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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!

The Best Episodes of Chappelle's Show

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

Seasons3

  1. Background image for True Hollywood Stories - Rick James
    9.4/10(1.1k 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.

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    Director:Unknown
    Writer:Unknown
  2. Background image for The Wayne Brady Show
    9.0/10(667 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.

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    Director:Unknown
    Writer:Unknown
  3. Background image for True Hollywood Stories - Prince
    8.8/10(660 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.

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    Director:Unknown
    Writer:Unknown
  4. Background image for Black White Supremacist
    8.6/10(1.1k 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.

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    Director:Unknown
    Writer:Unknown
  5. Background image for The Racial Draft
    8.6/10(633 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."

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    Director:Unknown
    Writer:Unknown
  6. Background image for The Niggar Family
    8.4/10(594 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.

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    Director:Unknown
    Writer:Unknown
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    The 20 WORST Episodes of Chappelle's Show

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  8. Background image for I Know Black People
    8.1/10(502 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.

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    Director:Unknown
    Writer:Unknown
  9. Background image for Oprah's Baby Daddy
    8.1/10(469 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.

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    Director:Unknown
    Writer:Unknown
  10. Background image for Making Da Band
    8.1/10(509 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.

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    Director:Unknown
    Writer:Unknown
  11. Background image for Black Bush
    8.1/10(490 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.

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    Director:Unknown
    Writer:Unknown
  12. Background image for The Mad Real World
    8.0/10(689 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.

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    Director:Unknown
    Writer:Unknown
  13. Background image for Inner City Gang Wars
    8.0/10(556 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.

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    Director:Unknown
    Writer:Unknown
  14. Background image for White People Can't Dance
    8.0/10(529 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.

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    Director:Unknown
    Writer:Unknown
  15. Background image for World Series of Dice
    8.0/10(505 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.

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    Director:Unknown
    Writer:Unknown
  16. Background image for Introducing Tyrone Biggums
    7.9/10(787 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.

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    Director:Unknown
    Writer:Unknown
  17. Background image for Blackzilla
    7.9/10(591 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.

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    Director:Unknown
    Writer:Unknown
  18. Background image for If The Internet Were Real
    7.9/10(508 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.

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    Director:Unknown
    Writer:Unknown
  19. Background image for Slavery Reparations
    7.8/10(680 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.

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    Director:Unknown
    Writer:Unknown
  20. Background image for Great Moments in Hookup History
    7.7/10(654 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."

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    Director:Unknown
    Writer:Unknown
  21. Background image for Wu-Tang Consulting Firm
    7.7/10(599 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.

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    Director:Unknown
    Writer:Unknown
  22. Background image for The Return of Tyrone Biggums
    7.7/10(566 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.

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    Director:Unknown
    Writer:Unknown
  23. Background image for Trading Spouses
    7.7/10(525 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.

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  24. Background image for Lost Episode 1
    7.7/10(406 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.

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    Director:Unknown
    Writer:Unknown
  25. Background image for Fisticuffs
    7.6/10(531 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.

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    Director:Unknown
    Writer:Unknown
  26. Background image for Greatest Misses
    7.6/10(446 votes)

    #25 - Greatest Misses

    S2:E11

    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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    Director:Unknown
    Writer:Unknown

Best Episodes Summary

"True Hollywood Stories - Rick James" is the best rated episode of "Chappelle's Show". It scored 9.4/10 based on 1113 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".