Top 20 Chappelle's Show Sketches Of All Time

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Top 20 Chappelle's Show Sketches Of All Time

VOICE OVER: Callum Janes WRITTEN BY: George Pacheco
"Chapelle's Show" has managed to stay in the pop culture conversation for so many years thanks to great sketches like these. For this list, we'll be ranking the funniest, most enduring or outrageous shorts from the Comedy Central series. Our countdown includes What Makes White People Dance, the Wrap It Up box, "Trading Spouses," the Playa Haters' Ball, and more!
Transcript
Script written by George Pacheco

"Chapelle's Show" has managed to stay in the pop culture conversation for so many years thanks to great sketches like these. For this list, we’ll be ranking the funniest, most enduring or outrageous shorts from the Comedy Central series. Our countdown includes What Makes White People Dance, the Wrap It Up box, "Trading Spouses," the Playa Haters' Ball, and more! What’s your favorite? Let us know in the comments!

#20: “Mad Real World”


Since we already know what happens when people stop being polite and start being real, we loved seeing this take on a familiar premise. The “Mad Real World '' instantly calls out the lack of diversity that plagues many reality TV shows. Instead of having one or two minority cast members, a Caucasian man is brought into a predominately African-American reality show cast. This opens up the door for sharp and relevant racial commentary. At the same time, this sketch is an excellent parody of the reality tv genre as a whole. While a few jokes definitely might cause you to cringe more than laugh, it overall is a great summary of what’s wrong with reality tv.

#19: “Making the Band”


It didn’t take long for Chappelle to put another MTV reality show in his crosshairs. In this sketch, the comedian dresses up as Diddy and attempts to cultivate new and emerging artists. He starts his sketch by making fun of an infamous moment from MTV’s “Making the Band”. On the original show, Diddy once made contestants walk across a bridge to get him cheesecake. Chappelle’s version of the artist sends his music hopefuls to extremely far locations for random fetch quests. In between his ridiculous requests, there’s a hilarious running gag where he’s too reliant on his security and he parodies “Making the Band’s” most outrageous moments. Even if you’ve never watched Diddy’s original show, you’ll find yourself laughing at this silly parody.

#18: What Makes White People Dance


Dave enlisted the guitar playing talents of John Mayer and got Questlove on the drums for this sketch. Chappelle teams up with these musicians so he can prove society’s beliefs that white people can’t dance are untrue. He shows that a jam band electric guitar puts office workers into an immediate and mellow trance. As soon as Mayer plays a fight riff in a restaurant, all the listeners start a mosh pit. However, the guitar is completely ineffective in a barbershop full of African-American and Hispanic customers. Chappelle ultimately uses other instruments to get everyone in the shop moving. Underneath the jokes about common stereotypes, the comedian is sure to include a message that everyone should feel free to dance.

#17: “World Series of Dice”


In the “World Series of Dice” sketch, a group of eccentric characters are assembled to play an intense high-profile televised sporting event. Chappelle manages to bring in both Eddie Griffin and Bill Burr into this silly sketch. Since the set has intentionally low production value, it’s hilarious to see two guys in full suits provide live commentary. The game is also interrupted by angry partners and a group of thieves. If enough people expressed interest, we’d love to see the World Series of Dice on ESPN one of these days.

#16: Kneehigh Park Sketches


Not even “Sesame Street” was off limits for this acclaimed show. In the“Kneehigh Park” series, innocent looking puppets teach very adult lessons to a young audience nearby. One clip provides an extremely edgy take on Oscar the Grouch. In another segment, a puppet lets his captive audience know all about his adult diseases. And there's a song number that explains the danger of addictive behavior. Each sketch can go from jaw-dropping to gross in just a drop of a hat. But there is one common thread between all of them. None of them should be shown to young audiences.

#15: “I Know Black People” Sketches


The “I Know Black People” sketch had Chapelle hosting a game show that takes a cross section of people and asks them very questions about current African-American culture. People have to know everything from vocabulary to popular tv shows to get all the answers correct. It’s definitely funny to hear contestants from different walks of life answer each of these questions. But it’s also hilarious to see how Chappelle responds to each of their responses. This series of sketches didn’t need a lot of flashy effects or funny costumes. The sharp and witty writing was enough to make them memorable.

#14: The Playa Haters’ Ball


You’d be forgiven for assuming that the “Playa Haters’ Ball” sketch, or its sequel, “Time Haters”, was an original idea from Dave Chappelle and crew. But it turns out the comedian was riffing on a real event. While the actual “Players’ Ball” has been linked to some serious events, Chappelle’s meeting is a decidedly lighter affair. His version is complete with a lot of ridiculous superlative awards and outlandish personalities. The colorful costumes and even more colorful language go hand-in-hand with a bunch of creative and unforgettable names. Featuring a tense awards ceremony and a funny Ice T cameo, this sketch is considered a classic by many fans.

#13: “Lil' Jon At The Airport”


Sometimes a simple concept can provide a ton of great humor. Chappelle knew that less was more when he starred in this sketch. Since Lil’ Jon was known for shouting out a few words in various songs, the comedian exaggerates that and mostly limits the artist’s vocabulary to three words. The fake Lil Jon navigates a complicated airport conversation while screaming out “Yeah”, “Okay” and “What?” over and over again. Chappelle manages to keep the joke fresh with an enthusiastic and committed performance. And as an added bonus, he completely drops the premise at one point and gives Lil’ Jon more lines. This character was so iconic that he was brought back to a fantastic “SNL” skit years later.

#12: Dave Gets Oprah Pregnant


We all dream about winning the lottery and potentially quitting our jobs. However, most probably don’t imagine getting rich the way Chappelle does. In the sketch, the comedian learns that he and Oprah Winfrey are having a baby. He plans to have her use her fortune to fully support him. Chappelle has tons of fun saying goodbye to his work life and colleagues while also subtly hinting at issues he has with the way he’s marketed. He proceeds to blow Oprah’s money like it’s no tomorrow, acts out to basically everyone and takes up a bunch of new hobbies. Unfortunately, his dream turns into a nightmare when it's revealed that he is not the father. It’s a great button for a bizarrely funny premise.

#11: Black Bush


This politically themed sketch had Chappelle become president“Black Bush”. He addresses each problem America was facing at the time with hilariously blunt speeches and actions. Throughout the sketch, Chapelle also meets up with African-American versions of other political figures. This comedic presidential stint gives him a lot of room to speak out against real life issues and political scandals. He also cleverly uses rhetoric from the Bush administration to poke fun at the real commander-and-chief. Chappelle perfectly blended political comedy and hilarious writing for this presidential parody.

#10: The Wrap It Up Box


“As seen on T.V.” product commercials can be funny enough on their own. So, it’s only natural that a Chappelle parody would be comedy gold. The “Wrap It Up Box'' was perhaps the best example of an original item the writing staff came up with. This imaginary item bluntly tells someone that it’s time to finish whatever they're doing. Whether a person’s continuing a dull conversation or talking too much in court, the “Wrap It Up” box lets them know their time is up. Honestly, we’d love to use this box to get out of boring situations in our real lives. Are we sure these aren’t actually for sale?

#9: Wu-Tang Financial


While “Chappelle’s Show” featured a number of high-profile musical guests and stars, bringing the Wu-Tang Clan in for this sketch was truly lightning-in-a-bottle. The “Wu-Tang Financial” group provides a variety of financial services, from investment advice to bond diversification. The way the group mostly plays this sketch straight is what really drives home the absurdity of the situation. Seeing the RZA and GZA selling Wu-Tang Financial as a place for the whole family is definitely an unexpected turn for these musical legends. But we’d still completely trust them with our cash.

#8: “Trading Spouses”


When two families trade dads for a week, men from different backgrounds learn what it's like to walk in another person's shoes.While this describes the program “Trading Spouses” to a tee, it also summarizes a sketch Chappelle starred in before that Fox reality show aired its first episode. The comedian uses the premise to give us some truly bad parents and plenty of awkward interactions. Along the way, it expertly parodies the format and obvious pitbulls of the “Trading Spouses” setup. Every character gets at an arc and at least one laugh-out-loud moment. It’s by far one of the most accurate and funny reality show parodies out there.

#7: Tyrone Biggums Drinks Red Balls


We don’t know about you guys, but we’re pretty sure we’d remember if energy drinks gave us this much power. The “Red Balls” parody was just one hilarious sketch starring the lovable-but-troubled Tyrone Biggums. This drink has given him so much energy that he seems to gain extraordinary hearing, vision and strength. The visual of Tyrone lifting a bus while the “Six Million Dollar Man” theme plays just leaves us rolling every single time. The sketch’s outrageous physical comedy and the way it makes fun of superhero tropes turned it into a fantastic ad. After watching Tyrone star in that commercial, we’re glad he didn’t drink red balls before his class visit.

#6: Frontline: Clayton Bigsby


This boundary pushing sketch is still as shocking and relevant then as it was today. The premise features a reporter meeting the author behind books that negatively impact African-Americans. When the news anchor arrives at a secluded location, he discovers a shocking truth. The writer is an African-American man who’s been unable to see his whole life and was raised as a white person. Not only does the sketch call out the ridiculous beliefs that many hateful groups have, but it also shows how the place a person is raised can negatively shape their entire life. The intense language and imagery of this sketch can be jaw dropping at times. But the layered messages about hate and self-loathing make it an unforgettable dark comedy.

#5: The Wayne Brady Show


We don’t think anyone was expecting a darkly hilarious sketch starring Wayne Brady. This comedian has a reputation for being a pretty wholesome guy. However, this sketch presents him as a violent loose cannon. Dave Chappelle can only watch in horror as Brady drives around for a night with Dave in the passenger seat. Their journey is full of tense moments and insanely quotable lines. And Chpapelle really makes us believe that he’s terrified of Brady. Although this premise may seem underwhelming on paper, the hilarious end results speak for themselves.

#4: A Televised Draft


Chappelle and Bill Burr team up here for a unique kind of draft. In the sketch, representatives from various racial and religious groups get the chance to bring new faces into their cultures. Celebrities like Tiger Woods, Lenny Kravitz and the Wu-Tang Clan are all free agents open to embrace new identities. The sketch fully addresses and parodies a ton of stereotypes society places on different groups. At the same time, the show uses this outlandish setup to make a smart commentary on how people can struggle for acceptance in the culture they were born into. Throughout the draft, Chappelle and Burr’s heavy language and funny observations only further highlight the issues about how different groups are perceived.

#3: Charlie Murphy’s True Hollywood Stories: Prince


We couldn’t do a list of the best sketches without including one of the most iconic bits of comedy from the entire run of “Chappelle’s Show.” Chappelle impersonates Prince on this installment of “Charlie Murphy’s True Hollywood Stories”. The comedian makes the singer into an extremely eccentric celebrity that is constantly trying to stave off boredom. After a few funny interactions, Prince and his crew challenge Murphy and his friends to a basketball game. The singer’s team manages to absolutely dominate their foes with ease. What makes this sketch even funnier was the fact that Eddie Murphy insists that this game actually happened. The late, great Prince could really ball.

#2: Pop Copy


We’ve all suffered through the experience of having to watch video after boring training video whenever we start at a new job. This is a fact that the writers behind “Pop Copy” knew all too well as they parodied this common workplace annoyance. Instead of promoting good practices, the sketch openly shows that employees will behave badly to each other. It also encourages “Pop Copy” trainees to mistreat customers and speak their mind. Not only is this video hilarious, but it also serves as wish fulfillment to anyone who's ever worked in retail. We just wouldn’t recommend ever taking any of Pop Copy’s tips to your own job.

#1: Charlie Murphy’s True Hollywood Stories: Rick James


Certain comedic moments make such an impact that you can remember where you were when they occurred. Every “Chappelle’s Show” fan can clearly remember the first time they saw the Rick James sketch from “Charlie Murphy’s True Hollywood Stories.” Once again, Chappelle gives an absurd and amazing take on a famous singer. Every single thing he says becomes an instantly quotable line. And as Chappelle’s portrayal of the singer gets more and more zany, the real Rick James cuts in to provide commentary and give his perspective on the story. This sketch contains some of the best writing, unexpected twists and physical comedy you’ll find on the show. If you could only show a person one “Chappelle’s Show” sketch, make sure that it’s this.
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