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. It's funny even if you don't really get why it's so ironic (IE, if you don't know Wayne Brady).
Complete with finger-shushing the cop as he lays down his corpse, then screaming WOOOOO in the car.
Also, from the very first episode, the Clayton Bigsby sketch, 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.
Also also, the catchphrase-spawning Rick James episode, particularly the real Rick James' "justification" for his behavior: "Cocaine's a hell of a drug."
Also also also, the Racial Draft sketch, when the Asians draft the Wu-Tang Clan: "Konichiwa, bitches!"
Speaking of the Clan: "Diversify yo bonds, nigga!"
Basketball game. Charlie Murphy vs. Prince. And then come the pancakes...
Silky Johnson 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 nowish? *BLAM*
The first time we met the Playa Haters:
Silky: Buck Nasty, what can I say about your suit that hasn't already been said about Afghanistan? It looks bombed out and depleted. As for you, Pitbull, very insulting what you said about my coat... it's made out of your mother's pubic hair. And the so-called Beautiful... why don't you click your heels together three times, and go back to Africa?
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!
Chapelle 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. Croupier: Gambling~ Dave: No thanks. (A pop-up appears, repeating the scene) Bureaucrat: DEBT CONSOLIDATION! Dave: (annoyed grumble) Croupier: Gambling~ Dave: (more annoyed sounding snarl) (Another pop-up appears, repeating the scene) Dave: ''(shouting over Bureaucrat) "DEBT CONSOLIDATION"! NOOOO! God damn! Stop it with all the pop-ups!
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 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."
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".
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!