

6. First Black Man to Use a White Toilet

The funniest thing about this sketch is that it feels accurate. Beneath the numerous poop jokes is a nightmarish situation: what was it like the first couple years that bathrooms were integrated? Considering the hostility toward gender-neutral bathrooms in the present and the violence that trans and gender non-conforming people have faced as a result, it’s easy to accept that white people wouldn't share their bathrooms without a fight. "First Black Man to Use a White Toilet" uses juvenile potty humor to share a story that's probably not that far from the truth.

5. The Wayne Brady Show

Every couple of episodes, Chappelle would make a crack or two about the possibility of being canceled. It's interesting then that the episode before he leaves the show for good is about the possibility of him losing it to the more classically charismatic Wayne Brady. Wayne Brady is hilarious in the episode and it serves as the beginning of his rebranding, playing on the image we expect from him to give us something new and even funnier. But beyond that, it's Chappelle's anxiety that really holds the sketch together. "The Wayne Brady Show" reminds us that Chappelle is just a man, and gave us a bit of a hint that he was starting to get tired of being perceived as just a provocateur. It's an episode-long sketch that's both hilarious and heartfelt.

4. Charlie Murphy's True Hollywood Stories: Rick James

What can be said about a classic? All you have to say is "I'm Rick James, bitch!" and suddenly we're in a time machine going back to 2004. This sketch did more for Rick James than a Hollywood biopic ever could. Chappelle is having a blast playing the legendary artist. He's like a coked-up Bugs Bunny, and Charlie Murphy is Elmer Fudd trying not to lose his mind. The added bonus of Rick James himself commenting on the story only heightens the comedy.

3. The Playa Hater’s Ball

Everyone brings their A-game to this sketch, from recurring favorites Charlie Murphy and Donnell Rawlings to Ice-T and the late, great Patrice O'Neal. This is a concept straight out of blaxploitation, with Willie Dynamite as a clear influence. While the "PIMP (Remix)" video of the same year brought back the classic understanding of the pimp, "Playa Hater's Ball" takes that history and makes something new. Silky Johnson is one of Chappelle's best characters, and every line out of his mouth is quotable.

2. The Niggar Family

This is probably the first and last time I laughed at white people using the word "nigger" and that in itself is a miraculous triumph. This is the sketch where Chappelle's Show lives up to its reputation of being "dangerous." But even more notable than the overt provocation in the premise, is the period detail that suggests a world where Leave It To Beaver had racial commentary. Chappelle is hilarious all on his own as a black milkman who takes a perverse joy in calling the white family he works for, by the same word that is used to degrade him on a daily basis. This sketch honestly shouldn't work, but it really does.

1. Frontline: Clayton Bigsby

It feels odd to say that the best sketch in the entire series was in the very first episode. But truthfully nothing on Chappelle's Show ever got close to the brilliance of the Clayton Bigsby story. Premiering over a decade before Spike Lee's Oscar-winning film BlackKklansman, "Frontline: Clayton Bigsby" skewered the absurdity of white supremacist ideology by presenting us with the possibility of a blind white supremacist who managed to hate black people while secretly being one. I can't imagine that there will ever be a better sketch about racism in America.

__

This story was originally published in 2019.

Jourdain Searles is a writer, comedian, and podcaster who hails from Georgia and resides in Queens. She has written for Bitch Media, Thrillist, The Ringer, and MTV News. As a comic, she has performed stand-up in venues all over New York City, including Union Hall, The People Improv's Theater, UCB East, and The Creek and the Cave. She can be found on Twitter.