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

1. The 64 entries are sketches, not full episodes.

2. What's subjective? Inclusion in the field of 64. Feel free to complain.
3. What's objective? Seedings, which are based on views on comedycentral.com. No complaints allowed.
4. If a long sketch ("Rick James," "The Mad Real World," etc.) is split into multiple clips on comedycentral.com, the views were summed.
5. Recurring segments ("Negrodamus," "Ask a Black Guy," "Lil Jon") are treated as separate entries.
6. 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.
7. End-of-episode musical performances, while extremely important, are not included in this contest. But watch this. Never forget.
8. 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.
9. A win = what I feel is the best sketch. Nothing more, nothing less.
10. If you are disgusted by hyperbole, now would be a good time to leave.
11. 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

1. Redman Potty Fresh

2. Great Moments in Hookup History: Smashley Evans
3. Dude's Night Out
4. Def Comedy Poetry
5. Marijuana PSA Commercial

That's it. ENJOY YOURSELF.

[+] Enlarge

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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