- From the very first episode, the Clayton Bigsby, especially its hilarious final line (just see it for yourself).
- The moment when the leading voice of the white supremacist movement is revealed to be black to the public. The sheer mind bending-ness of the whole thing really hits home in that instant of dumbstruck silence. Especially when one of the members of the audience is simply unable to process it, and his head explodes.
- 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!"
- The White Delegation tries to draft Colin Powell, which is odd considering he's 100% black ("He's not even an eighth white!"). The Black Delegation agrees to it, but only if they take Condolezza Rice too.
- Speaking of the Clan, the Wu Tang Financial skit:
- Basketball game. Charlie Murphy vs. Prince. And then come the pancakes...
- 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?"
- Later, Dave recalls R. Kelly's immediate reaction to seeing the video:
- 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 Playa Haters' Ball is packed with great lines:
Silky Johnson: The Playa Hater's Ball gives us an opportunity to hate on a diverse array of mark-ass marks, trick-ass marks, punk bitches, and skip-skap skanks and scallywags, hos, heifers, hee-haws, and hootie-hoos.
- Silky Johnson explaining the purpose of the Playa Haters' Ball.
- Ice-T appears As Himself to host the ceremony. He gets some hecklers tossing out Flowery Insults like "You look like Bill Cosby on crack!" and "You look like a bootleg Ice-T!" He takes it in stride, though... for the most part...Pit Bull: Man, you CORNY!
Ice-T: Next nigga to say something while I'm talking is getting shot. Please believe that.
- There's also when Silky Johnson first meets up with Buc Nasty, Beautiful, and Pit Bull before the ceremony and they start sniping at each other's Pimp Duds.Buc Nasty: Man, you oughta take that cane and beat whoever made that suit to death.
Pit Bull: Why don't you vacuum that coat, man?
Silky: Well, well, well... the most diabolical haters this side of the Mississippi... 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.
- Then Ice-T Presents the nominees for the "Hater of the Year" award...Ice-T: First up, Buc Nasty!
Buc Nasty: Clap for me, bitch!
Ice-T: Buc Nasty is nominated for... getting his best friend's wife pregnant, then tricking his best friend into raising the little motherfucker!
Buc Nasty: Yeah, holla atcha boy!
Ice-T: Damn, that's hateful! The next nominee is Pit Bull! (audience boos) Pit Bull is nominated for calling the police on the drug dealers that moved next door to his house — NOT because it was the right thing to do, [but] just because he was jealous of all the money they was makin'!
Pit Bull: Pit BULL! (barks)
Ice-T: Finally, the one and only Silky Johnson! (mixed boos and applause from the crowd) Silky Johnson is nominated for calling in a bomb threat to the Special Olympics, man!
- Then, of course, Silky wins the award to heavy boos from the audience. His acceptance speech, and the other haters' reactions to it, are a sight to behold.Pit Bull: Kiss my ass! I'M THE BIGGEST HATER!
(Silky Johnson goes up to the stage accept his award)
Beautiful: Silky's meat made out of 100% rat ass! (to one of his lady friends) Hit me, baby. (she sprays his hair for him)
Silky Johnson: That, of course, was Beautiful talking. Beautiful on the weekends does stunts for Little Richard in gay movies. First off, I would like to thank God almighty for giving everybody so much... and me, so little. (everyone boos him; he addresses random audience members) I hate you; I hate you; I don't even know you and I hate your guts! I hope all the bad things in life happen to you and nobody else but you... (more booing from the crowd)
Audience: (chanting) HATE! HATE! HATE! HATE! HATE! HATE!
Silky Johnson: And as I sip my soda that I'm sure somebody spit in, I just would like to say to all of you... kiss my ass, you rotten motherfuckers! (more booing from the crowd) Now if you'll excuse me, I'm gonna go home and put some water in Buc Nasty's momma's dish.
- 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)
Bureaucrat: DEBT CONSOLIDATION!
Dave: No thanks.
(A pop-up appears, repeating the scene)
Bureaucrat: DEBT CONSOLIDATION!
Dave: (annoyed grumble)
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 "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.)
DJ: Tupac, rest in peace.Tupac: Okay, I will!
- 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:
- 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!
- Tron Carter pleads the "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:Jackson: HOW'S IT TASTE, MOTHERFUCKER?Customer: Could you please stop yelling at me?Jackson: NO, I CAN'T STOP YELLING, 'CUZ THAT'S HOW I TALK! YOU AIN'T EVER SEEN MY MOVIES?
- 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).
Brady: I make Bryant Gumbel look like Malcolm X, huh, motherfucker?Dave: It was Mooney!note
- "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.
- 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)
Grandma: This nukkuh here talmbout keepin' it real? I'mo keep it real - I want his goddamn ass outta my house! I'm tryna get my swerve on too! Shit...(later)Narrator: He is witness to things that no man should ever have to see.Grandma: (making out with hookup while Darius zones out nearby) Darius, you big dummy, this ain't no show-and-tell! Take a walk!Hookup: Yeah, and get some rubbers!Grandma: And get the big ones.Hookup: Fuckin' right.
- The humiliation that Darius regularly endures at his grandmother's house.
Inmate: What's really hood, bitch?Narrator: Brenda knew it was important to establish her realness early in prison. Confronted by another pivotal decision, she decided then and there to keep it real.Brenda: (gets in inmate's face) Alright bitch, let's settle this right now.(No-Holds-Barred Beatdown on Brenda from multiple inmates ensues)Narrator: The three women were all serving consecutive life sentences. It turned out they kept it realer.
- The prisoner attempting to start shit with Brenda and the ensuing results.
Funny / Chappelle's Show