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

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.


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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."
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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.
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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."
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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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8. LOST EPISODE OF FEAR FACTOR

SEASON 2, EPISODE 12

"Tyrone the Crackhead" becomes a contestant on Fear Factor and real-life host Joe Rogan appears in a cameo that almost makes him seem funny. Is it wrong for white folks to laugh at a caricature of a black drug addict? We're not sure, but to Chappelle' credit, it' impossible not to.
HIGHLIGHT: Chappelle' insistence on calling the host by his full name whenever addressing him as when he says, "I'm gonna tell you something about me, Joe Rogan, that you might not know. I smoke rocks."
CATCHPHRASES OVERUSED BY WHITE PEOPLE: Ummm, yeah it' pretty much that last one. Fortunately, most of our editors are three-hundred pound black men so we're allowed to quote
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Chappelle' Show with impunity.
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7. BLACK GEORGE BUSH

SEASON 2, EPISODE 13

In the "Black Bush" sketch, Chappelle assumes the role of, well, a black President Bush. There' also a black Tony Blair (Jamie Foxx!) and a black head of the CIA (Mos Def!) to boot. Mixed with actual TV footage, the mock-leaders give frank answers to reporters' hard-hitting questions. Hearing Chappelle' blunt interpretation of Bush' logic, and not the race jokes, is what makes this skit fly. For instance"
HIGHLIGHTS: [To the U.N.] "If you have a problem with that, you know what you should do? You should sanction me. Sanction me with your army. Oh, wait a minute, you don't have an army. I guess that means you need to shut the f**k up."
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CATCHPHRASES OVERUSED BY WHITE PEOPLE: The part where Chappelle says Saddam, "very possibly has weapons of mass destruction." We heard this one white guy quote that line on TV once and it was one time too many.

6. THE BLACK KLAN LEADER

SEASON 1, EPISODE 1

The sketch that set the tone for the entire series came early-like first episode early. Chappelle showed in his premiere that he wasn't afraid of race-or racism-when he played the world' only black white supremacist, a blind man named Clayton Bigsby.
HIGHTLIGHT: After Bigsby finds out that he' actually black, he leaves his wife for being n*gger-lover.
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CATCHPHRASES OVERUSED BY WHITE PEOPLE: Actually, we're pretty certain no white people were stupid enough to use the phrases from this sketch.

5. THE MAD REAL WORLD

SEASON 1, EPISODE 6

In the introduction to this sketch, Chappelle observes that it' no wonder why black people are always getting kicked off of MTV' The Real World. If they did the opposite and put a white person in a house full of the craziest black people they could find, that white person wouldn't fair so well either. The sketch uses the chubby white guy from Best Week Ever to determine what happens when people start getting mad real.
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HIGHLIGHT: Charlie Murphy brings a hilarious authenticity to his ex-con, like when he insists that his roommate pee sitting down and conducts the most convincing prison shivving this side of Attica.
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CATCHPHRASE OVERUSED BY WHITE PEOPLE: "Katie had some big ass tit-tays."

4. WAYNE BRADY

SEASON 2, EPISODE 12

The Wayne Brady episode is the concept album of Chappelle's Show episodes: a single comedic premise that runs throughout the entire show and pays off with one of the most unexpected skits of the show's two-season run. Not only did they write a genius sketch in which Wayne Brady' image is turned on its head, but they also got the f****r to star in it.
HIGHLIGHT: The concept of an evil Wayne Brady was made even funnier when Brady nailed all of the small gestures of a cold-blooded killer-like when he whispers "Shhhh" in the cop' ear after snapping his neck.
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CATCHPHRASES OVERUSED BY WHITE PEOPLE: "Is Wayne Brady gonna have to choke a b***h?"

3. THE RACIAL DRAFT

SEASON 2, EPISODE 1

A brilliant premise that is perfectly executed, this skit imagines which celebrities would be drafted by which races. In addition to some hilarious commentary from Chappelle and the other pundits narrating the procession, some of the picks-like the Chinese choosing the Wu Tang Clan-make this one of the best skits ever.
HIGHLIGHT: The little finger-wiggling hand shake the two white pundits give each other upon reporting that the white race has traded away OJ.
CATCHPHRASES OVERUSED BY WHITE PEOPLE: "If white people knew they were going to get away with picking a black person, I bet they would have picked Oprah." Although we've never heard a white person quote it, our parents laughed entirely too hard at this one.
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2. CHARLIE MURPHY'S TRUE HOLLYWOOD STORIES: RICK JAMES

SEASON 2, EPISODE 4

Chances are, if you have any friends that are white males between the ages 12-35 with cable television, you're familiar with the line, "I'm Rick James, b***h!" Even months after the episode aired, kids were still dropping that line at every possible opportunity. But people often overlook the other groin-grabbingly amazing parts of this skit, like"
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HIGHLIGHT: Chappelle, as Rick James, spitefully calling Charlie Murphy "Darkness" and, after receiving a karate kick to the torso, saying "Now that you mention it, I think I'm bleeding in my chest."
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CATCHPHRASE OVERUSED BY WHITE PEOPLE: "I'm Rick James, b***h!"

1. CHARLIE MURPHY'S TRUE HOLLYWOOD STORIES: PRINCE

SEASON 2, EPISODE 5

Arriving just one week after the instant classic Rick James episode, we were certain that Chappelle was looking a gift horse in the mouth and asking for more. Another Charlie Murphy' True Hollywood Story already? It' too much too soon! There' no way this one lives up to Rick James. But then things started happening: Chappelle' Prince keeps making creepy eye contact with the camera, he humps the ball in the middle of a particularly foggy game of pickup basketball and to wrap it all up, he serves Charlie Murphy pancakes. By the end of the skit, we didn't know what had just happened. We just knew it was genius.
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HIGHLIGHT: Almost too many to count, but the close up of Prince' face after Charlie Murphy insults him (3:02 on above YouTube video) is pretty priceless.
CATCHPHRASE OVERUSED BY WHITE PEOPLE: Not too many overused phrases from this one which, in addition to its much shorter running time, gave it the edge over the Rick James sketch. Every once in a while when you're playing pickup hoops, the guy bringing the ball up the court will call out "computer blue," pass you the ball and yell "shoot the J, shoot it." But we're pretty sure that' never going to get old.
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