I‘m not sure if it’s the best show, or the funniest show, or the smartest show, or even the bravest show, but I do know that Chappelle’s Show is hands down, without a close second, the most important show of my life. Since its debut on January 22, 2003, it became one of the few television shows that I watched every week, in real time, the night it aired. There are two reasons for this: (1) It was revolutionary, and (2) it was unacceptable to show up to high school the next day without knowing all the material from the previous night’s episode. Social suicide, the kids still call it. And since the show went off the air in 2006, my weekly intake has only slightly decreased.

There’s nothing I’d call myself an “expert” in, but for all intents and purposes, I have a PhD in “Ashy Larry” from the accredited institution of higher learning known as David Khari Webber Chappelle. For that reason, I feel confident in my abilities to carry this out in the most professionally passionate way possible.

The 11 Rules

The 64 entries are sketches, not full episodes. What’s subjective? Inclusion in the field of 64. Feel free to complain. What’s objective? Seedings, which are based on views on comedycentral.com. No complaints allowed. If a long sketch (“Rick James,” “The Mad Real World,” etc.) is split into multiple clips on comedycentral.com, the views were summed. Recurring segments (“Negrodamus,” “Ask a Black Guy,” “Lil Jon”) are treated as separate entries. Sketches that had multiple parts airing at different points of the same episode (“Piss on You,” “Reparations 2003,” “Pixies,” etc.) are treated as one sketch, and the views of their separate parts were summed. End-of-episode musical performances, while extremely important, are not included in this contest. But watch this. Never forget. There is a noticeable bias, by way of views, toward newer clips (Season 3), which is unfortunate because that’s Chappelle’s worst. But know that that doesn’t really matter, because seedings are almost irrelevant. A win = what I feel is the best sketch. Nothing more, nothing less. If you are disgusted by hyperbole, now would be a good time to leave. If you are not well versed in Chappelle, stop now. This isn’t amateur hour. Consider this bracketology’s FINAL BOSS.

The Five That Just Missed the Cut

Redman Potty Fresh Great Moments in Hookup History: Smashley Evans Dude’s Night Out Def Comedy Poetry Marijuana PSA Commercial

That’s it. ENJOY YOURSELF.

Round of 64

Silky Johnson Region

Prince (1) vs. Ask a Black Dude: Size Matters/They’ll Take Your Show (16)

While pretty much anything going up against “Game, Blouses” will lose (this “Ask a Black Dude” segment included), this isn’t as much of a blowout as one would think. This “Ask a Black Dude” sketch, from Season 1, essentially has Paul Mooney (out of his Negrodamus garb) eerily (and hilariously) prophetic about the way Chappelle’s Show ultimately ended (“I get to talkin’ some mess on your show, they’ll take your show”). This seemed to be rattling around in Dave’s head when he turned down $50 million instead of pushing out a full third season. So yeah, an important sketch but there were no grapes, pancakes, or Micki Free, so it loses. ONWARD, REVOLUTION.

Jedi Sex Scandal (8) vs. Don’t Pitch Me (9)

Had I not gone through and recently watched every episode, I would have forgotten about the “Jedi Sex Scandal” sketch. As a rule of thumb in this bracket (there are a few, where I simply can’t deny my biases), if Chuck Taylor is around, it gets a leg up, mainly because he looks just like David Gregory. Anyway, there are few things funnier than watching Yoda say, “Over, this interview is.” Until the next scene when Yoda says, “Ooh, about it tell me,” vocally transforming into a flamboyant black man. Just fantastic. Against Yoda is “Don’t Pitch Me,” the sketch in which we all learned to always tell Arsenio how good the cheese is, or ELSE. Both sketches have their weak moments as they push along, so at the end it comes down to the classic matchup of Yoda vs. Arsenio. What a beautiful world we live in where that can happen. Anyway, Arsenio wins, easily, if for no other reason than those twists he was wearing in 2004.

Kneehigh Park (5) vs. Dave’s Educated Guess Line (12)

“Kneehigh Park” is equal parts disgusting and genius. It’s disgusting because the entire sketch is about puppets (and Q-Tip) teaching children about venereal diseases. It’s genius because it allowed Charlie Murphy to do the voice of Stinky — the puppet that lived in a “fucking trash can” (sound familiar?) — curse at children, and sing one of the most beautiful songs ever, titled “That’s Why I Say Fuck It” (I’m listening to it right now). Against “Kneehigh Park” is one of the most beautifully racist sketches he’s ever done. It’s classic Dave, because he toes the line of prejudice by making fun of everyone. Oh, and that outfit. I’ve been looking for a two-piece purple dashiki set since the day this aired. I love the hotline, and in my ideal world it actually exists, but it’s narrowly edged out by Kneehigh Park. Narrowly. Had Snoop not voiced the puppet known as “Dangle,” it might have gone the other way. Oh, and had that little girl not called Dave Chappelle “Chris Rock.” That too.

Piss on You (4) vs. Mitsubishi Commercial (13)

This is one of the more lopsided matchups of the entire tournament. While the Mitsubishi commercial is pretty awesome (and shockingly dated; WHERE YOU AT, DIRTY VEGAS?), the reason it’s important is because it’s the first sketch ever. Not a bad way to start the most culturally important show of the decade. Unfortunately, it’s up against “Piss on You,” which, excuse my French, “drip, drip, drips” all over the competition. It’s just too good.

Fear Factor (6) vs. The Wrap-It-Up Box (11)

The “Fear Factor” episode gave us a top-10 Chappelle’s Show quote:

“I’m-a tell you something about me, Joe Rogan, that you might not know. I smoke rocks.” —Tyrone Biggums

I love the Wrap-It-Up Box, especially when the girl is going on and on and Dave just replies with “Word,” but Tyrone Biggums is an institution and this might be his magnum opus. Oh, Tyrone also says, “My feet are strong” while walking across the hot coals, which is a quote I utter on a daily basis. Oh yeah, Tyreeta is also in this sketch. Yeah, this competition is over.

Wayne Brady (3) vs. Give Up the Show (14)

This is a fitting matchup, because “Give Up the Show,” is the setup for the Wayne Brady sketch. I almost lumped these together, but they really need to be treated like two separate entities. Again, like the “Ask a Black Dude” sketch, Dave predicted what probably ended up happening, with him giving up the show, people thinking he’d lost it, and then being cast out by the likes of Big Boi and Nick Cannon. But again, no matter how prophetic this was, it can’t overtake one of the funniest sketches. Ever. Get comfortable, Wayne, you aren’t going anywhere.

Keeping It Real: Vernon Franklin (7) vs. Popcopy (10)

I have to admit, I liked every “When Keeping It Real Goes Wrong” sketch, but I didn’t love them. Funny, just not my favorite. Anyway, the one that always stood apart was the one with Dave as Vernon Franklin, the precocious young man who loses his cool in the boardroom and goes on one of the more real tirades I’ve ever seen. I can’t lie, there’s not really much that tops a rant that goes from “five on the black-hand side” to “soft-shoe and juggle watermelon” to “allow me to reintroduce myself, my name is Hov” to “thuglife” to a series of DMX barks to “WU-TANG.” Sorry, Popcopy. I love you, but you never had a chance.

WU-TANG.

Tupac Is Still Alive (2) vs. Love Contract (15)

You have to give Chappelle credit for taking one of the most tired jokes ever, Tupac still being alive, and turning it into a hilarious segment. One of the highlights of Season 3 might be when “Tupac” goes through the long-winded story of explaining that by “George W.” he meant “George W. Smith … from city council … he ran in ’93 … out in Oakland … you probably didn’t hear about him.” It’s just too good. That moment alone is one of the reasons I went from almost excluding Season 3 from the bracket to having everything be fair game. Going against the sketch that gave us “It might be DOO-DOO” is “The Love Contract.” Earlier I mentioned one of my biases being sketches that feature Chuck Taylor. Bias no. 2: sketches involving Rashida Jones. Why lie: Her chariot awaits whenever she decides to call me back. Anyway, Rashida with disheveled hair + the line “the love contract, because you’d hate to catch a beef for something you know you didn’t do” + the fact that I always forget the second part of this sketch involves the even funnier “Confidentiality Agreement” + “KOBE” makes this a near-perfect, short-but-sweet sketch. Yes, Tupac is funny, but it comes up short. 15-2 upset, baby. RASHIDA ON TO THE NEXT ROUND.

Buck Nasty Region

Mad Real World (1) vs. Mooney on Movies (16)

So yes. “Mad Real World” wins. Obviously. But before I move on, I have to talk about one of my favorite moments from the series, which takes place in “Mooney on Movies.” When they go into the second film, Barbershop, one of the ladies gives a nice description of the film. As she’s talking, Mooney is shaking his head, about to erupt. And when she finishes, Mooney simply says, “You know it’s just a front; they really sell drugs at barbershops.” And that’s it. Just unreal. But yeah, Tron, Tyree, and Katie easily on to the next round.

Trading Spouses (8) vs. Black Gallagher (9)

This is a weird matchup, because when I think about Black Gallagher, I immediately think about the outtakes on the Season 2 DVD, which couldn’t be funnier. The actual sketch is hilarious, too, but just not as funny as the footage left behind. Coupling that with the fact that every single thing in “Trading Spouses” is executed perfectly makes “Black Gallagher”‘s road to the Round of 32 an uphill battle. From Todd cooking parsnips to Leonard saying “Who the fuck is Renee Zell-wedge-er” to Leonard dropping his new son off in the hood and saying “G-g-g-good-bye” to Leonard explaining how white people wash themselves, all while a cigarette delicately dangles from his mouth, this couldn’t be any better. A surprisingly easy win for T-Mart and the gang.

Lil Jon vs. Lil Jon (5) vs. Slow Motion (12)

Sorry, “Slow Motion” sketch, but the last 30 seconds of the phone call between Lil Jon and Lil Jon might trump everything.

(Bold = Lil Jon, Italics = Chappelle as Lil Jon.)

“That was Oprah, she’s having our baby. Yeaaaahhhhh. I can’t hear you, my cell phone’s breaking up. I can’t hear you, it sounds like your phone is breaking up. What? What? What? What? What? What? OK, Yeah, Yeaaah, Yeah, Yeaaah, What? What? OK, OK, Yeah. Affirmative, huh? Roger? Yeah. What? Melting down. Ahhhh. BYE, NIGGA.”

So yeah, that’s how you move on.

Racial Draft (4) vs. Tyrone Biggums: Red Balls (13)

There was a lot of pressure going into Season 2 of Chappelle’s Show. But the first episode did not disappoint, due in large part to the “Racial Draft.” Dave as Tiger, Mos Def in that red suit, Condoleezza given away by blacks, and the creepy Wu-Tang part at the end only begin to scratch the surface of how good this sketch is. On the other side is “Red Balls.” I’ve never really stopped thinking about the part when Tyrone steals the lady’s radio, runs away, then comes back and says, “FYI, people still do steal radios, how do you think I got this suit,” goes into a Harlem shake, and then screams “RED BALLS GOT ME, AHHHH!” It’s a fantastic sketch, but it can’t really compete with the then–Secretary of State being given away by her race. So rude. So good.

Tyrone Biggums: Drug Awareness Class (6) vs. And1 Sports (11)

I originally thought that this was a no-brainer in favor of Tyrone and the completely inappropriate drug talk he gave to an elementary school class. I always remembered the “And1 Sports” bit being funny, but not that funny. Then I watched it again and realized how wrong I was. The names of the different guys, Ronny “Fielder’s Choice” Banks, Kenny “Baseline” Sims, and Reggie “Gutterballs” Bryant make me smile, and having insane crowd reactions for baseball, tennis, and bowling is just too funny. Oh, and one other thing: Let the record show that the idea of playing defense in bowling is priceless. Few things top that. So I’m going to call this a huge upset, with the often-overlooked Season 1 sketch knocking out heavyweight Tyrone Biggums. Don’t worry, though, Biggums Stans, he has plenty of classics left.

The Niggar Family (3) vs. Ribs (14)

Dave Chappelle should be given an American Sociological Association Lifetime Achievement Award for inventing “The Niggar Family.” That’s all I have to say about that for now. Sorry, “Ribs,” but Timmy Niggar does NOT play around.

Dave Gets Oprah Pregnant (7) vs. Negrodamus: Wayne Brady (10)

The way Dave reacted when he found out he got Oprah pregnant is one of the rudest and most accurate stories he ever told on the show. Getting Oprah pregnant would 100 percent bring out the worst in any good-natured human. I promise. Anyway, the sketch is awesome, especially the fact that The Jeffersons theme song is playing in the background. Oh, and the fact that he sings karaoke with a crew of Asian people with fighter pilot goggles on. Going against this sketch is one of the Negrodamus sketches. Not only does this sketch have one of the dumbest, funniest jokes I’ve ever heard (“Arnold Schwarzenegger will divorce his wife and marry Shirley Temple Black and she will be Mrs. Shirley Temple Black Nigga”), but it immediately goes into the joke that sets up perhaps the best Chappelle’s Show sketch ever (“White people love Wayne Brady because he makes Bryant Gumbel look like Malcolm X”). While it pains me to see Oprah’s pregnancy not make it to the next round, there’s no way to knock out this Negrodamus sketch this early.

The Playa Hater’s Ball (2) vs. Great NY Boobs (15)

Before a single person even appears on the screen for “The Playa Hater’s Ball,” its opening credits give it a bye into at least the Sweet 16. The text:

“HBO, the greatest network of our time, has brought you compelling documentaries about pimps, ho’s, players, johns, tricks, marks, mark-ass tricks, trick-ass marks, skeezers, skanks, skig-scags, and scallywhops … ”

It’s so good, I’ve almost forgotten what “Great NY Boobs” was even about. HATE HATE HATE.

Pitbull Region

Rick James (1) vs. Lil Jon Interview (16)

The Theresa Roddy interview is one of the better Lil Jon sketches, especially the highly emotional monologue about black youth, but no. Just no.

Calvin Got a Job/WacArnold’s (8) vs. Life Like a Video Game (9)

“Ew, nigga, you smell like French fries” and “It’s a thin line between fries and shakes” are two of my favorite Chappelle lines, both from the WacArnold’s sketch. Like so many Chappelle sketches, this one is very much a social commentary, but in addition to that, there’s no denying how hysterical this segment is. This is especially true once Calvin makes it back to his house and starts verbally threatening the mother of his child that if she keeps acting up, she will not get the rib sandwich that’s coming out the following Tuesday. Going against “WacArnold’s” is the sketch “Life Like a Video Game,” in which Chappelle makes fun of Grand Theft Auto. It’s not a very complicated sketch, but it is very well done, from the different camera angles to the way Dave walks to the way he switches around his guns until he’s satisfied with his killing machine. The impersonations are spot-on almost to the point of being cute. Sadly, cute always loses to generational poverty and urban blight, so “WacArnold’s” advances.

Wu-Tang Financial (5) vs. I Know Black People (12)

This is unfortunate. If put in different sections of the bracket, both of these sketches could easily be Sweet 16–bound. Unfortunately, one has to go and it’s really not that hard of a decision. I love everything about “Wu-Tang Financial.” I’m still waiting for the day when I walk into Bank of America and the first employee that sees me grabs my hand and says, “You need to diversify yo bonds, nigga.” I don’t care who they are or what they look like, I will embrace them and start crying tears of joy. Anyway, as much as I love Wu-Tang Financial, there’s no way it can touch “I Know Black People.” The responses to “What is a loosie?” alone would probably send it to the next round. Or if not just that, “loosie” + Chappelle playing air-bass while singing the Good Times theme. Either way, “I Know Black People” marches forward. Sorry, The GZA. Sorry, The RZA.

The Time Haters (4) vs. History’s Greatest Wars (13)

These two great segments, one about the Playa Haters going back in time and the other about the turf war between the 19th Street Gangsters and the River Terrace Crew, are pretty equal in number of laughs. The great thing about both is that each has a standout passage, and determining which is better seems like the only appropriate way to determine which advances. In “The Time Haters,” Silky Johnson explains the word “Honky” to those living in the 1800s by saying:

“‘Honky’ is a racial epithet used for white people. It was made popular by a man named George Jefferson in the 1970s. You see, he and his wife, Weezy, owned a dry-cleaning business, so they moved on up to the east side, to a deluxe apartment in the sky. They finally got a piece of the pie. Convoluted story, I’ll admit, but the point is this … that in the future, all black people will be FREE.”

And then he goes on to hilariously, repeatedly shoot a slavemaster. In the “History’s Greatest Wars” segment, General Cornrow Wallace (played by Mos Def) sends a note from jail that says:

On top of that being illiteracy at its most comical, it’s additionally great because what Mos Def reads and what the letter actually says don’t match up (listen and read at the same time; it’s awesome). Anyway, a tough battle, but “History’s Greatest Wars” is beefing its way to the next round. Ppprrrrr.

Tyrone Intervention (6) vs. Real Movies: Deep Impact (11)

The Tyrone Biggums intervention sketch is important, because it gave us two outstanding crack references, the “Five o’Clock Free Crack Giveaway” and “Come to Tyrone’s $450,000 Crack Party.” Classic crack references. On the other end is the Deep Impact spoof, with Chappelle as a presidential Morgan Freeman, telling the world all the secrets he knows, since Earth is about to end by way of a meteor. The only thing better than exposing AIDS cures, cloning, magic bullets, magic, and Bibble is the wig and faux-facial hair Chappelle decided to don to impersonate Morgan Freeman. This matchup is a tough one, but Dave as Morgan Freeman as pre-Obama has to move on. I’m not upset about that one bit.

Black Bush (3) vs. Three Daves (14)

I love watching “Three Daves,” because I plan on releasing a similar video when I turn 30. I’ve already written the script for 18-year old Rembert and, for better or for worse, it’s not that different from 18-year-old Dave. My script for 24 will be finished soon after finishing this bracket. As for 30, I really hope that I, too, am screaming at my kid because he’s more interested in Diggy Simmons than in his father. As much as I have applied this sketch to my real life, it’s going up against one of the better sketches to watch in present day, seeing that we have one of those black president things now. If the outtakes to “Black Bush” were in this bracket, it would win in a landslide, but the aired sketch, unlike “Black Gallagher,” is still extremely above average. “Black Bush” advances and, not to look ahead, but we’ve got a second-round black-on-black president bloodbath on our hands. CAN’T WAIT.

Jury Selection (7) vs. Mandela Boot Camp (10)

“Mandela Boot Camp” is phenomenal, not only because even Dave knows it’s a horrible impression of Nelson Mandela, but also because the premise of Nelson Mandela having a boot camp that takes in rough kids from the Sally Jesse Raphael show is second only to defense in bowling in terms of absurdly genius concepts. Before the seedings worked themselves out, I really wanted this sketch to make its way into the second or third round, just because it’s so silly. Unfortunately, it ran into the sketch with the single greatest description of Michael Jackson’s “alleged” penis in the history of Michael Jackson “alleged” penis descriptions: “There’s a head, a shaft, some balls, hair — maybe press-permed hair — with glitter sprinkled on it.” “Jury Selection” advances on the strength of that quote alone, which is saying something, given that there’s still R. Kelly, O.J., and Robert Blake to be discussed.

Cribs (2) vs. Nat King Cole (15)

Even though I’ve mentioned my bias against Season 3, there’s no denying the mastery that is the Chappelle “Cribs” sketch. Whether it is The Real World, Making the Band, or Cribs, Dave truly knew how to take a reality show and accurately mock every ridiculous aspect of it. Between the initial quote of “Come on in, you broke motherfuckers,” his reversible white panda/bald eagle fur, and a chicken bone chandelier, he nails it. So good. Too good, actually, with regard to its competition, the “Nat King Cole” sketch. Yes, watching Dave as an inappropriate Nat King Cole is always fun, but it’s just no match for watching Dave open his freezer, pull out a Tyrannosaurus Rex egg, and say, “Y’all wanna eat some dinosaur, nigga? Let’s try it out.”

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Beautiful Region

Pixies (1) vs. Two-Minute Special (16)

Oh, the “Pixies” sketch. If you’re a fan of the show, it’s uncomfortable to watch this sketch, not because it’s so racially in-your-face, but because it’s widely considered to be the sketch that drove Chappelle away from the show. I happen to think the sketch has some hilarious parts, but I can see why a man would question his larger goals of helping the greater racial dialogue after promoting a sketch like “Pixies.” Going against this sketch is “Two-Minute Special.” This is one of those Chappelle sketches that is so simple, it’s hard to believe no one had ever thought of it. Of course someone should make fun of that overexaggerated period of time when someone is making his way to the stage. It’s hilarious. From the very slow walk to the touching of the soundboard (which consists of adjusting absolutely nothing) to the long chug of water, he hits on every point of absurdity. I love “Two-Minute Special,” and even if the “Pixies” sketches weren’t the beginning of the end, I’d still have them falling in this matchup. Buh-bye, no. 1 seed. And good riddance.

Making the Band (8) vs. Roots Bloopers (9)

Fans of the “Making the Band” sketch get understandably caught up in all things “Dylan, Dylan, Dylan, Dylan, Dylan.” While that line is hilarious, it isn’t even the funniest thing Chappelle as Dylan said in the sketch. I invite anyone to tell me something funnier than Dylan saying:

“I already had about five labels call me today, 50 labels called me total, and there’s only six.”

That pile of mathematical nonsense gets me every time. It’s so dumb and perfect. Anyway, obviously Diddy, Chopper, Babs, and the rest advance. The fake bloopers from fake Roots are great, but Diddy’s wet, shiny, Chapstick-covered lips are even greater.

Reparations 2003 (5) vs. A Gay World (12)

Yes, there are a few funny segments in the “A Gay World” sketch, but the handful of seconds during which we, the viewers, are privileged to see that man sashay across the grass with his lawnmower and his booty shorts is amazing.

AMAZING.

I could also go into the segment about the gay chapter of the KKK, but it’s a moot point, seeing as this sketch is going against “Reparations 2003.” To say this sketch is important is a gross understatement. In addition to being hilarious, it introduced the world to (1) Chuck Taylor, (2) TRON, and (3) the sound bite used for the ending credits, “I’m Rich, BEEATCH [honk honk].” That’s about a third of the things I love about Chappelle’s Show, all stemming from one sketch. Anyway, this grossly undervalued sketch wins in a landslide, and I feel bad for any other sketch in its path.

Samuel Jackson Beer (4) vs. Zapped (13)

I mean —

“Good muthafucking choice, muthafucka. Samuel Jackson, made painstakingly by me, Samuel L. Jackson. It’ll get you drunk. You’ll be fucking fat girls in no time. You might even fight a nigga or two. MM-MMM, BITCH. [Breath.] How’s it taste, muthafucka? Huh? [Rudely interrupted and asked to stop yelling.] No, I can’t stop yelling, ’cause that’s how I talk. You ain’t never seen my movies? JUICE? That was a good one. Deep Blue Sea? They ate me. A FUCKING SHARK ATE ME. DRANK, BITCH. Jurassic Park? Samuel Jackson. It’s my beer. YES, THEY DESERVE TO DIE, AND I HOPE THEY BURN IN HELL.”

I love a good sketch about a misguided prank/hidden camera show, but I neither want to die nor burn in hell, so Samuel L. moves on.

White People Dancing (6) vs. Make a Wish (11)

Ladies and gentlemen, the worst rap verse in American history:

“I’ll battle any sex or any race. You beating me is like Billy Crystal playing Scarface. I can’t see it, blind to the eyes. Came up in your face. OOPS POW SURPRISE, ohhhhh.”

It’s so bad, it’s beautiful. That’s all I’m saying about this. Bye, “Make a Wish.” Ohhhhhhhh.

World Series of Dice (3) vs. Law & Order (14)

This is the hardest matchup of the first round, hands down. Both of these sketches are legendary. One has Ashy Larry and the other has some remarkably comical animal cruelty. Don’t take me as someone who enjoys watching bad things happen to animals — quite the contrary, but in the first scene of “Jury Selection” when the police blast through the house, roll a grenade toward the golden retriever, and then shoot the dog in the head, I can’t help but die laughing. IT’S FUNNY, I’M SORRY. Not only is this flipping of the script of the justice system (in the eyes of Dave) extremely clever (especially when they show the “jury of your peers”), but it gave the world another classic Chappelle quote: “I plead the fif.”

Just fantastic.

Equally fantastic is the “World Series of Dice.” Yes, there are other characters than Ashy Larry, but for chrissakes there’s not much funnier than Donnell Rawlings covered in chalk, squandering his family’s money away in a dice game in the middle of the Marcy projects. And it only gets better when he introduces himself by “Ashy Larry, Marcy Projects, Marcy Son, What.” It’s too good. I can’t believe one of these sketches has to get knocked out this early, but that’s how it works, and that sketch is “The World Series of Dice.” Ashy Larry, Grits N’ Gravy, and Leonard Washington are wonderful, but Tron holding up his sign is simply too much.

Howard Dean (7) vs. Fisticuffs (10)

If the “Fisticuffs” shtick was two hours long, I would still be amused and still laugh when he complains about the velvet in the headphones, when he can’t hear the beat, and when the beat drops how he wasn’t prepared for the beat to drop. For some people with weird senses of humor, this is one of the funniest comedy sketches. Ever. I happen to be one of those people. Going against it is the “Howard Dean” sketch. My two favorite parts about this sketch are the fact that they left in the part when he directly addresses Tom Harkin, and then at the end, after six or seven “byaaaahs,” he drops the mic. Always a great move. So yeah, solid sketch, but no way it outperforms Fisticuffs. Not even close … Tom Harkin.

Clayton Bigsby: Black White Supremacist (2) vs. Roca Pads (15)

The Clayton Bigsby sketch is so good, not even a Rashida Jones cameo in “Roca Pads” could save it. I will always love Dame Dash for doing this sketch, but this is Clayton Bigsby we’re talking about. Even Dame would understand.

Round of 32

Silky Johnson Region

Prince (1) vs. Don’t Pitch Me (9)

So, in addition to Arsenio complaining about the cheese, you also have Dave rapping as a half-man/half-sheep. Very great. Oh, and a shirtless Anthony Anderson rubbing himself down with rose petals, à la American Beauty. Also great. The problem, however, is that only one of these sketches has the line “Why don’t you purify yourself in the waters of Lake Minnetonka?” And that would be Prince. So, yeah — bye, Arsenio.

Kneehigh Park (5) vs. Piss on You (4)

It’s weirdly fitting that these two get matched up with one another. Both are highly inappropriate, both have singing, both involve sexual deviancy, and both are funny in the sense that you don’t want to laugh, because you shouldn’t be laughing, which ultimately makes you laugh even more. The major difference between these two sketches, however, is that whereas a few jokes fall flat in “Kneehigh Park,” “Piss on You” (and the accompanying remix) never falters. Every single lyric is golden. The song is so good, I once had it on MP3. What we have to remember is that before we all knew it would turn into “Piss on You,” we sat and watched for the first 20 seconds as Chappelle changed the lyrics to a familiar track, “Feelin’ on Your Booty.” There was no way to really expect the song to take a turn for “Take me to your special place, close your eyes, show me your face. I’m gonna piss on it.” That was truly a moment and set the stage for two more minutes of increasingly insane lyrics. The sketch was rightfully a phenomenon, and for that reason, in addition to the fact that it’s just funnier, it advances to the Sweet 16.

Tyrone Biggums: Fear Factor (6) vs. Wayne Brady (3)

If this was a bracket of “most shocking Chappelle’s Show moments,” a no-brainer Final Four entry would be the moment Donnell Rawlings screams, “Oh shit, it’s Wayne Brady, son!” and proceeds to get shot repeatedly by a AK-47–wielding, “RIVERSIDE, MOTHERFUCKER!”–yelling Wayne Brady. Anyone who says they figured that was the direction the episode was going is a liar. As soon as that happened, you knew you were in for one of the wilder comedy sketches in the show’s history. And it didn’t disappoint. No disrespect to Fear Factor, Joe Rogan, and Mr. and Mrs. Biggums, but you ran up against a big dog. Just know there’s no shame in a loss to Wayne Brady, son.

Keeping It Real: Vernon Franklin (7) vs. The Love Contract (15)

I won’t lie, Rashida will definitely help a sketch get through the first round, but after that her powers are rendered almost useless. Almost. “The Love Contract” is a great sketch, but not a Sweet 16 sketch. It’s one of the better fake product advertisements Chappelle ever ran, but it’s hard to justify it as one of the 16 best sketches, especially when it’s going against Dave as Vernon Franklin, boardroom flipper-outer. I’ve got to be honest, this is a pretty easy win for “When Keeping It Real Goes Wrong,” and I’m happy to see it still alive. The more Wu-Tang–related sketches in the Sweet 16, the better.

Buck Nasty Region

Mad Real World (1) vs. Trading Spouses (8)

Not to be too rude, but while this is a fun matchup of spoofs of television shows, deciding the winner in this contest is very, very easy. One of these sketches is funny and the other has a character who gets his girlfriend stolen and then his dad gets stabbed. One of these sketches is clever and the other has a character named Lysol. I love Leonard Washington, but the Tron + Tyree two-hit combo is not something to be taken lightly. “Mad Real World” was one of the first sketches to really send Chappelle’s Show into the cultural stratosphere, and it is easily deserving of a spot in the Sweet 16. Easily.

Lil Jon vs. Lil Jon (5) vs. Racial Draft (4)

Both of these sketches deserve to go on to the next round (this is about to be a recurring problem). The problem is that Dave has more than 16 classic sketches, so from here on out it’s about to get unfairly hard. The Lil Jon sketches were some of the most popular on Chappelle, with “Lil Jon vs. Lil Jon” serving as the “this joke has officially come full circle” sketch. Fully understanding that and appreciating what this sketch means to the show, it’s still going up again “Racial Draft.” People still reference the idea of racial drafts in present day, less for reasons of obtaining people from other races, but more by way of snide comments about giving away celebrity X for being a complete embarrassment. The idea is genius, and it’s carried out in a pretty flawless manner. So yeah, no real discussion on who is advancing. I wouldn’t have predicted a Lil Jon–less Sweet 16, but these things happen.

And1 Sports (11) vs. Niggar Family (3)

So here’s the thing. Watching Dave mock the And1 basketball phenomenon makes you sit back and think, Dave might be a comedic genius. Watching “Niggar Family” unfold before your eyes, however, makes you gasp in amazement, while thinking, Dave might just be a genius. So yeah, that’s really all I have to say about that. Shout-out to Hot Sauce.

Negrodamus: Wayne Brady (10) vs. The Playa Hater’s Ball (2)

In the first round, I didn’t even get to the actual “Playa Hater’s Ball” sketch because the intro alone was enough for a win. Not much is different for this matchup, with a single joke from “The Playa Hater’s Ball” completely TKO-ing “Negrodamus.” Silky Johnson:

“And of course the so-called Beautiful, why don’t you click your heels together three times and go back to Africa.”

Be offended all you want, blacks, but that’s about the funniest joke I’ve ever heard. The haters Silky, Beautiful, Buck Nasty, and Pitbull (also the namesakes for the four bracket regions) are going to have a hard time losing in this tournament, I’m just throwing it out there. AND I HAVEN’T EVEN BROUGHT UP THE ANNUAL PHOTO FLIP YET. Goodness gracious.

Pitbull Region

Rick James (1) vs. Calvin Got a Job/WacArnold’s (8)

I’ve been talking a lot about Dave Chappelle and perhaps not enough about his co-stars. Season 1 introduced the world to Charlie Murphy, but with Season 2’s “Charlie Murphy’s True Hollywood Stories,” Eddie’s younger brother finally became a household name. Yes, the star of the first installment of this series is Dave Chappelle as Rick James, but the story doesn’t reach the cult-classic level it has without the storytelling capabilities of Charlie Murphy. Yes, Rick’s antics are beautiful, but some of Charlie’s quotes are even funnier than Rick’s. Example 1 of 50:

“Things escalated to the point where, you know, my man got too familiar and I ended up having to whip his ass, man, you know, ’cause, you know, he would step across the line. Habitually. He was a habitual line-stepper.”

English has never sounded so violently sweet. Bye, WacArnold’s.

I Know Black People (12) vs. History’s Greatest Wars (13)

I’ve found that many people who claim to know a lot about Chappelle don’t really remember “History’s Greatest Wars.” It’s phenomenal, and because I always felt as if it was my secret sketch, I’ve long had a special relationship with it. Going into this bracket, the sketch was going to be my sleeper to pull upset after upset. Well, seeding-wise, it pulled one in the first round, but unfortunately it has just run into “I Know Black People.” I have no problem admitting my biases, but I can’t allow myself to just be flat-out wrong. “I Know Black People” is a classic. The part where “Get out and vote” is the only wrong answer to “How can black people rise up and overcome?” is so messed up, but, like most things on Chappelle, it’s kind of true. There are tons of other quotables, but the entire episode is a buildup to that line. So good. I know “History’s Greatest Wars” lost, but watch this again. Ppppprrrrr.

Deep Impact (11) vs. Black Bush (3)

This contest, overdramatized earlier to be a matchup of two black presidential sketches, is just a complete blowout. “Black Bush” obviously wins. Easily. I’m not even going to waste time explaining why.

Jury Selection (7) vs. Cribs (2)

“Cribs” is great, but “Jury Selection” just has too many great lines. His take on O.J. is amazing:

“I’d have to be real confused, ’cause nobody in my family would beef with O.J. like that. And we would’ve killed O.J. after the first time he beat my sister. We’d have whooped his ass, we’d have made real orange juice out of that nigga.”

As for one of his many explanations of Michael Jackson’s innocence, he throws out one of the more purposefully confusing quotes of the series.

(Lawyer = Bold, Chappelle = Italics)

“He has been accused of this more than once. Some people say that cucumbers taste better pickled. What? Huh? What? Huh?”

Awesome. If you don’t think about that line once a week, you aren’t living right. Anyway, it’s just a wonderful sketch, and there are few things I find funnier than people admitting the irrational biases for their own race. That move is always a winner. So yeah, good run, “Cribs,” but c u l8r.

SEASON 3 IS GONE. REJOICE. HARK! THE HERALD ANGELS SING.

Beautiful Region

Two-Minute Special (16) vs. Making the Band (8)

The “Two-Minute Special” sketch is hot off the ultimate upset, trying to continue its ’98 Bryce Drew/Valparaiso Cinderella run with a second-round win as well. Unfortunately, dreams do not come true since that just isn’t happening. I don’t even really feel right going deep into “Making the Band” until it has some real competition, all disrespect intended. So yeah, just know that.

Reparations 2003 (5) vs. Samuel Jackson Beer (4)

This might seem unfair, but one of the main things “Reparations 2003” has on a sketch like “Samuel Jackson Beer” is purely the length of sketch. The Samuel L. sketch is barely a minute long, whereas the two parts of “Reparations 2003” are about seven minutes total. It wouldn’t matter, though, were not all seven minutes hilarious. Even within the first minute, with the black lady outside the store fanning herself with money and upon seeing a white reporter, yelling, “Hide the money, y’all, there’s poor people around … wit ‘cha broke ass,” you know it’s going to be a great sketch. I love wearing a pirate hat and yelling like Sam as much as the next guy, but the reparations sketch goes beyond funny, whereas “Samuel Jackson Beer” never really makes it out of that stage. So yeah, this is the end of the road, Samuel. Also, as an aside, if “Reparations 2003” wins the bracket, the sketch comes true. FINGERS CROSSED.

White People Dancing (6) vs. Law & Order (14)

I’m shocked so few people have watched the Chappelle “Law & Order” episode. It coming in as a 14 seed is a travesty, but that’s further proof that seeds don’t matter. “White People Dancing” has a lot going in its favor (Questlove, a barbershop, pre–David Duke John Mayer, crazy white people, and Spanish gibberish over a megaphone). That’s a ton. But it is missing something — something that unfortunately not every sketch can have. That something? TRON. I’m sorry, but Tron is easily the funniest recurring character on Chappelle’s Show. He’s such a jovial drug dealer, with impeccable style and a fantastic tendency to run his mouth to no end. It’s no surprise: With “Law & Order” advancing (which it is), Tron has a role in three of the Sweet 16 sketches (including “Mad Real World” and “Reparations 2003”). His character just makes sketches better, especially when he graces a sketch with lines like “When I get out, can I still traffic rocks to the community?” and “You’re right, sellin’ rocks would be wrong. [Laughter.] Jail’s the shit!” He’s the 2 Chainz of Chappelle’s Show, which is the highest compliment known to man.

Clayton Bigsby: Black White Supremacist (2) vs. Fisticuffs (10)

On the very first episode of Chappelle’s Show, Dave got away with having a black, racist, blind man say:

“My message is simple. Niggers, Jews, homosexuals, Mexicans, Arabs, and all kinds of different chanks STANK and I hate ’em.”

So yeah, just keep that in mind. This contest just got a little too real for “turn my headphones up.”

Sweet 16

Note: Just looking at what’s left, 11 are first-ballot Hall of Famers, another two are extremely close, two more are underrated classics, and one had an easy draw and snuck in. Also, everything in the Buck Nasty region could be in the Final Four. That’s enough, I’ve said too much.

Silky Johnson Region

Prince (1) vs. Piss on You (4)

At this point in the tournament, using “funny” as the sole indicator of advancement is no longer appropriate. Every sketch that has made it this far is, by definition, hysterical (even the one that snuck in). Because the majority of the remaining sketches are multidimensional, some of the non-funny aspects of the sketches are important with regard to advancing to the Elite Eight and beyond. The Prince sketch is a perfect example of this. Yes, it’s funny, but the story that Charlie Murphy tells is simply impeccable. They are branded as “True Hollywood Stories,” but it’s impossible to truly know what to believe as fact and what is exaggeration. Did the Revolution really not change clothes for basketball? Can Prince really hoop like that? Did Prince really end the game with a dunk, levitate, and then float back to the ground? These questions may never be answered, but the story is so good it ultimately doesn’t really matter. “Piss on You” is a musical, comedic tour de force that really doesn’t let up until the last note is over (there’s actually a tank labeled “R. Kelly’s Doo Doo Butter“). It’s comedy gold, but that’s it. At least that’s how it feels, compared to Prince. Did he really make them pancakes? Is Micki Free really not a girl? I could go on with these questions, and I probably will in the next round, because the sketch is advancing. GOOD.

Wayne Brady (3) vs. Keeping It Real (7)

Not to put a sketch on blast or anything, but one of these two sketches was the one I was alluding to when I mentioned “had an easy draw and snuck in.” This sketch is an above-average piece of comedy and has rightfully defeated its initial competitors, but the end is near — in about 50 words, to be exact. The “Wayne Brady” sketch stemmed from Dave making fun of Wayne in a “Negrodamus” sketch, and the next thing you know Wayne’s on the show, mocking the very notion that he’s not tough. It’s egoless, it shows a real sense of humor, and the end result was a classic. Of course Wayne and Dave’s intense “blacktors” field trip makes it to the Elite Eight.

Buck Nasty Region

Mad Real World (1) vs. Racial Draft (4)

As previously mentioned, this region has four classic sketches that are worthy of advancing to the Final Four. Even as I write this, I’m not sure which way this should go. The one thing I can’t shake, however, is that while “Racial Draft” is completely unique with regard to Chappelle sketches, “Mad Real World” is one of a few sketches in which Dave and the crew make fun of a reality show. While it was the first, looking back on all of them, it’s not the best. If I want to see Chappelle make fun of a reality show, I’m finding the “Making the Band” sketch, without hesitation. There wasn’t really anything like “Racial Draft” before it and there hasn’t successfully been anything like it since. While “Mad Real World” had a template — an already ridiculous one — to work from, “Racial Draft” came just from the evil-genius minds of Dave and co-creator Neal Brennan and attacked the issue of multiculturalism head-on. It has to advance.

Niggar Family (3) vs. Playa Hater’s Ball (2)

It has taken months to finish this project, less because of the amount of content to digest, and more because of fear. I’ve reached different points, at different occasions, where I couldn’t make a decision, prompting me to put it on the shelf for a series of weeks. This matchup was one of those points.

“Playa Hater’s Ball” is, without exception, the most quotable sketch in Chappelle’s Show history. For the duration of the sketch, it doesn’t calm down one bit, just hitting you with line after line. I’ll never get over the fact that, during the photo flip, Dave said that Diddy looked “like Malcolm X before he converted to Islam.” And the decision to use the take when they all explode in laughter after the Rosie O’Donnell line “she wears underwear with dick-holes in them” was just genius. “Niggar Family” has fewer memorable lines, but what it lacks in quips it makes up for by being one of the smartest comedy sketches. Ever. He gave a white family the last name “Niggar.” When the mom officially breaks the seal by commenting on a family picture, saying, “She’s got those Niggar lips,” it’s cripplingly uncomfortable and hilarious. Watching and hearing white people say “Niggar” over and over again, in the masterful context that Chappelle set up, is still jarring, even when you’ve seen the sketch hundreds of times and know when it’s coming. And then there’s Chappelle’s milkman character. Between “I know not to get between a Niggar and their pork — might get my fingers bit,” “I know how forgetful you Niggars are about paying your bills,” and “All right, peace, Niggar,” there’s just no way this doesn’t make it to the next round. It seems weird to knock out “Playa Hater’s Ball,” given that I’ve quoted it twice today, but this is the end of the road.

Pitbull Region

Rick James (1) vs. I Know Black People (12)

You’ve got to applaud “I Know Black People” for making it this far. When speculating what the Sweet 16 might look like, I hadn’t immediately thought of the sketch, but it definitely deserves to be among the likes of “Piss on You,” “The Racial Draft,” and “Making the Band.” “Rick James,” though? Questionable. They are both very long sketches, so that’s something they have in common, but the long amount of time with Rick is noticeably more hysterical than with Dave and his contestants. Yes, the barber is the greatest game show contestant not named John Carpenter, but there’s no Charlie Murphy, no China Club, no UNITY rings, and no licking of faces. So yeah, “Rick James” advances. Easily.

Black Bush (3) vs. Jury Selection (7)

Why does “Black Bush” dominate “Jury Selection”? Answer: “Black Bush” spent 46 seconds talking about “yellow cake.” That’s just phenomenal. Yes, Chappelle as Bush is great, and yes, Mos Def as “black head of the CIA” is just ridiculous, but few things top Anthony Berry (as “Some Black Guy”) and his two lines: “cradle of fucking civilization” and “pray to God you don’t drop that shit.” Chappelle talking about O.J. and MJ is great, but it’s got nothing on yellow cake, or the other seven classic minutes. The idea of Obama watching this sketch and smiling while eating some White House yellow cake is the greatest mental image that currently exists.

Beautiful Region

Making the Band (8) vs. Reparations 2003 (5)

While it is hard to imitate any real person, it’s even more difficult to pull it off when the person is currently relevant. The parody of Rick James worked for many reasons, but one was that he was such a legendarily absurd character from the past, Dave could essentially do anything and people would buy into it. The idea of Rick making girls flash them upon arrival to the club didn’t even seem absurd, because you just always heard tales of Rick as a wild guy. But when it’s someone like Diddy, someone whom everyone knows everything about, one can’t be as liberal in just making things up. Luckily for Dave, sticking to the script with Mr. Combs still provided him with a sizable quantity of material. And the extent to which he nailed it makes it really the only Diddy impersonation that matters. The juicy lips, the earpiece in, the absurd demands, the tendency to not walk without assistance, the Harlem shake tick, the catchphrases, and then this speech.

“If I had my way, I’d never work. I’d just stay home all day, watch Scarface 50 times, eat a turkey sandwich, and have sex all fucking day. Then I’d dress up like a clown and surprise kids at schools. Then I’d take a dump in the back of a movie theater, and just wait until somebody sat in it. Hear it squish. That’s funny to me. Then I’d paint, and read, and play violin. I’d climb the mountains, and sing the songs that I like to sing. But I don’t got that kind of time.”

Just excellent. I love the breast milk out of you, “Reparations 2003,” but your time is done. Diddy said “squish.” That’s amazing.

Clayton Bigsby (2) vs. Law & Order (14)

Sometimes Chappelle did things that I still can’t believe made it on television. Three of those things are Clayton Bigsby’s books, titled N—– Stain, I Smell N—–, and N—– Book. That’s incredible, and it took place in the first minute of the sketch. Following the listing of those books (and Dump Truck — we can’t forget about the first book), there’s eight more minutes of “I also can’t believe that made it on television.” Everything about the “Law & Order” sketch is great, especially the smart premise of switching the roles and races within the court system, but it’s not on the same level as the black white supremacist. I can’t believe Dave picked those names for those books. First episode. Amazing.

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Elite Eight

Note: Prince, Wayne, Rick, Bush, Clayton, Diddy, a draft, and some Niggars. That’s it. There are no more weak sketches. I think this is the best thing ever.

Silky Johnson Region

Prince (1) vs. Wayne Brady (3)

This is like having to pick your favorite mom when you have two moms. It’s rude, there’s no real right answer, and it’s just not fair. Also, there’s no going back on this decision. Once you pick one, the other knows how you feel and it’ll never really be the same. This is, hands down, the most difficult of the four matchups that lead to the Final Four. On multiple occasions, I’ve penciled in both “Prince” and “Wayne Brady” as the Silky Johnson representative in the Final Four, panicked, and then erased the winner. I’m stalling so hard right now, not because I haven’t made up my mind, but because I can’t believe I’m about to knock out “Prince.”

So yeah, “Prince” loses.

“Wayne Brady” wins.

One reason and one reason only: shock factor. They’re equally great sketches, but the stage had already been set for “Prince” (the first Charlie Murphy’s True Hollywood Story, “Rick James,” aired the previous week), but there wasn’t a single warning for “Wayne Brady.” Wayne was on the show because Dave had made fun of him in a previous episode, so the absolute last person you were expecting to make an episode-long cameo was Wayne Brady. But that’s why it’s one of the best: the context that surrounds the entire absurd episode. And on top of all that, clean-cut Wayne has guns, drugs, and hookers. I’m not saying that the Prince sketch was predictable by any stretch of the imagination, but some of the newness that existed with Rick James was lost by the time Prince came around. This is all I have to say about this, because if I keep rambling, I’m going to change my mind. So yeah, blouses out, Brady in. Someone’s going to off me for this one.

At least it won’t be Wayne.

Buck Nasty Region

Racial Draft (4) vs. Niggar Family (3)

These are two of the smartest, simplest Chappelle sketches out there. They are simple because each takes something the public is extremely familiar with (a draft, a family) and, with a single tweak, completely turns it on its head. It doesn’t take a paragraph to describe each sketch, it only takes a sentence. “It’s like a normal draft, but the teams are races” vs. “It’s a white family, but their last name is Niggar.” That’s it. Like the previous matchup, what a win comes down to isn’t “which is funnier” but an external characteristic of the sketch. That external characteristic is longevity, and there’s no denying the continuing significance of the idea of a racial draft some eight years later. The fact that that sketch has taken on a life of its own beyond Chappelle is pretty remarkable, but none of it would be true had the sketch not been spot-on in every aspect. From the newscasters, to each race’s representative, to the picks, to the side deals, it’s hard to imagine a real-life racial draft that didn’t play out just like Dave predicted. Bye, Niggars. Thank you for all you do.

Pitbull Region

Rick James (1) vs. Black Bush (3)

Here’s an old-school SAT analogy:

“Hey Ya” : OutKast :: Rick James : Dave Chappelle

OutKast will never be as popular as they were when “Hey Ya” came out, and it elevated them to another level, but it’s also this weird curse that they’ll never really escape. This is exactly the way Dave Chappelle and his show are with the Rick James sketch. Without the sketch, it is a considerably less well-known show, but the mania surrounding the sketch at a certain point began to dwarf the rest of the show and the man behind it. It’s the gift and the curse of extreme popularity. Dave mentions this in his stand-up special For What It’s Worth when he speaks on being at Disney World with his kids and having people in the park come up to him and say “I’m Rick James, bitch” and him responding with “You mind not calling me a bitch in front of my kids? Time out, motherfucker, can we take a day off?” Even with some of the negatives that have come with the “Rick James” sketch, there’s no denying its legacy, its complete domination of our popular culture, and its status as the most widely known Chappelle’s Show sketch. If “Black Bush” goes against a few of the other Elite Eight sketches, it probably makes its way into the Final Four, but not when it goes against “Rick James.” “Black Bush” is classic, but “Rick James” is forever.

Beautiful Region

Clayton Bigsby (2) vs. Making the Band (8)

Seven of the Elite Eight are sketches from Season 2. Seems lopsided, but the truth of the matter is that the second season is much, much better than the very good first season. The remaining one, from Season 1, happens to be in this very matchup, with “Clayton Bigsby: Black White Supremacist” going up against Diddy and Da Band. While “Making the Band” would be a pretty solid representative of the inaugural season, purely on number of laughs alone, it doesn’t have a defining moment like the point at which Clayton Bigsby snatches off his KKK hood, exposing his black face to the white-supremacist crowd. The buildup to that ends up being more exciting than the repeated plots of “Making the Band” that essentially were band fights, Diddy shuts down studio, Diddy makes them do something ridiculous, Diddy opens studio back up, band fights, etc. “Making the Band” is an exceptional sketch, but it just can’t compete with the in-your-face final sketch of the first episode of Chappelle’s Show.

Final Four

Note: No more regions. No more seeds. Just the GOATs.

Rick James vs. Wayne Brady

All of these lines happen in less than three minutes.

“Nice place, nigga.” — Dave as Rick

“Fuck yo couch, nigga.” — Dave as Rick

“Buy another one, you rich motherfucker.” — Dave as Rick

“See, this is long before Wesley Snipes. Back then, we were the blackest niggas on the planet, according to Rick James.” — Charlie Murphy

“See, I never just did things just to do them. Come on, what am I gonna do? Just all of a sudden jump up and grind my feet on somebody’s couch like it’s something to do? Come on. I got a little more sense then that … Yeah, I remember grinding my feet on Eddie’s couch.” — Rick James

“See, I never just did things just to do them. Come on, what am I gonna do? Just all of a sudden jump up and grind my feet on somebody’s couch like it’s something to do? Come on. I got a little more sense then that … Yeah, I remember grinding my feet on Eddie’s couch.” — Rick James, rewound

“AHHHH, you darkness, you black midnight evil motherfucker. Black magic, darkness, you raw, darkness, you fucking delirious motherfucker.” — Dave as Rick

“You are cold as ice.” — Dave as Rick

“His legs was like linguini.” — Charlie Murphy

“I’ve been kicked out of better homes than this. They never shoulda gave you niggas money. What I’ma do about my legs, Charlie Murphy?” — Dave as Rick

The level of condensed hilarity in this scene, one in which we see Dave (as Rick) stomp into Eddie Murphy’s living room, stomp his muddy boots on Eddie’s white couch, and then proceed to get his legs beaten, is unparalleled. And that’s just one of the many scenes within the Rick James sketch. So it has to win, right? Right?

Weirdly enough, no. Here’s why.

The “Wayne Brady” sketch is fantastical, but at its core it’s a complete self-takedown of the two main characters, Wayne Brady and Dave Chappelle. Coming into the sketch, Dave is the crude black guy who will say anything, push the limits, and generally live his life without fear of repercussions, while Wayne is the safe black guy whom people’s grandmothers love and probably hasn’t committed a vile act a day in his life. That is the reputation that each built for himself, and this was reinforced by Dave making fun of Wayne in an earlier episode. They were polar opposites of the black-actor spectrum, seemingly having no overlap when it came to their common craft of joke-telling.

Then eight minutes go by and, at the end of the sketch, they have forced you to imagine a world where everything you assumed was wrong, with Wayne not as safe as you thought and Dave not the tough rule-breaker you’ve grown to believe him to be. And then, stepping outside of the sketch, it hits you that what they’ve shown by collaborating and sharing a stage is that they aren’t polar opposites of the black-comedian spectrum. It’s a spectrum, and they’re showing its fluidity.

But it goes even further than that. This sketch is probably the one time in the three-ish seasons of Chappelle’s Show that Dave so clearly played second fiddle to another actor. Dave has a tendency to dominate sketches, through no fault of his own, but simply because he’s usually the funniest man on screen. The “Wayne Brady” sketch trucks along not because of Chappelle, but because of Wayne Brady. Dave’s role is to simply be a scaredy-cat and react to the craziness that Wayne gets them into. Yes, it’s all very funny and that’s the initial attraction to the sketch, but it’s also a great moment in comedic collaboration that no one could have seen coming. Comedians make a living off having whipping boys. Very rarely do they then work with those people, and then even more rarely do they give them top billing. It’s a beautifully egoless moment for both men.

Yes, Rick James is the character that Chappelle will always be known for, and it marvelously did wonders to introduce a new audience to the legend that was Rick James (airing only a few months before his unfortunate death, rightfully giving the man one last breath of stardom). The Rick James sketch is also the most consistently funny sketch, impressive considering its length. But when I think about Dave Chappelle, the writer, the comedian, and the guy who was accidentally (and purposefully) revolutionary with the content he put on the air, the Wayne Brady sketch is one of the biggest tricks he ever had under his sleeve.

So that’s it. Wayne and Dave are championship-bound, Rick is gone, and I think I’m finally OK with that decision. And if it means anything to you, know that it took two months to make that pick, and then another month to write some sort of rationale. Again, let me move on before I change my mind.

Clayton Bigsby vs. The Racial Draft

Dave Chappelle really knew how to kick off a television season with some controversy. Two of his most overtly racially charged sketches, “Frontline: Clayton Bigsby” and “Racial Draft,” were the final sketches of the first episodes of Season 1 and 2, respectively. Both set the tone for the rest of the season, letting the viewer know there were no limits to what could be discussed if the subject matter was attacked in an intelligently humorous way.

“Racial Draft” makes that clear from the outset, by using very stereotypical caricatures from each race serving as the representatives. And then this exchange between Chappelle and his two white co-commentators took place:

White Commentator 1: Believe it or not, the blacks have won the first pick.

Dave: Wow, that’s the first lottery a black person’s won in a long time.

White Commentator 2: Yes, and they’ll probably still complain.

[White commentator laughter.]

Dave: Man, fuck you.

Love that. And then there’s the time Tiger Woods got drafted by the blacks and then lost all his endorsements, prompting Dave to say:

“Tough break, nigga. There’s always FUBU.”

I also love that. And then there’s the Colin Powell–Condoleezza Rice–Eminem–O.J. deal between the blacks and the whites. Rude and fantastic.

It’s all very racial, filled with generalizations, and funny if you have a sense of humor about these things. Compared to the black white supremacist and the story of Clayton Bigsby, however, it comes off like an Upper East Side prep school assembly on post-racial America. While “Racial Draft” aims to make you laugh while thinking about race, the black white supremacist sketch was put on this earth to make all passersby feel uncomfortable. Uncomfortable to watch it alone, uncomfortable to watch it in mixed company, uncomfortable to laugh, and uncomfortable to then talk about. There’s nothing quite like it.

The first 15 seconds:

And then, soon after, your fears (or hopes) come true as you learn that that was an old white guy saying this. Before even meeting Clayton, or learning that there would be a black character whose blindness allowed him to be a white supremacist, we’re greeted with these two slides, which let us know this is about to be some controversial goodness.

This matchup isn’t as hard as the other Final Four matchup, because it’s clear that one completely eviscerates 99.999 percent of comedic racial commentaries ever put on television. Yes, “Racial Draft” was extremely important because it let us know that Season 1 wasn’t a fluke and Dave still had it, but the black white supremacist showed us from the starting block that this show would be more than simply a variety sketch show. Leave that 2004 simple stuff for Nick and Jessica.

CHAMPIONSHIP

Clayton Bigsby vs. Wayne Brady

The last 22 seconds of “Clayton Bigsby”:

Thanks for playing, everyone.

There was never any question of what would win this bracket. “Clayton Bigsby” is Dave’s Illmatic. You get the feeling he’d been playing around with the idea of a black white supremacist for years, so it should be no surprise that it came first. The Nas analogy is accurate, because it’s not as if he peaked and then slowly declined or faded into obscurity (I didn’t say “Clayton Bigsby is his Introducing the Hardline According to Terence Trent D’Arby“), but his greatest contribution to his craft and the culture and the social commentary just so happened to occur at the very beginning.

You have to be extremely creative and talented to successfully mock racism. The mistake that most make when trying to mix satire with racial commentary is that it either comes off too cautious or it lands on the other side of the spectrum and simply comes off as racist in its own right. Dave found the balance throughout this show’s run, but his first attempt was his riskiest and his best.

Many of the other popular sketches became such classics because they were so quotable. Between “Playa Hater’s Ball,” “Rick James,” “Prince,” and “Black Bush,” I can think of 50 lines that my friends of all races and I have traded over the years. “Clayton Bigsby,” not so much. It’s so purposefully inflammatory, it almost has to exist in its original form, on-screen, digested by those who appreciate its genius through repeat viewings instead of simply trading quotables until you’ve narrated the entire sketch. Almost.

Today marks the 10th anniversary of the airing of this sketch, but this still isn’t a world where “I’m in no way, shape, or form involved in any niggerdom” is universally acceptable to be said by anyone, to anyone. In a way, I think that’s a net positive, that this sketch didn’t get the Rick James, “Fuck yo couch, nigga” mass-appeal treatment — and has been taken slightly more cautiously by the public, even as the sketch has many points at which laughing and participating is by all means encouraged. This is true because, at its core, this is a serious sketch. Dave didn’t put on a full KKK white robe and hood just to make people laugh. The humor was present to cut the tension from an all-out assault on racism. Who knows, but if my hunch is at all correct, then bless this sketch for existing. At the time, we all needed it, and we still do.

This has been great. Thank you for existing, Chappelle’s Show. Every generation, group of friends, and individual needs that cultural event that they can always relate to their formative years. I know I speak for many when I say I’m extremely lucky and thankful that Chappelle is mine, and not Love & Hip Hop: Atlanta. Thank you so much.