Kirk just sent me an IM talking about a line he missed from a Chappelle’s Show sketch, which prompted me to think about what my favorite sketches were. Seemed a perfect time to get the lists back going.
25. The Wrap It Up Box. I’m not even sure this sketch is so funny. But when someone provides me something I can use in my everyday life, it’s worth something. I can’t tell you how many places I’ve been where I wished I had that box.
24. Piss on You. The R. Kelly parody. At times, it’s unnecessarily sophomoric. However, you can’t tell me that you didn’t laugh quite a few times. Which begs the question–have we reached the point where people have totally forgotten that R. Kelly’s got some serious ‘splaining to do? That said, “she be callin’ you Kelly when your name is Tommy” is so funny that I listen to “I’m a Flirt” just to make sure I hear that line. Plus, on the radio, he ain’t wearing a pink mask. The pink mask phase was totally unforgivable.
23. The Three Daves. This is the one where he went through how he’s handled situations differently as he’s gotten older. I can just see myself telling my son “I’m broke, nigga, I’m broke!” And then him telling my wife that I’m cussin’ in the house again.
22. Nelson Mandela Boot Camp. At the risk of sounding diasporically blasphemous, there’s something really funny about Mandela punching kids and smoking their dope. In the jungle, the mighty jungle…
21. Calvin Gets a Job at Wac Arnold’s. Thank you, Dave, for mocking the preposterous notion that working at McDonald’s is a significant contribution to the ghetto. Yeah, that’s uplifting. It may stop a cat from sticking somebody up, but that’s doing as much for uplifting the poor as having a Diet Coke with your Big Mac is good for your health.
20. World Series of Dice. Two words–Leonard Washington. Two more–Ashy Larry.
19. The Niggar Family. Actually, The Wetback Family made it.
18. Law and Order. This is the one where white collar criminals and blue collar criminals are treated inversely to how it goes in real life. “There are so many amendmentssss…I can only choose oneeeee…FIIIIIF!!!”
17. Wu-Tang Financial. “You gotta diversify your bonds, nigga!” The humor, of course, comes from the fact that those dudes surely do know how to manage your money.
16. When Keepin it Real Goes Wrong. All of ’em. The best, to me, was the one where the chick goes bonkers over someone playin’ on her phone. What is it with people and folks playin’ on their phone that drives them over the edge? I got cussed out by a 60 year old man when i was 13 for playin’ on his phone, and I swear, I just dialed a wrong number twice.
15. Trading Spouses. This time, we’re going interracial! Another Leonard Washington classic. But here’s my question–did anyone see on the real “Trading Spouses” when they put the infamous God Warrior–of whatever she calls herself–with some militant dude in Tampa? I missed the second part of the episode, but the first part was the greatest piece of unintentional comedy I’d ever witnessed. Please tell me if you’ve seen it, or if you know when it’s coming back on.
14. Sam Jackson Beer. I’m not a huge Sam Jackson fan. Very good actor, but his choice of role kinda bothers me at times. Dave played on that one flawlessly. “It’ll get you drunk! You’ll be fuckin’ fat girls in no time!” Ahhh, gotta love alcohol. Or not.
13. Come on Be My Baby Tonight. When Dave broke that dude form “The Real World” out and had him sing that silly song as the musical number. Why’s this funny? Nothing like when someone doesn’t realize he’s the joke. He sang his heart out, too.
12. Charlie Murphy Hollywood Stories–Prince. The premise of Prince playing ball is funny enough. “Shoot the J. Shoot it!” is amazing. Pancakes? Well, that couldn’t be invented.
11. Popcopy. First, it was a perfect use of the tragically limited Michael Rappaport. Second, it brought Scarface back out. Third, that’s really what it’s like to go to a copy place. Also, I’ve pretended to be the manager at a job. It’s the best way to get a manager to leave you alone.
11/10. Tyrone Biggums. I just put the main Biggums sketches together, largely because I accidentally made a list of 24 instead of 25 and forgot about “Fear Factor.” Him on “Fear Factor” was pretty good, but nothing beat him talking to a room full of students. Crack addiction ain’t funny, but it can be hard not to laugh at Tyrone. “That children is the first time I…” Oh man, funny. And the demand for cash reminds me of hte time my daddy messed up and paid the cable man some cash to clean out our gutters. Dude was out without us knowing. Shoulda known things were bed when he was begging me for a cigarette five minutes after he got to the house, even though he passed about 5 stores on the way in.
9. Wayne Brady. The shock value of this was enough, but the stuff that happened was perfectly scripted. It also showed just how talented Wayne Brady is, even if you don’t like what he does.
8. Ask a Black Dude. I’m not the biggest Paul Mooney fan. But when you watch the outtakes and realize that, in spite of how serious he sounds on these clips, he’s fighting laughter the whole time, the clips take on a totally different level of humor. Note–this clip should not be so high, but I was running lower than I realized, and I needed to plug something in. Oops. You get what you pay for.
7. Blank. Yeah, I can’t count. Too busy to fix it. Think of this like the center square on a bingo card.
6. Reparations 2003. If you haven’t seen it, I can’t help you. Some think it was embarrassing. I think it was genius. Totally absurd, but I’m okay with that. Goodness, man. This is “Coming to America” funny.
5. Racial Draft. Absolute genius. From black folks trying to give Condoleezza Rice and O.J. away to the Elian Gonzalez bit, this is a fantastic example of subversive racial commentary.
4. Clayton Bigsby, the Black White Supremacist. The beauty of this is how it points out the absurdity of white supremacy. Some folks don’t like it when you talk about white supremacy because the true definition doesn’t adhere to the inflammatory connotation the term has in common parlance, but I can so easily see how someone could not know he was black and still hate black people. Hell, people know they’re black and hate black people all the time. Sketches like this are why I say unequivocally believe Dave’s a genius.
3. Rick James. This is Dave’s defining moment, and it’s classic. The thing I love about this is that, while Rick James’ character is totally absurd, Dave’s portrayal of him is perfectly reserved. It’s a caricature, but not quite. It’s hard to explain what I’m saying, but a great impression comes from subtlety. To me, the little things are what makes this so good.
2. Black Bush. M-A-R-S…
1. Player Haters Ball. First, let it be known I think “Pimps Up, Ho’z Down” is a fantastic documentary. Absolutely fascinating in the same way a great documentary on the Third Reich is fascinating–terrible stuff, but very well done. But this? Man, why hadn’t I heard some of these lines when I was in high school? I would have been the king of rankin’ on fools. “What can I say about your suit that hasn’t been said about Afghanistan? It looks bombed out and depleted.” Genius. And Ice-T coming with “next nigga say something when I’m talkin’s gettin shot, please beleedat.”
In fact, I think I’ll watch that one now.
19 thoughts on “25–Chappelle's Show Sketches”
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it’s funny that you make this list because i was giving one of my boys shit for basing his entire repertoire off chappelle seasons 1/2.
but, in realizing that we’re repeating everything that hasn’t been fresh since 2004 like it’s 2004 chappelle has a new status.
i’ll relate chappelle as the gayle sayers to seinfeld’s emmitt smith. brilliant, cut short too early and will live on as those two seasons of brilliance are quality of HOF induction.
“Oh shit! It’s Wayne Brady!” is all-time legendary status.
Oops. Pow. Surprise.
Ooooooohhhhhhh!!!!!
Lost episodes:
Lil Jon sleeping with Susan Sarandon is damn funny too.
Dave as a werewolf in the Frankenstein skit was acually a great commentary and funny as hell.
Loved the conviction of him saying he never got tired of the Time Haters clip too. Charlie Murphy was priceless.
The sexual consent waiver was a great idea, even if the execution was a bit off.
I am truly a fan of the John Mayer, ?uestlove “White People Can’t Dance” extended skit/musical performance.
The 2Pac “I Wrote This Song A Long Time Ago” was also hilarious.
DJ: “Rest in peace, Tupac.”
Pac: “Okay, I will!”
Great list.
My favorites are probably:
Rick James, WacArnolds, Mad Real World, Reparations, Real Sex Street Interview, Racist TV Animals, Keepin It Real, Black Monsters, World Series of Dice, Black Gallagher, Wu Financial (“This aint ‘Tradin Places’!”).
What made “The Niggar Family” to me was “this racism is killin me inside.” That moment sums up Chappelle’s humor better than any other.
I’m glad he went out on top and didn’t soil his show’s memory (see: Simpsons, In Living Color, etc.)
Bo wrote:
>> It also showed just how talented Wayne Brady is, even if you don’t like what he does.
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So I’ve been watching, but probably for not much longer, the new (borrowed from Australia) show “Thank God You’re Here” show. It is amazing just how UNFUNNY these ” comedians are without a script. I mean some of them literally freeze when having to improv. You’re right, Wayne Brady is a comic genius. If the producers on that show were smart, they’d hire Brady as a permanent performer.
They did have one really good guest on though, Chelsea from “Girls Behaving Badly.” But, she’s suited for improv since GBB improvs quite a bit.
I just saw the racial draft again last night and the Clayton Bigsby bit a few nights before that. The more I see those two skits, the more I laugh. Those two are the tops for me.
Part of what makes the racial draft skit so funny to me, is Mos’ “smoked too many Newports and drank too much Crown Royal , or is it a voice box” – voice as well as his suit (that shit is killer).
First saw that “Piss on You” clip at the taping of the show, and people were almost about to fall out of their chairs. Dave’s genius is that he can go from subversive social commentary to straight up ridiculous junior high humor, and it all works.
People have totally forgotten about the R. Kelly situation. As I’ve said before, I’m so not a fan of dude, but I do acknowledge that he’s talented, I just think he uses his powers more in the service of evil than good.
All over the place, but I also love that “White People Can’t Dance” skit. And Charlie Murphy and Rick James, what can you even say? My favorite part of it all is that it’s all based in fact. Plus, I know chicks who Charlie Murphy was running up on at the time with his classic line, “Hi. I’m Charlie Murphy, Eddie Murphy brother.”
I’d bet $50 that’s still Charlie’s best line. Especially with the trannies.
I took a tour of Paisley Park and when we got to Prince’s dance studio that doubled as his basketball court I lost it. I looked up at the hoops and could only think of pancakes. No one else on the tour seemed to get the joke.
Oh and the Muppet skit with the STDs killed me but maybe only because I love Muppets so much.
Dont forget that And1 mixtape tennis, bowling and baseball. Dave’s physical comedy is SORELY underrated.
The puppets is the greatest…
And that’s why ..i say…fuc* it…!!!!
Man that Fuc* it song is the greatest…
One of the funniest lines ever from the “Player Haters Ball” skit is when Dave says puffy looks like Malcolm X before he converted. It’s so quietly scathing and really, really damning if you know anything about Malcolm.
“Player Haters Ball” takes the cake absolutely.
It made me realize just how much I hate on folks in real life. And how much I enjoy it.
Jarrett..you ain’t never lied, mane..
Especially that line he bust out on Rosie..
“She wear underwear with D*** holes in’em.”..
I was drinking some kool-aid and just spat that out when he said that…classic
“I smell ya light saber.”