The BEST episodes of Chappelle's Show season 2

Every episode of Chappelle's Show season 2, ranked from best to worst by thousands of votes from fans of the show. The best episodes of Chappelle's Show season 2!

"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.

Last Updated: 9/9/2024Network: Comedy CentralStatus: Ended
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True Hollywood Stories - Rick James
star
8.93
717 votes

#1 - True Hollywood Stories - Rick James

Season 2 - Episode 4 - Aired 2/11/2004

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

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The Wayne Brady Show
star
8.44
399 votes

#2 - The Wayne Brady Show

Season 2 - Episode 12 - Aired 4/7/2004

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.

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The Racial Draft
star
8.39
561 votes

#3 - The Racial Draft

Season 2 - Episode 1 - Aired 1/21/2004

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."

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The Niggar Family
star
8.38
443 votes

#4 - The Niggar Family

Season 2 - Episode 2 - Aired 1/28/2004

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.

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True Hollywood Stories - Prince
star
8.16
578 votes

#5 - True Hollywood Stories - Prince

Season 2 - Episode 5 - Aired 2/18/2004

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.

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I Know Black People
star
8.07
270 votes

#6 - I Know Black People

Season 2 - Episode 8 - Aired 3/10/2004

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.

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Black Bush
star
8.01
212 votes

#7 - Black Bush

Season 2 - Episode 13 - Aired 4/14/2004

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.

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Making Da Band
star
8.01
264 votes

#8 - Making Da Band

Season 2 - Episode 10 - Aired 3/25/2004

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.

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World Series of Dice
star
7.98
304 votes

#9 - World Series of Dice

Season 2 - Episode 7 - Aired 3/3/2004

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.

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If The Internet Were Real
star
7.92
326 votes

#10 - If The Internet Were Real

Season 2 - Episode 6 - Aired 2/25/2004

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.

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White People Can't Dance
star
7.74
368 votes

#11 - White People Can't Dance

Season 2 - Episode 3 - Aired 2/4/2004

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.

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Greatest Misses
star
7.71
214 votes

#12 - Greatest Misses

Season 2 - Episode 11 - Aired 3/31/2004

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.

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Oprah's Baby Daddy
star
7.66
286 votes

#13 - Oprah's Baby Daddy

Season 2 - Episode 9 - Aired 3/24/2004

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.

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