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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!

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

Genre:Comedy

Top Episode Highlight

The best episode of "Chappelle's Show" is "True Hollywood Stories - Rick James", rated 9.4/10 from 1058 user votes. It was directed by N/A and written by N/A. "True Hollywood Stories - Rick James" aired on 2/11/2004 and is rated 0.5 point(s) higher than the second highest rated, "The Wayne Brady Show".

  • True Hollywood Stories - Rick James
    9.4/10 1,058 votes

    #1 - True Hollywood Stories - Rick James

    Season 2 Episode 4 - Aired 2004-02-11

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

    Director: N/A

    Writer: N/A

  • The Wayne Brady Show
    8.9/10 635 votes

    #2 - The Wayne Brady Show

    Season 2 Episode 12 - Aired 2004-04-07

    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: N/A

    Writer: N/A

  • True Hollywood Stories - Prince
    8.8/10 621 votes

    #3 - True Hollywood Stories - Prince

    Season 2 Episode 5 - Aired 2004-02-18

    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: N/A

    Writer: N/A

  • Black White Supremacist
    8.6/10 1,068 votes

    #4 - Black White Supremacist

    Season 1 Episode 1 - Aired 2003-01-22

    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: N/A

    Writer: N/A

  • The Racial Draft
    8.6/10 605 votes

    #5 - The Racial Draft

    Season 2 Episode 1 - Aired 2004-01-21

    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: N/A

    Writer: N/A

  • The Niggar Family
    8.4/10 561 votes

    #6 - The Niggar Family

    Season 2 Episode 2 - Aired 2004-01-28

    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: N/A

    Writer: N/A

  • I Know Black People
    8.1/10 473 votes

    #7 - I Know Black People

    Season 2 Episode 8 - Aired 2004-03-10

    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: N/A

    Writer: N/A

  • Making Da Band
    8.1/10 481 votes

    #8 - Making Da Band

    Season 2 Episode 10 - Aired 2004-03-25

    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: N/A

    Writer: N/A

  • Black Bush
    8.1/10 464 votes

    #9 - Black Bush

    Season 2 Episode 13 - Aired 2004-04-14

    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: N/A

    Writer: N/A

  • The Mad Real World
    8.0/10 657 votes

    #10 - The Mad Real World

    Season 1 Episode 6 - Aired 2003-02-26

    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: N/A

    Writer: N/A

  • Inner City Gang Wars
    8.0/10 532 votes

    #11 - Inner City Gang Wars

    Season 1 Episode 10 - Aired 2003-03-26

    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: N/A

    Writer: N/A

  • White People Can't Dance
    8.0/10 505 votes

    #12 - White People Can't Dance

    Season 2 Episode 3 - Aired 2004-02-04

    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: N/A

    Writer: N/A

  • World Series of Dice
    8.0/10 480 votes

    #13 - World Series of Dice

    Season 2 Episode 7 - Aired 2004-03-03

    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: N/A

    Writer: N/A

  • Oprah's Baby Daddy
    8.0/10 441 votes

    #14 - Oprah's Baby Daddy

    Season 2 Episode 9 - Aired 2004-03-24

    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: N/A

    Writer: N/A

  • Introducing Tyrone Biggums
    7.9/10 750 votes

    #15 - Introducing Tyrone Biggums

    Season 1 Episode 2 - Aired 2003-01-29

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

    Director: N/A

    Writer: N/A

  • Blackzilla
    7.9/10 566 votes

    #16 - Blackzilla

    Season 1 Episode 9 - Aired 2003-03-19

    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: N/A

    Writer: N/A

  • If The Internet Were Real
    7.9/10 486 votes

    #17 - If The Internet Were Real

    Season 2 Episode 6 - Aired 2004-02-25

    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: N/A

    Writer: N/A

  • Slavery Reparations
    7.8/10 646 votes

    #18 - Slavery Reparations

    Season 1 Episode 4 - Aired 2003-02-12

    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: N/A

    Writer: N/A

  • Great Moments in Hookup History
    7.8/10 628 votes

    #19 - Great Moments in Hookup History

    Season 1 Episode 5 - Aired 2003-02-19

    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: N/A

    Writer: N/A

  • Wu-Tang Consulting Firm
    7.7/10 570 votes

    #20 - Wu-Tang Consulting Firm

    Season 1 Episode 7 - Aired 2003-03-05

    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: N/A

    Writer: N/A

  • The Return of Tyrone Biggums
    7.7/10 542 votes

    #21 - The Return of Tyrone Biggums

    Season 1 Episode 8 - Aired 2003-03-12

    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: N/A

    Writer: N/A

  • Trading Spouses
    7.7/10 503 votes

    #22 - Trading Spouses

    Season 1 Episode 12 - Aired 2003-04-09

    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: N/A

    Writer: N/A

  • Lost Episode 1
    7.7/10 391 votes

    #23 - Lost Episode 1

    Season 3 Episode 1 - Aired 2006-07-09

    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: N/A

    Writer: N/A

  • Fisticuffs
    7.6/10 510 votes

    #24 - Fisticuffs

    Season 1 Episode 11 - Aired 2003-04-02

    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: N/A

    Writer: N/A

  • Love Those Breasts
    7.5/10 665 votes

    #25 - Love Those Breasts

    Season 1 Episode 3 - Aired 2003-02-05

    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: N/A

    Writer: N/A