The Best Episodes of Chappelle's Show

Last Updated: Nov 25, 2018

"Chappelle's Show" takes comedian Dave Chappelle's own personal joke book and brings it to life, with episodes consisting of sketches, man-on-the-street pieces, and pop culture parodies introduced by Dave in a stand-up format in front of a studio audience. Chappelle's unique point-of-view on the world provides a hilarious, defiant and sometimes dangerous look at American culture, including music, movies, television, advertising, current events, and everyday life situations.

True Hollywood Stories - Rick James

#1 - True Hollywood Stories - Rick James

Season 2 - Episode 4

Dave unveils the Love Contract and offers up the True Hollywood Story of actor Charlie Murphy, along with musical guest Ludacris.

star 8.61
415 votes
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The Wayne Brady Show

#2 - The Wayne Brady Show

Season 2 - Episode 12

Dave quits his show at Comedy Central and is promptly replaced by comedian Wayne Brady. Dave returns as crackhead Tyrone Biggums, who appears as a guest on "Fear Factor." Dave also hangs out with Wayne Brady, who proves to be unexpectedly menacing. Also featuring music performer Talib Kweli.

star 8.46
189 votes
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True Hollywood Stories - Prince

#3 - True Hollywood Stories - Prince

Season 2 - Episode 5

Paul Mooney provides answers about the mysteries of life as "Negrodamus." "Charlie Murphy's True Hollywood Story" focuses on Prince, as he takes to the basketball court. Also featuring musical guest Cee-Lo.

star 8.33
318 votes
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Trading Spouses

#4 - Trading Spouses

Season 1 - Episode 12

Dave delves into what would happen if couples attempted "Trading Spouses" and introduces a new family-oriented form of marijuana which contains no THC. Also featuring musical guest Blackstar.

star 8.25
139 votes
Writers: Neal Brennan, Dave Chappelle
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Black White Supremacist

#5 - Black White Supremacist

Season 1 - Episode 1

Dave pokes fun at an annoying Mitsubishi car commercial. Dave appears in a video to show Popcopy copy store employees how to annoy the customers. Dave makes a case for hip-hop's degradation of women, which ruins the legacy of Nat King Cole. Learn how to order your very own home stenographer. Dave plays a blind, angry white supremacist who joins the KKK, but doesn't know he's black.

star 8.19
727 votes
Writers: Dave Chappelle, Neal Brennan
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I Know Black People

#6 - I Know Black People

Season 2 - Episode 8

Dave hosts the game show "I Know Black People" and offers up another look at "When Keeping it Real Goes Wrong." Also featuring musical performer Erykah Badu.

star 8.17
133 votes
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The Niggar Family

#7 - The Niggar Family

Season 2 - Episode 2

Dave looks at what it would be like to have a black version of watermelon-smashing comedian Gallagher. Paul Mooney plays "Negrodamus" and Dave plays Calvin, who gets a job at WacArnolds. Also featuring music performer DMX.

star 8.15
226 votes
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Black Bush

#8 - Black Bush

Season 2 - Episode 13

Dave looks at recent world events and tries to assess the way things would have gone had President Bush been black. Dave takes a look back at the first black person in history to use a white toilet. Dave also examines a moment in the life of Lil Jon when he plays the rapper while talking to the real Lil Jon on the phone. Also featuring a musical performance by Big Boi.

star 8.12
116 votes
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The Racial Draft

#9 - The Racial Draft

Season 2 - Episode 1

Dave runs for office and offers a look at life in slow motion. Dave also plays Samuel L Jackson in a beer commercial, and co-commentates on the first-ever "Racial Draft."

star 8.12
242 votes
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Making Da Band

#10 - Making Da Band

Season 2 - Episode 10

Dave takes a closer look at the P. Diddy-produced reality television show called "Making Da Band" and introduces a new children's show called "Kneehigh Park." Also featuring musical guests Snoop Dogg, and Wyclef and Q-Tip.

star 8.08
139 votes
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If The Internet Were Real

#11 - If The Internet Were Real

Season 2 - Episode 6

Dave examines what the daily life of rapper Lil John might be like and tries to imagine how the internet would look if it was an actual place. Also featuring musical guest Anthony Hamilton.

star 8.08
145 votes
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Inner City Gang Wars

#12 - Inner City Gang Wars

Season 1 - Episode 10

Dave looks at one of the world's greatest wars. He also examines R. Kelly's older videos to point out the future sex crimes that are indicated in the material. Also featuring another segment of "Ask a Black Dude" with Paul Mooney and a musical performance by GZA.

star 8.06
195 votes
Writers: Dave Chappelle, Neal Brennan
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Introducing Tyrone Biggums

#13 - Introducing Tyrone Biggums

Season 1 - Episode 2

Dave plays crack addict Tyrone Biggums, who gives a speech to an elementary school classroom. Also featuring musical guest Mos Def.

star 8.02
462 votes
Writers: Dave Chappelle, Neal Brennan
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Lost Episode 3

#14 - Lost Episode 3

Season 3 - Episode 3

Dave meets the powerful Show Business and offers a look at a bunch of monsters who have seen their share of discrimination.

star 8.01
91 votes
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World Series of Dice

#15 - World Series of Dice

Season 2 - Episode 7

Dave and his friends have a mishap at the drive-thru. A look at the World Series of Dice. Also featuring musical guests Common and Kanye West.

star 8.00
142 votes
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Great Moments in Hookup History

#16 - Great Moments in Hookup History

Season 1 - Episode 5

Dave looks at "Great Moments in Hook-Up History" and is an interview guest on "Inside Chappelle's Show Studio." Paul Mooney hosts a segment of "Ask a Black Dude." Redman offers up his new "Redman Potty Fresh" toilet cleaner in a commercial, and Dave shows a commercial for "Rocka Pads."

star 7.98
275 votes
Writers: Dave Chappelle, Neal Brennan
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Blackzilla

#17 - Blackzilla

Season 1 - Episode 9

Dave invades Japan in the sci-fi-themed "Blackzilla" and stars in his own video game. Dave also offers up a look at the "Player Hater's Ball." Also featuring musical performer The Roots.

star 7.95
207 votes
Writers: Neal Brennan, Dave Chappelle
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Lost Episode 1

#18 - Lost Episode 1

Season 3 - Episode 1

Dave looks to enact vengeance on everyone who has done him wrong in the past after signing a sweet new deal. Meanwhile, people suddenly charge him a lot more money for even the most trivial things that used to cost very little.

star 7.94
192 votes
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The Return of Tyrone Biggums

#19 - The Return of Tyrone Biggums

Season 1 - Episode 8

Dave looks at what really happened behind the scenes of the movies "Ghost" and "Half Baked." Dave goes inside the racism present among Hollywood's animal stars. Dave also returns as crackhead Tyrone Biggums, whose friends stage an intervention and take him to a rehab center. Also featuring a musical performance by Slum Village.

star 7.92
220 votes
Writers: Neal Brennan, Dave Chappelle
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Fisticuffs

#20 - Fisticuffs

Season 1 - Episode 11

Funkmaster Flex hires a rapper, played by Dave, who keeps repeating the same non-lyrical phrases over and over again. Dave visits a kid with cancer, but takes no mercy when he plays the kid at Playstation 2. Dave also buys a camera that has the power to see people's innermost thoughts. Also featuring music performer De La Soul.

star 7.91
151 votes
Writers: Dave Chappelle, Neal Brennan
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The Mad Real World

#21 - The Mad Real World

Season 1 - Episode 6

Dave envisions what "The Real World" would be like with a black cast that includes one super white man. Also featuring musical performer David Broom.

star 7.91
280 votes
Writers: Neal Brennan, Dave Chappelle
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White People Can't Dance

#22 - White People Can't Dance

Season 2 - Episode 3

Dave Chappelle examines the age-old myth about white people's inability to dance. Dave tries out a new sleep aid. The Three Daves: A retrospective look at Dave at age 18, 24 and 30.

star 7.90
178 votes
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Wu-Tang Consulting Firm

#23 - Wu-Tang Consulting Firm

Season 1 - Episode 7

Dave takes a look at a great moment in hook-up history and shows "Real Movies" based on "The Matrix" and a grim look at "Pretty Woman." The Wu Tang Clan advertises their new financial firm, and Paul Mooney offers up another segment of "Ask a Black Dude." A Jedi Scandal is exposed. Also featuring music performer Killer Mike.

star 7.86
217 votes
Writers: Dave Chappelle, Neal Brennan
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Love Those Breasts

#24 - Love Those Breasts

Season 1 - Episode 3

Dave plays an angel who shows a woman, regretful of her large chest, the error of her ways in "It's a Wonderful Chest." A shopping network spoof finds QVC selling very odd and distasteful items. Dave also shares humorous outtakes from the classic miniseries "Roots." Also featuring musical performer Talib Kweli.

star 7.80
364 votes
Writers: Dave Chappelle, Neal Brennan
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Lost Episode 2

#25 - Lost Episode 2

Season 3 - Episode 2

Dave hits the campaign trail as yell-happy presidential candidate Howard Dean and assumes the role of an antagonistic Gary Coleman. He also attempts to elude a crop of persistent racial stereotype pixies.

star 7.77
92 votes
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