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The Best Episodes of Chappelle's Show

Every episode of Chappelle's Show ranked from best to worst. Let's dive into the Best Episodes of Chappelle's Show!

Binge this in 10h 16m•Peaking at 9.4/10

Dave Chappelle's singular point of view is unleashed through a combination of laidback stand-up and street-smart sketches.

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Episode Rankings

  1. #1 Fan Favorite
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    Chappelle's Show Season 2 Episode 4 - True Hollywood Stories - Rick James
    9.4/10(1139 votes)

    S2:E4

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

    Director:Unknown
    Writer:Unknown

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  2. Chappelle's Show Season 2 Episode 12 - The Wayne Brady Show
    9.0/10(679 votes)

    S2:E12

    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.

    Director:Unknown
    Writer:Unknown

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  3. Chappelle's Show Season 2 Episode 5 - True Hollywood Stories - Prince
    8.8/10(675 votes)

    S2:E5

    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.

    Director:Unknown
    Writer:Unknown

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  4. Chappelle's Show Season 1 Episode 1 - Black White Supremacist
    8.6/10(1173 votes)

    S1:E1

    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.

    Director:Unknown
    Writer:Unknown

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  5. Chappelle's Show Season 2 Episode 1 - The Racial Draft
    8.6/10(642 votes)

    S2:E1

    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."

    Director:Unknown
    Writer:Unknown

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  6. Chappelle's Show Season 2 Episode 2 - The Niggar Family
    8.5/10(605 votes)

    S2:E2

    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.

    Director:Unknown
    Writer:Unknown

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    The 20 WORST Episodes of Chappelle's Show

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  7. Chappelle's Show Season 2 Episode 8 - I Know Black People
    8.1/10(511 votes)

    S2:E8

    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.

    Director:Unknown
    Writer:Unknown

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  8. Chappelle's Show Season 2 Episode 9 - Oprah's Baby Daddy
    8.1/10(478 votes)

    S2:E9

    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.

    Director:Unknown
    Writer:Unknown

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  9. Chappelle's Show Season 2 Episode 10 - Making Da Band
    8.1/10(512 votes)

    S2:E10

    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.

    Director:Unknown
    Writer:Unknown

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  10. Chappelle's Show Season 2 Episode 13 - Black Bush
    8.1/10(495 votes)

    S2:E13

    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.

    Director:Unknown
    Writer:Unknown

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  11. Chappelle's Show Season 1 Episode 6 - The Mad Real World
    8.0/10(708 votes)

    S1:E6

    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.

    Director:Unknown
    Writer:Unknown

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  12. Chappelle's Show Season 1 Episode 10 - Inner City Gang Wars
    8.0/10(561 votes)

    S1:E10

    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.

    Director:Unknown
    Writer:Unknown

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  13. Chappelle's Show Season 2 Episode 3 - White People Can't Dance
    8.0/10(541 votes)

    S2:E3

    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.

    Director:Unknown
    Writer:Unknown

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  14. Chappelle's Show Season 1 Episode 2 - Introducing Tyrone Biggums
    7.9/10(818 votes)

    S1:E2

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

    Director:Unknown
    Writer:Unknown

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  15. Chappelle's Show Season 1 Episode 9 - Blackzilla
    7.9/10(596 votes)

    S1:E9

    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.

    Director:Unknown
    Writer:Unknown

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  16. Chappelle's Show Season 2 Episode 6 - If The Internet Were Real
    7.9/10(478 votes)

    S2:E6

    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.

    Director:Unknown
    Writer:Unknown

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  17. Chappelle's Show Season 2 Episode 7 - World Series of Dice
    7.9/10(516 votes)

    S2:E7

    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.

    Director:Unknown
    Writer:Unknown

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  18. Chappelle's Show Season 1 Episode 4 - Slavery Reparations
    7.8/10(694 votes)

    S1:E4

    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.

    Director:Unknown
    Writer:Unknown

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  19. Chappelle's Show Season 1 Episode 5 - Great Moments in Hookup History
    7.7/10(663 votes)

    S1:E5

    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."

    Director:Unknown
    Writer:Unknown

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  20. Chappelle's Show Season 1 Episode 7 - Wu-Tang Consulting Firm
    7.7/10(607 votes)

    S1:E7

    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.

    Director:Unknown
    Writer:Unknown

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  21. Chappelle's Show Season 1 Episode 8 - The Return of Tyrone Biggums
    7.7/10(569 votes)

    S1:E8

    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.

    Director:Unknown
    Writer:Unknown

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  22. Chappelle's Show Season 1 Episode 12 - Trading Spouses
    7.7/10(529 votes)

    S1:E12

    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.

    Director:Rusty Cundieff
    Writers:Nick Kroll, Neal Brennan, Dave Chappelle, Norman Lear

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  23. Chappelle's Show Season 3 Episode 1 - Lost Episode 1
    7.7/10(379 votes)

    S3:E1

    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.

    Director:Unknown
    Writer:Unknown

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  24. Chappelle's Show Season 1 Episode 11 - Fisticuffs
    7.6/10(536 votes)

    S1:E11

    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.

    Director:Unknown
    Writer:Unknown

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  25. Chappelle's Show Season 1 Episode 3 - Love Those Breasts
    7.5/10(714 votes)

    S1:E3

    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.

    Director:Unknown
    Writer:Unknown

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Best Episodes Summary

"True Hollywood Stories - Rick James" is the best rated episode of "Chappelle's Show". It scored 9.4/10 based on 1139 votes. Directed by Unknown and written by Unknown, it aired on 2/11/2004. This episode scored 0.4 points higher than the second highest rated, "The Wayne Brady Show".