Chappelle's Show

10 Best Episodes of Chappelle's Show - Season 1

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!

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Chappelle's Show - S1E11

#12 - 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 - S1E4

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

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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 - S1E3

#10 - 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 - S1E7

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

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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 - S1E6

#8 - 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 - S1E9

#7 - Blackzilla (Season 1 - Episode 9)

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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 - S1E8

#6 - The Return of Tyrone Biggums (Season 1 - Episode 8)

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.

The episode was rated 7.91 from 239 votes.

Chappelle's Show - S1E5

#5 - Great Moments in Hookup History (Season 1 - Episode 5)

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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."

The episode was rated 7.97 from 295 votes.

Chappelle's Show - S1E2

#4 - Introducing Tyrone Biggums (Season 1 - Episode 2)

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

The episode was rated 8.00 from 512 votes.

Chappelle's Show - S1E10

#3 - Inner City Gang Wars (Season 1 - Episode 10)

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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.

The episode was rated 8.01 from 213 votes.

Chappelle's Show - S1E12

#2 - Trading Spouses (Season 1 - Episode 12)

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.

The episode was rated 8.04 from 154 votes.

Chappelle's Show - S1E1

#1 - Black White Supremacist (Season 1 - Episode 1)

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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.

The episode was rated 8.15 from 784 votes.

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