The BEST Episodes of Chappelle's Show

Every episode ever - ranked by fan votes!

Last Updated: Jul 1, 2021

Network: Comedy Central

"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.

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True Hollywood Stories - Rick James

#1 - True Hollywood Stories - Rick James

Season 2 - Episode 4 - Aired Feb 11, 2004

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

star 8.94
753 votes
Trading Spouses

#2 - Trading Spouses

Season 1 - Episode 12 - Aired Apr 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.

star 8.76
412 votes
Writers: Dave Chappelle, Neal Brennan
The Wayne Brady Show

#3 - The Wayne Brady Show

Season 2 - Episode 12 - Aired Apr 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.

star 8.50
400 votes
The Niggar Family

#4 - The Niggar Family

Season 2 - Episode 2 - Aired Jan 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.

star 8.46
448 votes
The Racial Draft

#5 - The Racial Draft

Season 2 - Episode 1 - Aired Jan 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."

star 8.44
576 votes

#6 - Fisticuffs

Season 1 - Episode 11 - Aired Apr 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.

star 8.37
398 votes
Writers: Dave Chappelle, Neal Brennan
Introducing Tyrone Biggums

#7 - Introducing Tyrone Biggums

Season 1 - Episode 2 - Aired Jan 29, 2003

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

star 8.37
880 votes
Writers: Dave Chappelle, Neal Brennan
Inner City Gang Wars

#8 - Inner City Gang Wars

Season 1 - Episode 10 - Aired Mar 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.

star 8.32
474 votes
Writers: Dave Chappelle, Neal Brennan
Black White Supremacist

#9 - Black White Supremacist

Season 1 - Episode 1 - Aired Jan 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.

star 8.29
1,256 votes
Writers: Dave Chappelle, Neal Brennan
The Mad Real World

#10 - The Mad Real World

Season 1 - Episode 6 - Aired Feb 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.

star 8.23
576 votes
Writers: Dave Chappelle, Neal Brennan
True Hollywood Stories - Prince

#11 - True Hollywood Stories - Prince

Season 2 - Episode 5 - Aired Feb 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.

star 8.18
597 votes
I Know Black People

#12 - I Know Black People

Season 2 - Episode 8 - Aired Mar 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.

star 8.17
261 votes
The Return of Tyrone Biggums

#13 - The Return of Tyrone Biggums

Season 1 - Episode 8 - Aired Mar 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.

star 8.16
499 votes
Writers: Dave Chappelle, Neal Brennan
Making Da Band

#14 - Making Da Band

Season 2 - Episode 10 - Aired Mar 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.

star 8.14
263 votes
Wu-Tang Consulting Firm

#15 - Wu-Tang Consulting Firm

Season 1 - Episode 7 - Aired Mar 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.

star 8.13
553 votes
Writers: Dave Chappelle, Neal Brennan
Black Bush

#16 - Black Bush

Season 2 - Episode 13 - Aired Apr 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.

star 8.11
209 votes
World Series of Dice

#17 - World Series of Dice

Season 2 - Episode 7 - Aired Mar 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.

star 8.10
298 votes
Slavery Reparations

#18 - Slavery Reparations

Season 1 - Episode 4 - Aired Feb 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.

star 8.09
694 votes
Writers: Dave Chappelle, Neal Brennan
Great Moments in Hookup History

#19 - Great Moments in Hookup History

Season 1 - Episode 5 - Aired Feb 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."

star 8.01
588 votes
Writers: Dave Chappelle, Neal Brennan
If The Internet Were Real

#20 - If The Internet Were Real

Season 2 - Episode 6 - Aired Feb 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.

star 8.01
319 votes

#21 - Blackzilla

Season 1 - Episode 9 - Aired Mar 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.

star 7.99
486 votes
Writers: Dave Chappelle, Neal Brennan
Lost Episode 3

#22 - Lost Episode 3

Season 3 - Episode 3 - Aired Jul 23, 2006

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

star 7.97
178 votes
White People Can't Dance

#23 - White People Can't Dance

Season 2 - Episode 3 - Aired Feb 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.

star 7.85
366 votes
Oprah's Baby Daddy

#24 - Oprah's Baby Daddy

Season 2 - Episode 9 - Aired Mar 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.

star 7.78
277 votes
Love Those Breasts

#25 - Love Those Breasts

Season 1 - Episode 3 - Aired Feb 5, 2003

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.

star 7.72
717 votes
Writers: Dave Chappelle, Neal Brennan