Chappelle's Show

10 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.

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 - S1E5

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

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 - S2E7

#14 - World Series of Dice (Season 2 - Episode 7)


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.

The episode was rated 7.99 from 159 votes.

Chappelle's Show - S1E2

#13 - 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

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


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 - S2E6

#11 - If The Internet Were Real (Season 2 - Episode 6)

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.

The episode was rated 8.03 from 156 votes.

Chappelle's Show - S2E10

#10 - Making Da Band (Season 2 - Episode 10)


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.

The episode was rated 8.03 from 153 votes.

Chappelle's Show - S1E12

#9 - 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 - S2E13

#8 - Black Bush (Season 2 - Episode 13)


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.

The episode was rated 8.05 from 130 votes.

Chappelle's Show - S2E8

#7 - I Know Black People (Season 2 - Episode 8)

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.

The episode was rated 8.07 from 151 votes.

Chappelle's Show - S2E2

#6 - The Niggar Family (Season 2 - Episode 2)


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.

The episode was rated 8.08 from 249 votes.

Chappelle's Show - S2E1

#5 - The Racial Draft (Season 2 - Episode 1)

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."

The episode was rated 8.10 from 264 votes.

Chappelle's Show - S1E1

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


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.

Chappelle's Show - S2E5

#3 - True Hollywood Stories - Prince (Season 2 - Episode 5)

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.

The episode was rated 8.33 from 341 votes.

Chappelle's Show - S2E12

#2 - The Wayne Brady Show (Season 2 - Episode 12)


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.

The episode was rated 8.42 from 204 votes.

Chappelle's Show - S2E4

#1 - True Hollywood Stories - Rick James (Season 2 - Episode 4)

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

The episode was rated 8.57 from 442 votes.

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