15.) The Three Daves
This was the first real sketch that poked fun at Dave himself (as he very rightfully noted in his routine to the audience before the sketch), and although it wasn't groundbreaking and pretty light, it was really funny. I think it was just short enough to be really effective, not taking too much time for each Dave, and making it just a series of quick-hits. It also brought out a great 'What If?' when Chappelle mentioned that Chris Tucker beat him out for the part in Rush Hour. If that was true, I might really want to see that version of Rush Hour.
Best Line:
- "I'm glad you think Nick Cannon is so God Damn Hilarious, because he just ran off with yo' school clothes money."
14.) Tyrone Biggums Intervention
I wasn't a huge fan of Tyrone Biggums as a Chappelle character, but I much preferred his second sketch to his first, mainly because of how it just grew upon its realistic premise into a complete farce. Chappelle plays Tyrone well throughout, but the sketch is really about the other people's stories. The story of Tyrone taking advantage of the white married couple was so measured that it worked just perfectly. First with Tyrone studying for the test, seemingly cleaning his life, and then spiraling out of control. Of course, the reveal of Tyrone selling the house for a "$450,000 crack party, Come one, Come all!". Just a great satire of a crackhead.
Best Lines:
- "What y'all tell him. Come on, you Benedict Arnolds, what you'll tell him?"
- "It's like the good book said. Let he who is without sin throw-eth the first rock, and I shall smoke it"
13.) Reparations
This was a sketch that probably went a little too long, but packed a lot of great jokes. Plus, it introduced the Tron character, which is probably my favorite recurring Chappelle character. It also introduced the 2nd most famous one-line from the show, with Donell Rawlings, driving hist truck that carries just Newports, yelling "I'm Rich, Bitch!!". The show also introduced Chuck Taylor, Chappelle's great white-face news anchor that would be used quite a few times. This was really early in the show's run, and set the groundwork for a lot of comedy to come.
Best Line
- "Nah, girl. I bought this baby straight cash."
- " Hide the money, ya'll. There's white people around."
12.) Kneehigh Park
Not many elements of Chappelle's Show came from his stand-up work, but this, although altered, might have. Chappelle had a stand-up bit about how adult themed Sesame Street is, and this was basically that version of Sesame Street on crack. It included the best gross-out humor the show ever did. Some of the STD songs fell a little flat (the Herpes one, for instance) but my God was it great. I did seem just a little too crazy to have little kids there, though.
Best Lines:
- "What you don't understand, is I make love to my hand. I don't need you, honey; I beat my dick like it owes me money."
- "Oh, Hello Dave Chappelle. What's it been? Two Months?"
11.) Law & Order
There was a better sketch about the judicial system in this country that is in the Top-10. What hurts Law & Order is other than a few lines, the White side of things fell flat. However, Tron, as a well-regarded crack lord was just brilliant.The depth of that character, and the great performance by his legal team was bueatiful. For anyone that says this showed played on race, I submit this sketch. Chappelle and Co. were so much smarter about comedy in general, as they noticed the hilariousness of the word 'Fif' for Fifth. Him taking the document out of the manila folder saying 'Fif' was just perfect.
Best Lines:
- "Sorry I'm late, but I got caught up in some Punani"
- "When I get out, can I still traffic rocks to the Community?"
- [written] 'FiF'
10.) Charlie Murphy's True Hollywood Stories: Prince
I might be underrating the second iteration of Charlie Murphy's true Hollywood stories, but that is because until the point where they started playing basketball it was underwhelming. However, when the basketball game started it might have become the funniest couple of minutes in the shows run. Just the thought of Prince and the Revolution playing basketball is good enough, but the ridiculous narration and visual gags thrown in made the sketch really brilliant. The little details, like Prince's play being "Darling Picky" right before the whole bit with the fruity pick, or Prince hanging in midair, or them being in their Revolution clothes, or Prince's little tear and nose twitch before the game. All of it came together in a brilliant bit of modern comedy. Of course, though, I would be remiss to not mention the great cap to the whole thing (other than Charlie's speech), which was Prince serving them pancakes. That is as absurdist as it comes, and as funny.
Best Lines
- "He had this other cat, Mickey Free. He was the new cat in Shalamar. When he joined the group, I heard mad cats like Shalamar got this new bitch in the group, she fine as a muthafucker. Mickey Free is not a girl, you understand."
- "Hey, Prince, can we cool this place down"... "Why don't you wash yourself down in the waters of Lake Minnetonka."
- "Shoot the J... SHOOT IT!!"
9.) I Know Black People?!
In the second longest sketh the show ever did (the longest is the one at the top of the list), Chappelle didn't so much force people to be racist, but just poked fun at people's opinions of Black People, and how true many of those opinions were. Apparently those were real random people, not actors, but they all worked so well. That said, a lot of the comedy came from sources that had nothing to do with mining the disparate views of what Black People really are, but Chappelle just being funny, like commenting that "somehow that is right" when he gets a response of 'yes' to 'Is Pimpin' Easy' after a series of nos, or that ridiculous face he makes after singing the end of the Good Times lyric, or his add that, yes, black people will tell a cop "Girl you got a badonkadonk." In the end, it didn't matter that some random guy one, but that we were treated to a really, really fun game show that had memorable contestants, a funny host, and a great idea that presented what could've been a thorny subject in the funniest, most honest way possible.
Best Lines
-"What is a badonkadonk"... "Oh, that's junk in the trunk, what you put your mug on, saddly up and ride.. that's a big.. Ass."
- "I know another actress on Goodtimes was Lenny Kravitz's mother"... "Oh, I'm sorry, that was the Jefferson's, but close."
- "How can they rise up and overcome?"... "Can they overcome?"... "Reparations?"... "That's a complex answer?"... "Staying Alive?"... "Stop cutting each other's throats?"... "Get out and vote?".. "I'm sorry, that is incorrect."
8.) Jury Duty
This might have been the sketch that mixed pointed political and racial opinions with pure comedy better than any other. Listening to Chappelle as the tough potential juror and you started to believe that OJ's bloody glove meant nothing ('I got a couple of bloody gloves on me right now') or that describing Michael Jackson's penis is not all that difficult ('it's gotta head, a shaft, two balls and hair, pressed permed hair... with glitter sprinkled on top), or that it really doesn't make sense that OJ gets arrested two days later when Tupac and Biggie's murders were just never really investigated. Chappelle does at least show that some of his doubts are definitely unreasonable ('they do crazy things with those special effects. That piss coulda been digital) and that maybe our current justice system isn't all that great. The Law & Order sketch was more about race, but Jury Duty was more about the system itself, the idea that one man with his biases could possibly dole out punishment over another man. Oh yeah, it was also hilarious.
Best Lines
- 'Would you let your child sleep with Michael Jackson?'... 'Fuck No!!'
- 'We woulda taken care of OJ the first time he beat my sister. We woulda made Orange Juice outta that nigga'... 'OJ BE DEAD, NIGGA'
- 'Are you aware that Robert Blake is being charged with murder?'... 'Oh yeah. Barretta did that shit.'
- 'How come Biggie and Tupac's murders are out there but you arrest OJ the next day? Nicole Simpson can't rap. I want justice.'
7.) Trading Spouses
This is the first Season 1 sketch so far in the Top-10. There are more to come, but Season 2 dominates the list. That isn't as much a knock on Season 1 as it is a credit to just how incredible Season 2 is. Anyway, back to Trading Spouses. The most incredible part of the sketch was that it was played about a year BEFORE the show aired in the US in its multiple forms (Wife Swap/Trading Spouse). This wasn't that much about the difference in parenting and husbanding styles of Black and White Men, but just differences in general, and mainly sexual ones. The White husband flipping through "Ebony" magazine on the bathroom, while the White Wife gets incredibly horny around the Black Husband. Again, this was shown a good year before Trading Spouses became a show on the US, and like Chappelle's versions of 'Making the Band' and 'Real World' (both still to come) this version of 'Trading Spouses' seems better than the real one.
Best Lines:
- "You betta check your tone, girl. Use your inside voice, before I put you outside."
- "Do you mind if I turn off this R&B Music... I kind of want to hear you breathing. I also feel more comfortable if I pull my penis through this hole."
- "For the first time in my life, I tasted Brown Sugar... and not in my oatmeal."
6.) Making the Band
The most incredible thing about this sketch (and the reality show parody that is yet to come) is that it was still hilarious even if the person had never seen Making the Band. Sure, Diddy himself is a little dated now, but even then, the idea of P. Diddy becoming increasingly lazy, needing to be carried on a sofa and then needing a piggy-back ride. That might be the strangest but funniest joke in Chappelle Show history. The whole sketch was about escalations, really. Other than the Diddy being lazy, was the ridiculous tasks that he would make the group do (get a sugar cookie to buy a set of left-handed golf clubs to getting a picture with a midget holding these balloons to finally getting the breastmilk of a Columbian immigrant) and then his rant about what people were doing instead of working (doing your hair to doing makeup, to chopping onions to doing taxes). Of course, focusing on Diddy leaves out the rest of the sketch, which was largely unmemorable (not a huge fan of the Dylan character) other than Dylan fighting with Wyclef Jean (another great little moment that was funny solely because it was just funny) and Diddy's memorable rant. Overall, though, it perfectly parodied a ridiculous show, a ridiculous character (Diddy) and provided some of the greatest parallel joke structure I've seen in a short sketch.
Best Lines
- [When Fighting Wyclef] 'You're too close man. Too close man.'
- "How yall gonna choke a legend. You can't choke all your problems. It takes hard work. If I had my way, I'd never work. I'd stay home all day, watch Scarface 50 times, eat a Turkey sandwhich and have sex all fucking day. I'd dress up as a clown and surprise kids at schools. Then I'd take a dump in the back of a movie theater, and wait till someone sat in it and hear a squish. That's funny to me. Then I'd paint, read, play violin. I'd climb the mountains and sing the songs I'd like to sing.
- "Playboy? Playboy? You just gonna comb your hair? Sarah? You just gonna talk up all your anytime minutes? Is this anytime? You just gonna sit there and chop onions? This a good time to chop onions? Look at this nigga. You just gonna sit there and do your taxes, Ness? Sit there and crunch numbers? Is that hot? Is that what's going on in the streets?
5.) Frontline: Clayton Bigsby - the Black White Supremacist
Let's get this out in the open, the sketch isn't really as funny as it was groundbreaking. It was the final sketch on the 1st episode of the show (talk about coming out of the gates firing on all cylinders), and it was probably the most pointed sketch in the history of the show. No sketch took such a serious look at racism as this one, but still it didn't mock or satirize racism, but turn the idea on its head about how ingrained it is in our culture. The way his upbringing made him think he was a white is probably not even that far off from what could have been possible. Chappelle proposing that race isn't about color, but about culture, that a culture could make someone who is blind be so against a people of a certain skin color. The other lasting impression of this sketch is Chappelle's easy use of the N-Word in Episode 1. It worked here (even though the word was being used in its most derrogatory form) because Chappelle was saying it, and it continued to work throughout the show's run. The sketch reached its absurdist crescendo in Bigsby's speech in front of KKK members. The speech is notable for being hilarious, which is important, because even in a sketch so pointed in its meaning, Chappelle kept it about the humor and the laughs to the very end.
Best Lines:
- "First of all, they're lazy, good-for-nothing tricksters, crack smoking swindlers, big-butt-having, wide-nose breathing up the white man's air, eating all the chicken; they think they're the best dancers, and they stink."
- "My friend Jasper told me a coon came up to pick up his sister, and he told him 'look here, nigger. If anyone is going to be having sex with my girl, it is going to be me!' "
- "White Power. Colin Powell, Cunnilingus Rice. Cunnilingus Rice sounds like a Mexican Dish, maybe we should send her on a plate to Mexico and let them eat her... White Power."
4.) The Mad Real World
This was one of the first time Chappelle really took to tearing down the hypocrisy and race-baiting present in reality television by turning it totally on its head, and presenting the Real World in, honestly, what is a better version of the actual show. I love how Chappelle can use some of the same characters in different sketches, and his use of Tron (most recently seen as the Richest Man in the World) as the main narrator was just great, as was everyone in the house, including Chad. The sketch actually did little to show why the real version of the Real World is unfair, but instead just poked fun at how a group of black people would act in a similar situation, but added ridiculous elements all around, like Troy adding weed to the smoothies, and Chad's girlfriend immediately turning on Chad and sleeping with Tyree and Lysol (what a great name, by the way). The innocence of Chad was also used well, when he claims that you should never get put into a sleeperhold by a black person because you will wake up the next day bleeding from your anus. The Mad Real World never really followed through on its supposed purpose, but definitely showed just how funny life in an enclosed environment can be,
Best Lines:
- "I did not sleep with Katie"... "Yeah, Tyree, you did sleep with me"... "Correction. I did sleep with Katie.".... "Hey Chad, I slept with Katie too."
- "Katie's got some big ass Tittays"... "Niggas are wilin' "
- "Look at me America. Look how Tron is livin'.. For the Cit-ayy!!"
3.) Black Bush
By far, this was the best political sketch the show ever did. Despite the media's general hatred of the Bush Presidency that was going on during the show's time, Dave never really lampooned the president until this epic sketch. Dave pulled no punch, satirizing every part of the Bush regime, using Black versions of Rumsfeld, the Director of the CIA, and Tony Blair (great, great cameo by Jamie Foxx). The best part of the sketch was that it wasn't even attacking Bush that much, but the lunacy of politics. Black Bush himself admitted that the only reason he wants to go into Iraq is that "that nigga tried to kill my FATHA!!", and that there was oil. He gave a most Bush-like response to the UN, telling them to go get themselves an army. He could have just made the sketch about a black president, and it would have been just as funny, but the subtle digs at Bush and the lack of evidence were just great. But what made the sketch was the part that had nothing to do with Bush, the idea that the war is distracting people from Gay Marraige and the Moon. M-A-R-S, MARS, Bitches. Red Rocks. The final sketch in the real era of the Chappelle Show was a home run.
Best Lines:
- "What about people who say you're only interested in the Middle East for oil?"... "What? Huh, Oil? Who said something about oil, bitch. You cooking? Oil?"
- "Kofi Annan, you think I'm gonna take orders from an African? You might speak sixteen langauges, but you're gonna need 'em when you're out in Times Square selling fake hats. I know Gucci when I see one, nigga, I'm rich"
- "Can't be distracted about what's going on in the War, what's going on in the economy. I got that shit under control. Let's focus on Space, nigga. The United States of Space. Write this down. M-A-R-S, Mars, bitches. That's where we're going. Red Rocks!"
2.) The Playa Haters Ball
With the exception of the sketch still to come, no sketch used non-Chappelle cast members better than the Playa Hater's Ball, which was about as perfect as a sketch can be. It started off well with the hilarious screen of HBO doing documentaries on pimps, hos, mark-ass tricks and trick-ass marks and everything else, and now doing one on haters. The best part of the sketch was without any set-up, all four of the main haters (Buc Nasty, Beautiful, Pit Bull and Silky) were really well established. Patrice O'Neal (RIP) was just brilliant as Pit Bull, as well Donnell and Charlie (his first real use on the show). What really made the sketch go, though, was the fact that this was a little glimpse into the life of a comedian when they are with their pals. It really seemed like four comedian buddies (Murphy, Rawlings, O'Neal and Chappelle) just took turns making up lines and shitting on each other. Much of the sketch seemed improvised, and a lot of it was (what gives it away is after Chappelle's slam on Rosie that "she wears underwear with dickholes in 'em" everyone breaks and they leave it in). The whole sketch seemed like a lot of fun, and for a show that was usually so exacting, it was great to see a sketch with absolutely no social commentary, and just insult after hilarious, biting insult.
Best Lines:
- "The so called Beautiful, why don't you click your heels together three times, and go back to Africa. And as for you, Boss Hogg. Very insulting what you said about my coat. It's made from your momma's pubic hair."
- [On Rosie O'Donnell during the photo-flip] "Now that's one bitch I wouldn't want to fight. She's got underwears with dickholes in 'em"
- "Beautiful on the weekends does stunts for Little Richard in Gay Movies. First off, I would like to thank God ALmighty for giving evrybody so much, and me so little. 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 no one but you. Now if you'll excuse me I have to go home, and put some water in Buc Nasty's Momma's dish."
1.) Charlie Murphy's True Hollywood Stories: Rick James
What else, really. It might be overhyped. It might be the mainstream choice. That said, sometimes, the object of the mainstream's affection is well deserved, and that is the case here. If you want to create a perfect sketch, just follow what Chappelle and company did here. They perfectly satirized a memorable, crazy character. They created (or if we believe Charlie, used) ridiculous situations, but ones that fit the characters. Make every scene have great background jokes. Everything just worked perfectly in this long-form piece, from the narration, to the use of the real Rick James, to adding little details like the Security Guard being cross-eyed, or the Unity ring. Everything was just perfect. It was basically the whole episode, and even then it seems really tight and short, flowing perfectly in essentially just four scenes (Studio 54, Eddie's apartment, Rick's hotel room, China Club) all comically basic, it never, ever felt like it was dragging. That said, the best part of the sketch was probably the use of the two narrators in Charlie and Rick. Charlie is just a great storyteller (though that was better used in the Prince sketch), while Rick was just great. The "Cocaine's a Hell of a Drug" line got funnier and funnier each time until it became the funniest thing I've ever heard. His rant about not stomping dirt on the couch than immediately contradicting himself was a great touch. Using the real Rick almost humanized the Chappelle Rick, and really gave the sketch a kind, almost appreciable, base. The best part of the sketch is that I haven't even mentioned the infamous 'I'm Rick James, Bitch!' line, and even if that was never spoken, this sketch still would be number 1.
Best Lines:
- "Welcome to the China Club... A Chonga Chang Chang, a Chonga Chung Chang."
- "Fuck Yo Couch, Nigga. I've been kicked out of better homes than this. I'll be back, you black muthafucka. Wide-nose-having muthafucka. They shoulda never given you niggas money, you don't know how to appreciate shit."
- "It's a celebration, bitches. Show Charlie Murphy your titties.... The Milk's Gone Bad, Charlie"
