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1* From the very first episode, the [[https://www.youtube.com/watch?v=JBC-9k3y1ew Clayton]] [[https://www.youtube.com/watch?v=D7oXFmuUHLQ Bigsby]] sketch, especially its hilarious final line (just see it for yourself).
2** The moment when the leading voice of the white supremacist movement is [[YouAreWhatYouHate revealed to be black]] to the public. The sheer mind bending-ness of the whole thing really hits home in that instant of [[StunnedSilence dumbstruck silence]]. Especially when one of the members of the audience is [[LogicBomb simply unable to process it]], and [[YourHeadASplode his head explodes]].
3* The [[FountainOfMemes catchphrase-spawning]] Rick James episode, particularly the real Rick James' "justification" for his behavior: "Cocaine's a hell of a drug."
4-->'''(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."
5-->[the footage gets rewinded and repeated]
6* The outtakes are of special mention by themselves:
7-->'''Dave Chappelle!Rick James:''' "I'm a maniac, maniac on yo' couch!"
8-->'''Dave Chappelle!Rick James:''' "What'd get a nice white couch for anyway? You only gonna get your big black ass on it!"
9-->'''Dave Chappelle!Rick James:''' "Stop. Beating. Me. Into. ''UNITY''!"
10* The Racial Draft sketch, when the Asians draft the Music/WuTangClan: "Konichiwa, bitches!"
11** The White Delegation tries to draft Colin Powell, which is odd considering he's 100% black ("He's not even an eighth white!"). [[TakeThat The Black Delegation agrees to it, but only if they take Condolezza Rice too]].
12** Speaking of the Clan, the Wu Tang Financial skit:
13--> '''GZA:''' "You gotta diversify yo bonds, nigga!"
14** The Black Delegation asking for Music/{{Eminem}}, with the White Delegation not wanting to give him up. They instead settle on OJ Simpson.
15* Basketball game. Charlie Murphy vs. ''Music/{{Prince}}''. And then come the pancakes...
16-->'''Music/{{Prince}}''': ''(after scoring the final point)'' Game--''[[InsultBackfire blouses]]''.
17** And after that slam dunk, what the hell was keeping Prince up t... oh.
18** TruthInTelevision: Prince [[http://deadspin.com/prince-was-an-afro-rocking-coach-hating-high-school-ba-1689252341 was a good player on his high school squad]]. That cat ''could'' ball.
19** Meta example: the fact that Prince used the picture of Dave dressed as him as [[https://en.wikipedia.org/wiki/Breakfast_Can_Wait#/media/File:Breakfastwait.jpg a cover for one of his singles]].
20--->'''Dave:''' That's a Prince judo move right there... You make fun of Prince in a sketch and he'll just use you in his album cover... What am I going to do—sue him for using a picture of me dressed up like him?... That's checkmate right there.
21* [[https://www.youtube.com/watch?v=eafRE74JGZ8 Haters wanna hate. Lovers wanna love. I don't even want, none of the above. I want to piss on you!]]
22** Later, Dave recalls Music/RKelly's immediate reaction to seeing the video:
23--->'''R. Kelly:''' "Dave, how you gon' make a video about peeing on somebody?"\
24'''Dave:''' "Nigga, how ''you'' gon' make a video about peeing on somebody?"
25* Silky Johnson shooting the slave master in the unused "Time Haters" skit was ''fucking hilarious''.
26-->'''Slave:''' But when's we gonna be free?!
27-->'''Silky:''' That is a good question, my man. How about now-ish? '''*BLAM*'''
28* The Playa Haters' Ball is packed with great lines:
29** Silky Johnson explaining the purpose of the Playa Haters' Ball.
30-->'''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.
31** Music/IceT appears AsHimself to host the ceremony. He gets some hecklers tossing out FloweryInsults like "You look like Creator/BillCosby on crack!" and "[[YourCostumeNeedsWork You look like a bootleg Ice-T]]!" He takes it in stride, though... for the most part...
32--->'''Pit Bull:''' Man, you CORNY!\
33'''Ice-T:''' [[DisproportionateRetribution Next nigga to say something while I'm talking is getting shot. Please believe that.]]
34** 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 PimpDuds.
35--->'''Buc Nasty:''' Man, you oughta take that cane and beat whoever made that suit to death.\
36'''Pit Bull:''' Why don't you vacuum that coat, man?\
37'''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 [[Film/TheWizardOfOz 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.
38** Then Ice-T Presents the nominees for the "Hater of the Year" award...
39--->'''Ice-T:''' First up, Buc Nasty!\
40(''audience boos'')\
41'''Buc Nasty:''' Clap for me, bitch!\
42'''Ice-T:''' Buc Nasty is nominated for... getting his best friend's wife pregnant, then tricking his best friend into ''raising'' the little motherfucker!\
43(''audience boos'')\
44'''Buc Nasty:''' Yeah, holla atcha boy!\
45'''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'!''\
46'''Pit Bull:''' Pit BULL! (''barks'')\
47'''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!''
48** 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.
49--->'''Pit Bull:''' [[SoreLoser Kiss my ass! I'M THE BIGGEST HATER!]]\
50(''Silky Johnson goes up to the stage accept his award'')\
51'''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'')\
52'''Silky Johnson:''' That, of course, was Beautiful talking. Beautiful on the weekends does stunts for Music/LittleRichard 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'')\
53'''Audience:''' (''chanting'') HATE! HATE! HATE! HATE! HATE! HATE!\
54'''Silky Johnson:''' And as I sip my soda [[RevengeIsADishBestServed 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 [[StealthInsult put some water in Buc Nasty's momma's dish.]] Good evening.
55* The "White People Can't Dance" skit, where they try and disprove the aforementioned notion. Dave having Music/JohnMayer play electric guitar in very professional and posh settings, and ?uestlove playing drums in [[CrossesTheLineTwice a barber shop in Harlem]].
56-->'''Dave''': ''(in a five-star restaurant)'' Play the one--the fight riff! Go! GO!
57** 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."
58* Chappelle imagines a world where the Internet is a real place.
59-->''(Dave walks by an ObstructiveBureaucrat and a roulette croupier)''\
60'''Bureaucrat''': DEBT CONSOLIDATION!\
61'''Dave''': No.\
62'''Croupier''': Gambling~\
63'''Dave''': No thanks.\
64''(A pop-up appears, repeating the scene)''\
65'''Bureaucrat''': DEBT CONSOLIDATION!\
66'''Dave''': ''(annoyed grumble)''\
67'''Croupier''': Gambling~\
68'''Dave''': ''(more annoyed sounding snarl)''\
69''(Another pop-up appears, repeating the scene)''\
70'''Dave''': ''(shouting over Bureaucrat)'' "DEBT CONSOLIDATION"! "GAMBLING"! [[AnnoyingPopUpAd ENOUGH! ENOUGH WITH THE POP-UPS!]] Dicks!
71** At the end of the skit...
72-->''(The same scene with the ObstructiveBureaucrat and a roulette croupier, this time, Dave punches both of them out as he enters)''\
73'''Dave''': [[ThisIsForEmphasisBitch SPAMBUSTERS, BITCH!]]
74* The "holla atcha bitch!" guy. In one of the HilariousOuttakes, they told the guy to go nuts, and he had everyone on the set rolling.
75* Tyrone Biggums gives a Drug Awareness seminar at an elementary school classroom and becomes the perfect AntiRoleModel for the captive crowd.
76-->'''Teacher:''' I can definitely say he was the absolute worst anti-drug speaker in the history of drugs.
77** ''(after Tyrone had [[ExcrementStatement used the bathroom right in front of the kids]])'' "I thought the worst was over. I was mistaken."
78--> '''Tyrone:''' ''(as the children can only [[BrainBleach look in horror and cover their ears]])'' [[NoodleIncident That, children, was the first time I sucked a dick for crack. But it wouldn't be the last!]]
79* In a later episode, he effortlessly makes it to the finals of ''Series/FearFactor'':
80-->'''Tyrone:''' "I'm gonna tell you something about me, Joe Rogan, that you might not know. I smoke rocks."
81* 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.
82* The Music/LilJon sketches, especially the one with the REAL Lil' Jon.
83** The best part was the real Lil' Jon could do the deep English actor voice too.
84* The scene where everyone in the nightclub dances along to a "new" Music/{{Tupac|Shakur}} joint, with the song making references to things that happened after the real Tupac was murdered (Music/{{Eminem}}, ''VideoGame/GrandTheftAutoSanAndreas'', etc.)
85** On the second verse, Tupac laments, "What can a nigga do/When half the people voted for UsefulNotes/{{George W|Bush}}?" Everyone stops and looks around suspiciously, only to go back to dancing when he explains [[spoiler:he was talking about a guy named George W. Smith... "He ran in '93 out in Oakland/You probably didn't hear about him"]].
86** Tupac starts talking about things that are happening in the club as the record is playing, making it seem like Tupac is somewhere watching and the song is being sung live by a hidden Sakhur! He chastises a patron for having a large stain on her clothes, another patron for not tipping the bartender and him bumping into the DJ booth causing the record to skip, and then Dave Chappelle himself is targeted for dancing with a woman at a club instead of being with his significant other.
87-->'''Tupac''': Dave Chappelle, ''that ain't your wife''! Go home!
88** The song ends thus:
89-->'''DJ''': Tupac, rest in peace.
90-->'''Tupac''': ''Okay, I will!''
91* On the Season 2 blooper reel, Dave's baby starts crying while he and Wayne Brady are filming their sketch:
92-->'''Dave''': Sorry everyone...({{Beat}}) That's ''my'' baby, y'all can't say SHIT!
93* Tron Carter pleads the "[[https://www.youtube.com/watch?v=ERm_WNxGs1U Fif.]]"
94* 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~!"
95* [[http://on.cc.com/QDg4ag "Black Bush"]]. The Iraq War gets satirized as only Dave can. Featuring Creator/JamieFoxx as Black Tony Blair.
96* 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.
97--> '''Sidekick #1''': It's not going double platinum, it's going double uranium!
98--> '''Sidekick #2''': Uranium.
99* Kneehigh Park. The entire thing...
100* The Samuel Jackson Beer sketch, where Dave, as Creator/SamuelLJackson (dressed in a colonial outfit), pitches his namesake beer while [[NoIndoorVoice yelling at the top of his lungs]]:
101--> '''Jackson:''' HOW'S IT TASTE, MOTHERFUCKER?
102--> '''Customer:''' Could you please stop yelling at me?
103--> '''Jackson:''' NO, I CAN'T STOP YELLING, 'CUZ THAT'S HOW I TALK! YOU AIN'T EVER SEEN MY MOVIES?
104* The ''Film/TrainingDay'' parody with Creator/WayneBrady, where he's [[AdamWesting revealed to be]] [[PlayingAgainstType a dangerous sociopath]] -- gunning down a guy with an AK-47, pimping, forcing Dave to smoke Angel Dust, and [[EnemyEatsYourLunch 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).
105** "Is Wayne Brady gonna have to choke a bitch?"
106** The clincher is using his white-friendly appeal to get out a traffic ticket... [[CrossesTheLineTwice only to immediately]] [[NeckSnap snap the cop's neck]], complete with finger-shushing the cop as he lays down his corpse, then screaming WOOOOO! in the car.
107--> '''Brady:''' I make Bryant Gumbel look like Malcolm X, huh, motherfucker?
108--> '''Dave:''' It was Mooney![[note]]In an earlier skit, Paul Mooney, as "Negrodamus", gave this response to someone who asked why white people liked Wayne Brady so much.[[/note]]
109* In the wake of losing control of his show to Brady, Dave calls Big Boi from Music/{{Outkast}} to try and hang out with him. Big Boi responds by [[INeedToGoIronMyDog making lame excuses as to why the two can no longer hang out]], including playing tennis with [[Series/SoulTrain Don Cornelius]]...''on the moon''.
110* 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.
111--> '''Secretary:''' Don't worry. Everyone's a little nervous when they meet Show Business...[[AwesomeEgo except P. Diddy]].
112** Speaking of Diddy, his eccentricity was on full display during the new season of Making da Band: regularly wearing a bathrobe, sending the contestants to run nonsensical errands, treating his bodyguards like furniture... Then [[ItsPronouncedTroPay Dylan]] finally gets his chance in the studio...
113* All three of the "When Keeping It Real Goes Wrong" sketches.
114--> '''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. ''(NoHoldsBarredBeatdown ensues)''
115** The humiliation that Darius regularly endures at his grandmother's house.
116--> '''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...
117--> ''(later)''
118--> '''Narrator:''' He is witness to things that no man should ever have to see.
119--> '''Grandma:''' (''making out with hookup while Darius zones out nearby'') Darius, you big dummy, this ain't no show-and-tell! Take a walk!
120--> '''Hookup:''' Yeah, and get some rubbers!
121--> '''Grandma:''' [[CrossesTheLineTwice And get the big ones.]]
122--> '''Hookup:''' Fuckin' right.
123** The prisoner attempting to start shit with Brenda and the ensuing results.
124--> '''Inmate:''' What's really hood, bitch?
125--> '''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''.
126--> '''Brenda:''' ''(gets in inmate's face)'' Alright bitch, let's settle this ''right now''.
127--> ''(NoHoldsBarredBeatdown on Brenda from multiple inmates ensues)''
128--> '''Narrator:''' The three women were all serving consecutive life sentences. It turned out they kept it realer.
129* Calvin's life getting progressively worse as he works at [=WacArnold's=]. He eventually returns home to his girlfriend, after narrowly missing another man leaving the apartment.
130->''[finding a single black leather glove in the kitchen]'' "Who you fucking? OJ?"

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