Practically from the second “Chappelle’s Show” debuted on Comedy Central in 2003, it was a classic. Take one comedian who clearly didn’t give a fuck, fantastic writing from the likes of Neal Brennan, and a team of players that included Donell Rawlings, Charlie Murphy, Rashida Jones, Billy Burr, Mos Def and many others. Add in musical performances from the best of hip-hop and R&B, and “Chappelle’s Show” became must-see TV for lots of people, with each season becoming more anticipated than the one before it.

Unfortunately (for us, anyway) Chappelle pulled the plug halfway through the filming of Season 3, under pretty shadowy circumstances. He’d just received a mega-million dollar paycheck from Comedy Central. No one knows exactly what happened-was Chappelle under the influence of drugs? Did he crack under the pressure of trying to emulate the success of previous seasons? Were Comedy Central suits trying to take control of his show after giving him the millions? Did Dave have an epiphany regarding the potential socio-political ramifications of his skits? Or did he just game the system for some money and bounce? Regardless of why he split, he left two (and some change) seasons of some of the best sketch comedy of his time.

The Popblerd staff got together and chose the following ten sketches as the best of the “Chappelle’s Show”. It wasn’t easy-there was a point where we actually ripped up the list and started over, but we did it. We also threw a relatively unique wrinkle in there-we didn’t allow the infamous “Charlie Murphy True Hollywood Stories” episode with Rick James to be included, under the impression that a) it’s been overexposed over the years and b) everyone would claim it as their Number One.  Watch and read along. I guarantee you will laugh your ass off.

10) “I Know Black People” Game Show

Know what a loosey is? Knowledgeable about the term “badonkadonk”? Any idea what the words are to that very weird section of the “Good Times” theme song is? Well, Chappelle’s writers couldn’t figure that one out either. However, the first two questions are definitively answered during this “informative” sketch in which Chappelle’s writers grab everyday people from all walks of life (an NYPD officer, an employee at a Chinese food restaurant and an African-American studies professor are just some of the contestants) and quiz them on their knowledge of certain elements of black culture. Aside from the Chinese food restaurant employee, the contestants acquitted themselves pretty well!-Blerd

9) “When Keeping it Real Goes Wrong”

It made the most sense for us to lump the entire series of “Keeping it Real” sketches into one entry, although for my money, the best of these is the one where Brenda gets a wrong-number call from a stranger named Janice, assumes it to be someone messing with her boyfriend, and gets all-the-way gangsta (“Take that, you clap having Jezebel!”). Unfortunately for the window-breaking keeper of all things real, the car she defaces doesn’t belong to Janice, but to her federal agent brother. Prison-related hilarity ensues.-B


Chappelles Show
When Keeping it Real Goes Wrong – Brenda Johnson
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8) “A Day in the Life of Lil Jon”

Back in the early 2000s, it was hard to turn on a radio without hearing the raucous party anthems of Atlanta’s Lil Jon. The dreadlocked and pimp-chaliced rapper was catchy, sure, but he also appeared to be vocabulary-challenged. This was a ball that Dave Chappelle took and ran with all the way to comedy gold. Alternately portraying Lil Jon as a monosyllabic buffoon and an erudite, emotional man with the slightest hint of a British accent, this series of skits was so good that eventually the real Lil Jon got in on the action.-B

7) “The Niggar Family”

The first time that I saw The Niggar Family skit, I really didn’t know what to think about it. Is it funny? Is it offensive? Is it a parody of racial typecasting in mass media? (a la Public Enemy’s “Burn Hollywood Burn” or Spike Lee’s Bamboozled.) Is it a commentary on media stereotyping, or merely a reinforcement of those stereotypes?

I don’t believe I’m the only one left somewhat befuddled. I once showed this in my TV Criticism class a few years ago. Afterwards, a student who had returned to school after raising children declared, “That was the most offensive thing that I’ve ever seen in a classroom.” Indeed, Chappelle’s treatment of race (similar to the ways that Sara Silverman employs race, gender, sexuality, creed, etc.) does nothing if not provoke discussion. Whatever your take may be on this controversial skit, it does get us talking about race – and ultimately, that is its value.-Dr. Gonzo

6) “Black Bush”

Chappelle’s Show proper found its swan song in this, one of Dave’s patented “what if…?” scenarios put to tape; the “what if” in question is, of course, “what if President Bush was black?” Dave avoids easy humor, though, by not imbuing President Bush with silly black stereotypes – instead, the humor is less about the hypothetical leader’s blackisms, and more about the role reversal of a nation of white folks dealing with an outsized caricature of a black man, kinda like a nation of black folks (and, let’s be honest, non-hillbilly white ones) shaking their heads at the antics of a powerful redneck. Chappelle nails the bluster (“You should just sanction me with your army… oh, wait, you don’t HAVE an army!”), the evasion tactics (“M, A, R, S, Mars, bitches”), even recasts Bush’s cabinet as his own garish, dunderheaded entourage. As political and social commentary, “Black Bush” is stellar, and if you’re not laughing before Jamie Foxx shows up as “Black Tony Blair”, bet dollars to WMDs you’ll be won over afterwards.- Drew

5) “Charlie Murphy’s True Hollywood Stories: Prince”

When the Popblerd contributors began compiling lists of the best Chappelle Show sketches, Blerd placed one restriction upon us: “No Rick James, bitch!” True, the Rick James skit is perhaps the most overplayed/overreferenced skit from the show’s run, though it remains a brilliant one nonetheless (though sadly, there is an entire generation whose knowledge of Rick James begins and ends with that skit). At any rate, a favorite skit here at Popblerd was the only other Charlie Murphy’s True Hollywood Stories skit, featuring Prince.

As much as we love him, let’s face it – Prince is ripe for parody. His fashion, his cryptic statements, his mannerisms…. And Chappelle NAILED it. The fog, the humping, the Tootsie Pop, the disinterest/lack of amusement, the miscellaneous groans are certainly manifestations of caricature, but can it be far from the truth? I know that I’ve read stories about Prince’s skills on the on the court – in heels, no less (I believe an associate recounted this in Per Nilsen’s excellent Dance Music Sex Romance). How much creative/comedic license did Murphy take here? Can you really imagine Prince in shorts and sneakers? I also love the idea of Prince only being a master composer, musician and performer whose musical talents are matched only by his mastery of the griddle.-Dr. Gonzo

Chappelles Show
True Hollywood Stories – Prince
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4) “The Mad Real World”

Christian Finnegan plays Chad, a goofy white kid sent to live in an apartment with some uh, very colorful characters in this takeoff on MTV’s hit show “The Real World”. Over the course of his stay, Chad finds himself just a little bit out of his element. Dave Chappelle’s Tron character puts him in a sleeper hold and Chad blacks out. Later on in the episode, his father (who comes to visit with some brownies) finds himself the victim of a stabbing. However, the true comedy gold comes when Chad’s girlfriend Katie visits from Maine and Charlie Murphy’s Tyree character brings his friend “Lysol, fresh out the joint.”-B

Chappelles Show
The Mad Real World – Katie
Buy Chappelle’s Show DVDs Black Comedy True Hollywood Story

3) “Clayton Bigsby-Black White Supremacist”

This was the first controversial “Chappelle’s Show” sketches, and one of the best. Dave plays Clayton Bigsby, an author and textbook white supremacist. There’s only one problem. Bigsby is black. Actually, make that two problems-he’s black AND he’s blind. And none of his friends have the heart to tell him that he’s black. It isn’t until a book signing that Bigsby’s cover is blown, and the results are hilarious (and cause at least one case of spontaneous combustion in the case of Neal Brennan’s character.) This was the point when you realized that Chappelle was capable of making people think in between bouts of laughter, and it was also the first inkling that this show was going to be something special. –B

2) “Wayne Brady Takeover”

It could have been beef. During one of Mr. Paul Mooney’s “Black Nostradamus” sketches, he took an unprovoked shot at entertainer Wayne Brady (“he makes Bryant Gumbel look like Malcolm X”). Somewhere after that sketch, the idea was conceived for the “Wayne Brady Takeover”, which saw the milquetoast-seeming personality taking Dave on a ride that finds Brady randomly shooting people, running a prostitution wet, and getting Dave high on PCP. It was a hilarious change of character for Brady, even though he mentioned after the fact that he didn’t feel totally comfortable doing the sketch.-B

1) “Racial Draft”

One of Chappelle’s most genius high concepts brought to thrilling life by a host of game players (Mos Def, Bill Burr, and the RZA/GZA combo, reprising their entrepreneurial selves from the terrific “Wu-Tang Financial” season-one gag), “Racial Draft” has it all. Chappelle’s best sketches take on all comers, and in this scenario of a sports draft re-envisioned as an event to assign a definitive race to celebs of dubious ethnic makeup, both whites (Chappelle’s recurring – hilarious – take on a stodgy white man blurting out “I’m talking! A WHITE MAN is talking!”) and blacks (Mos Def’s mush-mouthed Rondell, the representative for black folks, indulging in some mischievous antagonism at the white man’s expense) get it in equal dose. But this is softer satire than “Clayton Bigsby” or Dave’s infamous “Pixies” series – the humor here is partially found in the general public’s absurd fixation with everything celebrity (why is it so important to know the exact racial breakdown of Tiger Woods?), and partially in the willingness of people to distance a prominent individual from their core group if they dissent from the party line (Mos’ money-shot punchline about accepting the white acquisition of Condi Rice on the condition that Colin Powell be part of the package), but mostly, it’s gleeful absurdism, as Lenny Kravitz is officially declared Jewish, and, most notably, the Asian delegation snags the entire Wu-Tang clan, in a joke that borders on comic nirvana. Insight, absurdity, and social relevance were many of Chappelle’s touchstones, but he fires on all cylinders with “Racial Draft”.-Drew

Chappelles Show
The Racial Draft
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