Funny / Chappelle's Show

  • From the very first episode, the Clayton Bigsby, especially its hilarious final line (just see it for yourself).
  • The catchphrase-spawning Rick James episode, particularly the real Rick James' "justification" for his behavior: "Cocaine's a hell of a drug."
    (Real) Rick James: "I mean, what am I gonna do, just jump up and grind my feet into somebody's couch like it's something to do? Come on, I have a little more sense than that. (beat) Yeah, I remember grinding my feet in Eddie's couch."
  • The Racial Draft sketch, when the Asians draft the Wu-Tang Clan: "Konichiwa, bitches!"
    GZA: "You gotta diversify yo bonds, nigga!"
  • Basketball game. Charlie Murphy vs. Prince. And then come the pancakes...
    Prince: (after scoring the final point) Game—blouses.
  • Haters wanna hate. Lovers wanna love. I don't even want, none of the above. I want to piss on you!
    • Later, Dave recalls R. Kelly's immediate reaction to seeing the video:
      R. Kelly: "Dave, how you gon' make a video about peeing on somebody?"
      Dave: "Nigga, how you gon' make a video about peeing on somebody?"
  • Silky Johnston shooting the slave master in the unused "Time Haters" skit was fucking hilarious.
    Slave: But when's we gonna be free?!
    Silky: That is a good question, my man. How about now-ish? *BLAM*
    • The first time we met the Playa Haters:
    Silky: Buc Nasty, what can I say about your suit that hasn't already been said about Afghanistan? It looks bombed out and depleted. And the so-called Beautiful... why don't you click your heels together three times, and go back to Africa? As for you, Boss Hogg, very insulting what you said about my coat... it's made out of your mother's pubic hair. All white and silky.
  • The "White People Can't Dance" skit, where they try and disprove the aforementioned notion. Dave having John Mayer play electric guitar in very professional and posh settings, and ?uestlove playing drums in a barber shop in Harlem.
    Dave: (in a five-star restaurant) Play the one—the fight riff! Go! GO!
    • When the cops come to stop them, John Mayer distracts them by playing "Every Rose Has Its Thorn"...and Dave's surprised to see the black cop dancing along. "Hey man, I grew up in the suburbs."
  • Chappelle imagines a world where the Internet is a real place.
    (Dave walks by an Obstructive Bureaucrat and a roulette croupier)
    Dave: No.
    Croupier: Gambling~
    Dave: No thanks.
    (A pop-up appears, repeating the scene)
    Dave: (annoyed grumble)
    Croupier: Gambling~
    Dave: (more annoyed sounding snarl)
    (Another pop-up appears, repeating the scene)
    Dave: ''(shouting over Bureaucrat) "DEBT CONSOLIDATION"! "GAMBLING"! ENOUGH! ENOUGH WITH THE POP-UPS! Dicks!
    • At the end of the skit...
    (The same scene with the Obstructive Bureaucrat and a roulette croupier, this time, Dave punches both of them out as he enters)
  • The "holla atcha bitch!" guy. In one of the Hilarious Outtakes, they told the guy to go nuts, and he had everyone on the set rolling.
  • Tyrone Biggums gives a Drug Awareness seminar at an elementary school classroom and becomes the perfect Anti-Role Model for the captive crowd.
    Teacher: I can definitely say he was the absolute worst anti-drug speaker in the history of drugs.
  • In a later episode, he effortlessly makes it to the finals of Fear Factor:
    Tyrone: "I'm gonna tell you something about me, Joe Rogan, that you might not know. I smoke rocks."
  • In another Tyrone skit, he drinks a new "energy drink" called Red Balls, which enables him to smash his way out of prison. Then he runs back into his cell to steal the bed-pillow.
  • The Lil Jon sketches, especially the one with the REAL Lil' Jon.
    • The best part was the real Lil' Jon could do the deep English actor voice too.
  • The scene where everyone in the nightclub dances along to a "new" Tupac joint, with the song making references to things that happened after the real Tupac was murdered (Eminem, Grand Theft Auto: San Andreas, etc.)
    • On the second verse, Tupac laments, "What can a nigga do/When half the people voted for George W?" Everyone stops and looks around suspiciously, only to go back to dancing when he explains he was talking about a guy named George W. Smith... "He ran in '93 out in Oakland/You probably didn't hear about him".
    • The song ends thus:
    DJ: Tupac, rest in peace.
    Tupac: Okay, I will!
  • On the Season 2 blooper reel, Dave's baby starts crying while he and Wayne Brady are filming their sketch:
    Dave: Sorry everyone...(Beat) That's my baby, y'all can't say SHIT!
  • Fif.
  • The commercial bumpers where the two old men are singing and playing a harmonica? With a hat turned up for tips from passers-by? In one of them, Dave runs out, slaps a bill into the hat, strikes a pose, and shouts/sings "BETTER NOT BRING YO' KIDS~!"
  • "Black Bush". The Iraq War gets satirized as only Dave can. Featuring Jamie Foxx as Black Tony Blair.
  • The promo video sketch for the "turn my headphones up" mix-tape, in which the artist has two sidekicks making extremely bombastic claims about the popularity of his work, which is just him constantly demanding in slightly different ways to turn up the volume of the backing music. The punchline is that the artist got shot in the ear several times, and really is unable to hear the beat.
    Sidekick #1: It's not going double platinum, it's going double uranium!
    Sidekick #2: Uranium.
  • Kneehigh Park. The entire thing...
  • The Samuel Jackson Beer sketch, where Dave, as Samuel L. Jackson (dressed in a colonial outfit), pitches his namesake beer while yelling at the top of his lungs:
    Customer: Could you please stop yelling at me?
  • The Training Day parody with Wayne Brady, where he's revealed to be a dangerous sociopath — gunning down a guy with an AK-47, pimping, forcing Dave to smoke Angel Dust, and forcing him to give him his sandwich. It's funny even if you don't really get why it's so ironic (IE, if you don't know Wayne Brady).
    • "Is Wayne Brady gonna have to choke a bitch?"
    • The clincher is using his white-friendly appeal to get out a traffic ticket... only to immediately snap the cop's neck, complete with finger-shushing the cop as he lays down his corpse, then screaming WOOOOO! in the car.
    Brady: I make Bryant Gumbel look like Malcolm X, huh, motherfucker?
    Dave: It was Mooney!note 
  • In the wake of losing control of his show to Brady, Dave calls Big Boi from Outkast to try and hang out with him. Big Boi responds by making lame excuses as to why the two can no longer hang out, including playing tennis with Don Cornelius...on the moon.
  • The final aired sketch where Dave meets Show Business. All the short skits are really funny, but one moment stands out when Dave is feeling nervous in the lobby.
    Secretary: Don't worry. Everyone's a little nervous when they meet Show Business...except P. Diddy.
  • All three of the "When Keeping It Real Goes Wrong" sketches.
    Narrator: What Darius didn't know was that Chris was a tenth-degree black belt who started trouble just so he could practice his karate in street-fighting scenarios. What ensued was one of the most spectacular ass-whoopings ever witnessed in the Atlantic Northeast. Viewer discretion is advised. (No-Holds-Barred Beatdown ensues)