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There’s an increasing sense within Chappelle’s Show, as it works through its second season, of its growing popularity. This week doesn’t get meta per se, but one can see increasing examples of the show understanding that it’s part of a growing cultural conversation. In some cases, that knowledge emboldens it to try new things. In other cases, one can already see the tensions as Chappelle’s Show moves on from the idiosyncratic viewpoint of a single comedian into a program expecting to be all things to all people. We have time to discuss that shift in the final few weeks of our coverage here, but it’s worth keeping in mind all the same as we delve into this week’s solid double dose of the show.


“Episode 2-8” (season 2, episode 8; originally aired 3/10/2004)

“When Keeping It Real Goes Wrong”: This being Chappelle’s Show and all, it makes sense that Dave himself appears in nearly every sketch. Outside of Paul Mooney’s output for the show and the occasional short, pre-packaged segment (such as “Third World Girls Gone Wild”), we expect the star’s presence in every sketch. So it’s a bit surprising to see him absent from this, the third installment of “Keeping It Real” in three weeks.

Still, he’s not missed, as the protagonist Brenda (who also ends up serving as her own antagonist) is a strong comedic presence, taking her fears about her man’s infidelity to epic heights. A wrong number turns into a one-woman mission to exact revenge on the woman she suspects is stepping out with her boyfriend Jamaal. Brenda looks up the address online via reverse directory, and proceeds to deface the car in the driveway. Unfortunately, the car doesn’t belong to Janice, who accidentally misdialed Brenda, but to Janice’s brother. Because he’s a federal agent, and defacing federal property is itself a federal crime, Brenda gets six years in prison and a constant beatdown from a crew that, in the words of the narrator, “kept it realer.” This is, I believe, the last iteration of this sketch, and that’s a good thing. This series of sketches isn’t a Chappelle’s Show lowlight by any means, but it’s more fascinating to see in how many ways Chappelle’s comic mind could stretch, and we get some very interesting directions in these final few episodes of season two. Speaking of which…


“I Know Black People”: This segment is actually in two parts, both of which bookend the episode. But because it’s all part of a single entity, arbitrarily broken up by “rounds” that don’t actually matter, I’m treating this as one sketch for the purposes of our discussion. In his opening monologue, Chappelle notes that the inspiration for the game show came from a white viewer of the show who called the program offensive… to black viewers. Rather than be completely offended, Chappelle pivots and wonders if, perhaps, this white viewer is someone that is simply in tune with the concerns of black people. Thus, he creates this game show as a Myers-Briggs-esque test to survey a cross-section of New York citizens and find a “winner.”

I put “winner” in quotes because this is less about competition and more about sociological survey. Whereas man-on-the-street segments such as “Ask A Black Dude” feature people asking celebrities questions, here the tables are turned. As Chappelle notes in his introduction, nothing but the questions themselves are scripted. Instead, Chappelle lets a variety of people (including, but not limited to, a professor of African-American studies, a police officer, a writer on his show, a Brooklyn barber, and a Korean grocery-store employee) answer questions such as “What is a chickenhead?” and has them fill in cryptic television theme song lyrics. It’s a lengthy segment, nearly rivaling the Rick James “true Hollywood stories” installment. And while Rick James is rightfully legendary, “I Know Black People” is my favorite sketch that Chappelle’s Show ever did.

A few things take “I Know Black People” to such amazing heights. The first are the questions themselves, which marry “easier” inquiries with more difficult ones. But the point is never to make someone look bad through their answers. This isn’t “gotcha” comedy, designed to make Chappelle look superior to those he’s putting through the game show. Many do not know the answers, but their guesses often provoke amazement, not derision, from Chappelle. When Chappelle’s Show writer Bryan Tucker mistakes a “loosey” (a single cigarette) as another word for “oral sex,” Chappelle notes that such a definition probably should be incorporated into the popular lexicon. Getting correct answers is almost beside the point. Opening up a dialogue is the endeavor here.


In that regard, some of the replies speak to some deep-seated cultural beliefs. The Korean grocery-store employe had never seen Good Times, but correctly guessed that the character Bookman was a janitor. That assumption fascinates Chappelle, who can’t believe the contestant could guess so accurately. And yet, Chappelle can believe it, not because he thinks the grocery-store employee is racist, but because it’s not a horrible guess to assume a character discussed on a game show called “I Know Black People” might have played a janitor on a 1970s sitcom. None of this cultural baggage is openly discussed, but everyone watching intuitively understands it. It’s not right that this contestant guesses correctly. But the fault doesn’t lie with him.

If there’s a stand-out contestant, it has to be the barber, who delivers memorable answer after memorable answer. They are blunt, rude, semi-shocking, but never delivered maliciously. Even if he gives the “wrong” answer, the offscreen judges often award him points for sheer bravado. One question, “Is pimping easy?,” is designed to elicit an answer of “no.” And indeed, most participants answer this way. But the barber, when asked, cocks his head to the side and nonchalantly replies, “Hell yes!” Chappelle hears the bell, looks at the camera, and says, “Somehow that is correct!”

Chappelle’s responses are the not-so-secret secret weapon here. As mentioned before, his function as host is inclusive rather than exclusive. He’s not looking for politically correct responses, and he generally celebrates honesty. When the slightly embarrassed police officer notes that children in her patrol area say she has a badonkadonk, Chappelle amusingly notes, “I’m tellin’ ya, Washington Heights… they’ll tell a cop they have a badonkadonk!” When people are struggling to correctly sign “the most controversial of all the Good Times lyrics,” he sings along with them in order to help them answer correctly. Antagonistic humor has its place in the comedic spectrum, but it’s rarely found in Chappelle’s Show. When it does occur, it’s usually aimed at political and financial institutions. It’s rarely aimed at individuals trying to live their lives as best they can. And the melting pot on display in “I Know Black People” is both Chappelle’s Show at its warmest as well as its funniest. As we’ll get to when discussing the show’s third season, the types of observations that inspired this sketch didn’t always lead to conversations like this. But that makes the times that they did all the more meaningful.


“Episode 2-9” (season 2, episode 9; originally aired 3/24/2004)

“Sales Pitches”: Wow, this is apparently a sketch that exists. If you told me this once aired on basic cable, I would call you a liar. Turns out, I’m just old and suffering from memory loss. In the episode’s introduction, Chappelle notes that two things have started to happen while filming the second season. The first? People have started yelling out catchphrases at him more often. Secondly? People have started to pitch him ideas without warning. Both phenomena bother Chappelle, but only the latter gets the sketch treatment here.

While at dinner with his wife, a man named Frank comes up to pitch Dave on a movie in which Chappelle would star as underground street poet “Colt .45.” We don’t really hear much of the pitch, but instead live inside Chappelle’s thoughts to distract himself from the interruption. The thoughts include quick hits (“bicycle, monkey, Ashy Larry”) but also longer sequences in which Arsenio Hall raises hell over being uninformed about the quality of the cheese at a posh party or Chappelle has a career as a rapper who wears sheep legs onstage. (“I’m the real black sheep!” he declares onstage.)


Chappelle only perks up when he hears the $12 million offer to star as Colt .45, at which point he starts pitching ideas back. Naturally, Frank daydreams himself (about NASCAR and diapers), while Dave’s wife imagines Anthony Anderson playing what seems like the Mena Suvari part from American Beauty. The weirder parts of this sketch make this tolerable, but after the genius of “I Know Black People,” anything would be a letdown.

“Dave Gets Oprah Pregnant”: There’s little point in trying to psychoanalyze this sketch. One could, in theory, try to break down why Chappelle might fantasize about knocking up Oprah Winfrey in order to quit his job and mooch off of her for the rest of his life. One could then hypothesize as to why Oprah puts up with it all. I mean, it’s totally possible to do so. But I’m not sure that’s the proper approach. Rather, looking at this from the perspective of Chappelle being the biggest a-hole possible, it’s pretty damn funny. Sure, he made everyone look good in “I Know Black People.” But just like in season one’s “Make A Wish” sketch, he’s never afraid to make himself look terrible.

Chappelle burns every bridge possible along the way to what he perceives as his meal ticket. The first thing he does upon learning about her pregnancy? Screaming “Gotcha, bitch!” then telling everyone at Chappelle’s Show just what he thinks of them before quitting. Once safely ensconsed in Oprah’s mansion, he lounges about, gets happy endings with his massages, practices karate with Bruce Lee’s brother, paints nude models, and karaokes late into the night. Ultimately, the joke’s on him—the baby looks like Dr. Phil. Chappelle vows revenge, and we get a “To Be Continued” after he punches a Stedman Graham lookalike. We never get the supposed second half of this sketch, which just means Chappelle’s Show occasionally had the same problem ending sketches that Saturday Night Live does. But even if this sketch ends halfway through its metaphorical sentence, it’s still a fun exercise in a man behaving badly.


“Jury Duty”: Chappelle notes that co-creator Neal Brennan always thinks Chappelle doesn’t believe any black celebrity is guilty during a high-profile trial. “And the reason he thinks that,” says Chappelle, “is that I never think they’re guilty.” What follows is a series of potential juror interviews in which Chappelle attempts to dismantle cases against O.J. Simpson, Michael Jackson, and R. Kelly. (He’s also questioned about the Robert Blake trial, but seems to be fairly certain about Blake’s guilt.)

If you wanted to break down Chappelle’s arguments via pie chart, you could assign about one-third to legal obfuscation, one-third pure nonsense, and one-third moral outrage. The first third takes the form of him attempting to push past what seems obvious to the district attorney, either by looking at the evidence from a new slant or offering up potential reasons why the victims and/or their families might be acting in the manner they are. The second third takes the form of intentional misdirection, leading the prosecution down bizarre paths in order to derail their line of questioning. When the DA prosecuting Jackson notes that similar charges have been leveled against him before, Chappelle replies, “Some people say cucumbers taste better pickled.” It makes no sense at all, and the “What?” and “Huh?” replies the two then exchange are as funny as anything the show does this season.

But it’s the latter third that’s the richest, because Chappelle’s stances stem less from the belief these men are innocent and more from the fact that the black community has unjustly suffered within the legal system for so long. He can’t admit that O.J. Simpson might possibly be guilty, saying, “Sir, my blackness will not permit me to make a statement like that.” His increasingly elaborate criteria for “reasonable doubt” in the R. Kelly trial has less to do with Chappelle’s love of his music and more about his outrage over the Rodney King verdict. Now, Chappelle doesn’t lay any of this on too thickly, and so it’s perhaps easy to miss that this level exists at all. But there’s an anger under the absurdity that makes this one of the strongest sketches all season.


Stray observations:

  • “I Know Black People” ends with Chappelle asking the contestants, “How can black people rise up and overcome?” People offer up a variety of answers, all of which are deemed correct, except one: “Get out and vote.”
  • The girl from season one’s “It’s A Wonderful Chest” appears as one of Chappelle’s coworkers in “Dave Gets Oprah Pregnant.”
  • The laundry list of things that would have to be in a videotape of R. Kelly committing a felony to convince Chappelle is just amazing. I’d list them out, but I’m sure an entire thread below will be dedicated to itemizing them one by one. Don’t let me down, fair readers.
  • Next week: Chappelle takes on P. Diddy, and airs some of the show’s greatest misses.