The 11 Best Chappelle"s Show Skits of All-Time

By CRACKED Writing Staff Jul 19, 2006 183,403 views

While The Lost Episodes of Chappelle' Show have had some funny moments, mostly they've just made us wonder whether Dave quit because of the race stuff or because he was just plain out of material. For the most part, the sketches have covered territory that was dealt with more effectively in years past. The "Race Pixy" skit that allegedly drove Dave to Africa wasn't any more offensive than past skits-it just wasn't as funny. And as Carlos Mencia proves, being both racially offensive and unfunny is a pretty brutal mixture.

On a certain level, the Lost Episodes are disappointing and prove that Dave is fallible, but it' also pretty admirable that he quit rather than work on a show that' creativity had been compromised. In honor of the balls that it took to walk away from $50 million and a once great show, CRACKED counts down the 11 best Chappelle' skits ever. The sketches are embedded below for you to watch. We rank our favorite moment, give you info you might not have known and discuss the lines that were bastardized by white culture. As you'll see, one of the Lost Episode sketches made it, but for the most part it' all the old classics for you to enjoy.

11. REPARATIONS 2003

SEASON 1, EPISODE 4

A sprawling hypothetical scenario that asks what would happen if black people in America were given $1 trillion in reparation money. While some of the humor dwells on the lazy stereotypes that made Chappelle question the show' direction, it also featured some pretty brilliant throw away gags too.
HIGHLIGHT: When it' reported that crime has dropped to 0%, Chappelle, playing a white news reporter, quips: "How could that be-did the Mexicans get money today too?" Noticing he' still on camera, he continues: "I shouldn't have said that (but) I think we'll be alright. Mexicans don't watch the news."
CATCHPHRASES BASTARDIZED BY WHITE PEOPLE: "I'm rich, biotch! HONK." That' right. The audio you heard at the end of every show and on the lips of every frat boy originated in this skit, and it wasn't even Dave who said it. Look for it during the interview with a truck-driving Donnell Rawlings.

10. A MOMENT IN THE LIFE OF LIL' JON

SEASON 2, EPISODE 13

What started as a very funny one-minute sketch in which Chappelle speculated on Lil' Jon' seeming inability to say words other than "H-WHAT?" "YAY-YUH!" and "OH-KAY!" turned into one of the most infectious mono-syllabic comedy refrains since: "D'oh!"
HIGHLIGHTS: Chappelle's Lil' Jon and real-life Lil' Jon interrupt all of the "H-WHATs" and "YAY-YUHs!" to discuss deep cosmic issues like loneliness and having the "feeling that roast beef is the most delicious food."
CATCHPHRASES OVERUSED BY WHITE PEOPLE: The goofy genius of the skit has been drowned out by a nation of suburbanites screaming "Haaaa-what?" "yeah-YA!" and "OH-Kaaaayyyyy!"

9. THE NEW TUPAC SONG

SEASON 3, EPISODE 1

While the majority of Lost Episodes probably should have stayed that way, this skit about Tupac' ever-growing postmortem library is pure genius-although the obnoxious introduction by Donnell Rawlins makes us miss Dave.
HIGHLIGHTS: When Tupac drops a lyric about George W. Bush, but then backpedals and explains that he' only talking about a guy who ran for city council in Oakland in '93.
CATCHPHRASES OVERUSED BY WHITE PEOPLE: We'll see.

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9 Comments

also in the episode where he think's he's Oprahs baby's daddy. Also, the Rick James skit rocks WAY harder than the Prince one. Both are funny though.

0 Replies | Reply | Posted on 7/19/2010 5:58 PM

macfortune

Actually, Dave DOES say "I'm rich, b***h!" in that episode where he's playing video games with the sick kid.

0 Replies | Reply | Posted on 7/19/2010 3:22 AM

thejackyl

wow.. every single video unavailable.

0 Replies | Reply | Posted on 11/22/2008 10:32 AM

bibliophilica

Yay! The list of the 6 funniest broken links! Hilarious!! I love the one with the "This video is no longer available."
Guess that means i love them all the same.

0 Replies | Reply | Posted on 10/4/2008 11:52 AM