The BEST episodes of Chappelle's Show

Every episode of Chappelle's Show ever, ranked from best to worst by thousands of votes from fans of the show. The best episodes of Chappelle's Show!

"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.

Last Updated: 9/30/2023Network: Comedy CentralStatus: Ended
True Hollywood Stories - Rick James
706 votes

#1 - True Hollywood Stories - Rick James

Season 2 - Episode 4 - Aired 2/11/2004

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

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Trading Spouses
414 votes

#2 - Trading Spouses

Season 1 - Episode 12 - Aired 4/9/2003

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.

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The Wayne Brady Show
394 votes

#3 - The Wayne Brady Show

Season 2 - Episode 12 - Aired 4/7/2004

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.

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The Racial Draft
552 votes

#4 - The Racial Draft

Season 2 - Episode 1 - Aired 1/21/2004

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."

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The Niggar Family
434 votes

#5 - The Niggar Family

Season 2 - Episode 2 - Aired 1/28/2004

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.

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Introducing Tyrone Biggums
824 votes

#6 - Introducing Tyrone Biggums

Season 1 - Episode 2 - Aired 1/29/2003

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

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392 votes

#7 - Fisticuffs

Season 1 - Episode 11 - Aired 4/2/2003

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.

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Inner City Gang Wars
462 votes

#8 - Inner City Gang Wars

Season 1 - Episode 10 - Aired 3/26/2003

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.

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Black White Supremacist
1149 votes

#9 - Black White Supremacist

Season 1 - Episode 1 - Aired 1/22/2003

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.

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The Mad Real World
550 votes

#10 - The Mad Real World

Season 1 - Episode 6 - Aired 2/26/2003

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.

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True Hollywood Stories - Prince
570 votes

#11 - True Hollywood Stories - Prince

Season 2 - Episode 5 - Aired 2/18/2004

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.

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The Return of Tyrone Biggums
482 votes

#12 - The Return of Tyrone Biggums

Season 1 - Episode 8 - Aired 3/12/2003

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.

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Slavery Reparations
655 votes

#13 - Slavery Reparations

Season 1 - Episode 4 - Aired 2/12/2003

Dave gives out awards to women with great "New York Boobs" and assesses the problems that would result from offering slavery reparations. Also featuring musical guest Busta Rhymes.

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I Know Black People
264 votes

#14 - I Know Black People

Season 2 - Episode 8 - Aired 3/10/2004

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.

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Wu-Tang Consulting Firm
544 votes

#15 - Wu-Tang Consulting Firm

Season 1 - Episode 7 - Aired 3/5/2003

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.

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Making Da Band
258 votes

#16 - Making Da Band

Season 2 - Episode 10 - Aired 3/25/2004

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.

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World Series of Dice
298 votes

#17 - World Series of Dice

Season 2 - Episode 7 - Aired 3/3/2004

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.

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Black Bush
209 votes

#18 - Black Bush

Season 2 - Episode 13 - Aired 4/14/2004

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.

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Great Moments in Hookup History
567 votes

#19 - Great Moments in Hookup History

Season 1 - Episode 5 - Aired 2/19/2003

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."

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If The Internet Were Real
317 votes

#20 - If The Internet Were Real

Season 2 - Episode 6 - Aired 2/25/2004

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.

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466 votes

#21 - Blackzilla

Season 1 - Episode 9 - Aired 3/19/2003

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.

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Lost Episode 3
181 votes

#22 - Lost Episode 3

Season 3 - Episode 3 - Aired 7/23/2006

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

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White People Can't Dance
362 votes

#23 - White People Can't Dance

Season 2 - Episode 3 - Aired 2/4/2004

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.

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Greatest Misses
209 votes

#24 - Greatest Misses

Season 2 - Episode 11 - Aired 3/31/2004

Dave introduces skits that were too crazy to make the cut, including footage of a trip to the Nelson Mandela bootcamp for teenagers. Dave also imagines what it would be like if the whole world was gay. Also featuring musical guests Kanye West and Mos Def.

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Oprah's Baby Daddy
279 votes

#25 - Oprah's Baby Daddy

Season 2 - Episode 9 - Aired 3/24/2004

Dave thinks Oprah is pregant with his child. Dave also goes into his experience as a member of the O.J. Simpson trial jury. Also featuring musical guest Wyclef.

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