Chappelle's Show

10 Worst 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.

Written by Sophie and last updated on jan 18, 2023.

PS: The following content contains spoilers!

PPS: I will admit that parts of this page was written with the help of AI - it makes my work so much easier to not start from a blank page!

Chappelle's Show - S1E9

#10 - Blackzilla (Season 1 - Episode 9)

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.

The episode was rated 7.90 from 225 votes.

Chappelle's Show - S1E6

#9 - The Mad Real World (Season 1 - Episode 6)


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.

The episode was rated 7.87 from 307 votes.

Chappelle's Show - S2E3

#8 - White People Can't Dance (Season 2 - Episode 3)

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.

The episode was rated 7.83 from 195 votes.

Chappelle's Show - S1E7

#7 - Wu-Tang Consulting Firm (Season 1 - Episode 7)


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.

The episode was rated 7.82 from 232 votes.

Chappelle's Show - S1E3

#6 - Love Those Breasts (Season 1 - Episode 3)

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.

The episode was rated 7.77 from 388 votes.

Chappelle's Show - S1E4

#5 - Slavery Reparations (Season 1 - Episode 4)


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.

The episode was rated 7.75 from 385 votes.

Chappelle's Show - S1E11

#4 - Fisticuffs (Season 1 - Episode 11)

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.

The episode was rated 7.74 from 167 votes.

Chappelle's Show - S2E9

#3 - Oprah's Baby Daddy (Season 2 - Episode 9)


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.

The episode was rated 7.71 from 137 votes.

Chappelle's Show - S3E2

#2 - Lost Episode 2 (Season 3 - Episode 2)

Dave hits the campaign trail as yell-happy presidential candidate Howard Dean and assumes the role of an antagonistic Gary Coleman. He also attempts to elude a crop of persistent racial stereotype pixies.

The episode was rated 7.70 from 102 votes.

Chappelle's Show - S2E11

#1 - Greatest Misses (Season 2 - Episode 11)


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.

The episode was rated 7.49 from 121 votes.

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