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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(1142 votes)

    #1 - True Hollywood Stories - Rick James

    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(686 votes)

    #2 - The Wayne Brady Show

    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(677 votes)

    #3 - True Hollywood Stories - Prince

    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(1150 votes)

    #4 - Black White Supremacist

    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(648 votes)

    #5 - The Racial Draft

    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
    8.4/10(611 votes)

    #6 - The Niggar Family

    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(516 votes)

    #7 - I Know Black People

    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(484 votes)

    #8 - Oprah's Baby Daddy

    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(525 votes)

    #9 - Making Da Band

    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(504 votes)

    #10 - Black Bush

    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(712 votes)

    #11 - The Mad Real World

    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(571 votes)

    #12 - Inner City Gang Wars

    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(545 votes)

    #13 - White People Can't Dance

    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 2 Episode 7 - World Series of Dice
    8.0/10(521 votes)

    #14 - World Series of Dice

    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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  15. Chappelle's Show Season 1 Episode 2 - Introducing Tyrone Biggums
    7.9/10(810 votes)

    #15 - Introducing Tyrone Biggums

    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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  16. Chappelle's Show Season 1 Episode 9 - Blackzilla
    7.9/10(607 votes)

    #16 - Blackzilla

    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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  17. Chappelle's Show Season 2 Episode 6 - If The Internet Were Real
    7.9/10(521 votes)

    #17 - If The Internet Were Real

    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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  18. Chappelle's Show Season 1 Episode 4 - Slavery Reparations
    7.8/10(699 votes)

    #18 - Slavery Reparations

    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(671 votes)

    #19 - Great Moments in Hookup History

    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(615 votes)

    #20 - Wu-Tang Consulting Firm

    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(581 votes)

    #21 - The Return of Tyrone Biggums

    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(538 votes)

    #22 - Trading Spouses

    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:Dave Chappelle, Neal Brennan, Nick Kroll, Norman Lear

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  23. Chappelle's Show Season 3 Episode 1 - Lost Episode 1
    7.7/10(413 votes)

    #23 - Lost Episode 1

    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(545 votes)

    #24 - Fisticuffs

    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(717 votes)

    #25 - Love Those Breasts

    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 1142 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".