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In tackling this week’s episodes, I feared I made a mistake. A few weeks back, I offered up a trio of episodes instead of the usual two in order to end our trip through season two on the 13th and final installment. I worried that I should have done that threefer this week, since the 11th episode is a “greatest misses” romp that never airs a full sketch. Luckily, diving into the “misses” episode yields an interesting look at a show in flux, while the 10th episode offers up one of the most disturbing puppet-based pieces of comedy in modern times. It’s a compelling set of episodes that shows the series operating at full power as well as the way in which the Chappelle’s Show creative engine was already burning out.


“Episode 2-10” (season 2, episode 10; originally aired 3/24/2004)

“Making The Band”: As with any good sketch show, Chappelle’s Show travels in sketches timeless and topical. There’s nothing wrong with that approach in the moment, but it makes certain sketches less cutting after time has passed. Given the half-life of reality TV show popularity, the Sean “P. Diddy” Combs-curated show that inspires this parody feels like part of the Mesozoic Pop Culture Era. While it’s easy enough to gather what Chappelle is mocking here, there’s just not the immediate frame of reference to make this one of the show’s all-time best.


All that said, the relatively low ceiling on this sketch’s ultimate rate of success doesn’t stop this piece from having a series of laugh-out-loud moments. I don’t remember if Combs himself came off lazy on Making The Band, but Chappelle’s jokes about his inability to perform any type of physical activity escalate to incredibly surreal heights. From falling asleep in his assistant’s arms after eating a sugar cookie to using his dreadlocks like stirrups, Chappelle-as-Diddy is a model of ennui-based success. Here’s a man so bored that he has to send his protégés to northern New Jersey to take a picture of a balloon-wielding midget, or to secure breast milk from a Cambodian immigrant.

The protégés themselves don’t really register, which makes any time spent away from Diddy rather dull. It’s clear from the audience reaction that Chappelle’s impersonation of the disillusioned Combs struck a chord. But even if I vaguely remember Diddy’s increasingly elaborate scavenger hunts, I don’t remember a single thing about a single performer on this show. (Then again, I couldn’t tell you half of the winners of American Idol, either.) That’s in part due to my general apathy toward reality competitions and the sheer number of shows that traffic in these types of contents. The sketch works best when creating rules of its own, rather than aping the original product.


“Dude’s Night Out”: This feels more like a proto-“Digital Short” than perhaps anything else on the show so far. The repetitious use of the cheesy graphic for Schlipp’s Beer, the hard-rock music, and the almost ADD-like quality of the editing add up to one of the early attempts by the boys from The Lonely Island to bring their particular sensibility to Saturday Night Live. But just like many of those early attempts, this one is a bit of a failure. Documenting men behaving badly is fine, but there’s little sense of any story behind this particular descent into Hell.

Do sketches need stories to be successful? It’s something we’ve discussed a lot during our look at Chappelle’s Show. Many believe it’s irrelevant to a particular piece’s comedic success rate. And there’s some merit to that philosophy. Not every joke needs a large backstory in order to deploy laughter. But Chappelle’s Show excels at taking a premise from a smart start to a logical conclusion, often going through a series of narrative steps that feel coherent within the world its created. “Dude’s Night Out” is just a series of jokes involving the same four guys, none of whom have any characterization that differentiates themselves from one another. The only thing we know about them? Chappelle is the only one who doesn’t accept oral sex from transvestite hookers. And hey, that’s a “one to grow on” moment, for sure. But it’s too little, too late for this forgettable sketch. Luckily, it’s brief, and gets us quickly to…


“Kneehigh Park”: I’m on record as saying that Chappelle’s tendency toward gross-out humor isn’t necessarily my favorite thing about his particular brand of comedy, but that aspect reaches its zenith in this alarmingly nasty and devastatingly funny parody of Sesame Street. Staging the horrors of urban life inside a children’s show doesn’t inoculate the audience from the terrors depicted, but rather makes them approximately a dozen times worse in the process.

What helps sell the world of the fictional Kneehigh Park are the production values. They aren’t top-notch, but they are entirely believable within the conceit of the sketch. The design of the puppets is alternately adorable and hideous, and the (many) songs therein are all incredibly hummable. It’s easy to have something like Stinky The Grump’s “Fuck It” lodged in your head for hours after hearing Charlie Murphy’s deadpan delivery of the tune. And while hearing the physical manifestation of herpes warble about its persistent nature is vomit-inducing, said warbling reflects an expertly written children’s song. It’s a reminder of how many horrible things can be wrapped up in innocent packaging.


All of this brings us to the presence of the children in the sketch, which takes every element therein and magnifies them. While it’s safe to say that no child on the set heard 10 percent of what the adults actually say in the aired sketch, their very existence within this world sets the entire endeavor on edge. We saw some of this type of humor in season one, when “Make A Wish” depicted a self-absorbed Chappelle destroying a cancer-ridden child in videogame basketball. Here, the overall mood is cheerful, which makes the subversive elements stand out all the more. And yet, for all of the crassness onstage, there’s very little in the way of actual bad advice being delivered. There’s a strong anti-drug and safe sex element to every bit of the sketch. “Kneehigh High” just chooses to illustrate the worst possible outcomes of each scenario. That’s a graphic way to do it, but it’s also oddly honest. The fact that we fear for the kids in the sketch has less to do with them and more about the way in which children are overly sheltered toward such things in everyday life. That’s not to say that we need an actual “Kneehigh Park” on the air. But a middle ground between this and what normally serves as a parent-child conversation might not be the worst thing in the world.

“Episode 2-11” (season 2, episode 11; originally aired 3/31/2004)

“The only thing more spectacular than our success is our failures,” says Chappelle in his introduction to what can only be described as a “failed-clip show.” Rather than take a week off from original sketches to do a victory lap of successful sketches, this episode of Chappelle’s Show takes the time to show bits of filmed pieces that tanked during their initial presentation. The nature of the show makes it difficult to do a normal breakdown, but for sake of completion, let me list each sketch discussed by Chappelle with the audience:

“Nelson Mandela’s Boot Camp”: Chappelle stands in as the South African leader, administering tough love to juvenile delinquents on the talk show Sally.


“Def Comedy Poetry Jam”: The purveyors of Def Comedy Jam tell corny jokes.

“Frontline: Gay America”: A fictional look at two Americas: one straight, one gay.


“Haters In Time”: The characters from season one’s “The Player Hater’s Ball” use a time machine to mock Hitler and slave owners.

“Holler Dating Service”: People use a unique online service that hires men to hit on women in public on the user's behalf.


Distilling these sketches down to their bare essences gives a sense of how so many ill-advised sketches seemed like good ideas in their nascent forms. As Chappelle repeats throughout this episode, the premises themselves are usually not the problem. It’s the execution of them that caused problems.

In that sense, Chappelle’s journey through these misses serves a similar purpose to episodic reviews that have risen in popularity since the show’s demise. That in no way, shape, or form is meant to draw a direct line between what Chappelle does in this episode to what reviewers such as myself do on The A.V. Club and other websites. But it’s instructive to hear Chappelle break things down onscreen as bits of the failed sketches play out for the audience there and at home. “Here’s where we stop spinning out of control,” he notes at one point during the “Gay America” sketch, almost like he’s breaking down a failed a play from a football game. He’s not afraid to pinpoint the precise moment in which things go from bad to worse.


On the other hand, Chappelle gets to have it both ways here. He acknowledges at the outset that the show’s overall popularity has led to the opportunity to show some of its failings. So Chappelle’s Show gets to be humble, but affords itself a second chance. Many times in this episode, Chappelle will note that the initial audience didn’t appreciate the sketch, but that he himself still finds it funny. That means he can show Silky Johnson shooting a slave owner, even while saying, “Apparently shooting a slave master is only funny to me and Neal [Brennan].” He can pass off the unfunny “Gay America” sketch, while noting repeatedly that it still makes him laugh.

You can look at this episode in a variety of ways. It could be a clever cost-cutting measure that yielded an extra episode over the first season’s 12-episode order. It could be a way for the show to take a step back from its breakneck production schedule. It could be a way for Chappelle to appear grounded amid a rise in popularity. It could be a subtle “fuck you” from Chappelle to the network. I’m not sure the motivation is terribly important. This is both a throwaway episode and a Rosetta Stone to understanding the state of Chappelle’s Show at this point in time. In airing what didn’t work, Chappelle is broadcasting the sheer difficulty of coming up with strong material and the increasing disconnect between what he thought was funny and what the audience found amusing. This “greatest misses” show doesn’t reveal the Chappelle that would abandon the show early into production of its third season. But it does point to trouble on the horizon.


Stray observations:

  • Wyclef Jean appears in the “Making the Band” sketch, violently reminding me that Wyclef Jean actually exists.
  • I don’t normally talk about the musical performances on the show, but the one featuring Snoop Dogg with Tyrone Biggums and the puppets from “Kneehigh Park” is one worth watching if you can.
  • While the 11th episode was the opposite of a “greatest hits” episode, Comedy Central eventually produced five installments of The Best Of Chappelle’s Show. Four were pure sketch mash-ups, while the fifth centered on musical-related sketches and performance (some of which were initially unaired).
  • Silky Johnson’s overly complicated explanation of the premise of The Jeffersons almost justifies the existence of “Haters In Time” in and of itself. Emphasis on almost.
  • Charlie Murphy’s technique for getting into character for Buck Nasty is impossible to unsee once Chappelle points it out.
  • Next week: Wayne Brady takes over the show, and the season wraps up with Black Bush.

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