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 Chappelle' Show with impunity.
7. BLACK GEORGE BUSH
SEASON 2, EPISODE 13In 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 fuck up."
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 1The 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.
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 6In 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
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.
CATCHPHRASE OVERUSED BY WHITE PEOPLE: "Katie had some big ass tit-tays."
4. WAYNE BRADY
SEASON 2, EPISODE 12The 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 fucker 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.
CATCHPHRASES OVERUSED BY WHITE PEOPLE: "Is Wayne Brady gonna have to choke a bitch?"
3. THE RACIAL DRAFT
SEASON 2, EPISODE 1A 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.
2. CHARLIE MURPHY'S TRUE HOLLYWOOD STORIES: RICK JAMES
SEASON 2, EPISODE 4Chances 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, bitch!" 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"
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."
CATCHPHRASE OVERUSED BY WHITE PEOPLE: "I'm Rick James, bitch!"
1. CHARLIE MURPHY'S TRUE HOLLYWOOD STORIES: PRINCE
SEASON 2, EPISODE 5Arriving 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.
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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