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Chappelle’s Show: “Episode 1-1”/“Episode 1-2”

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“Episode 1-1” (season 1, episode 1; originally aired 1/22/2003)

In which the show finds itself nearly cancelled before it even starts…

It’s hard to imagine a television landscape without the influence of Chappelle’s Show. But that being said, it’s a lot easier to do so now than just a few years ago. There’s a half-life to the lasting power of certain pop culture artifacts, one that seems to be rapidly diminishing with the exponential increase in output. Movies are on DVD seemingly before they leave theatres. Last month’s pop music phenom is today’s bargain bin. And naming every show cancelled on television this year alone is a fool’s errand. There’s no lack of scarcity when it comes to objects we can consume, but there’s a limit to what we can actually absorb. So while the final, controversial season aired only six years ago, it feels much longer. What I want to explore this summer in rewatching the entire series is twofold. I want to first examine each episode anew, having not watched anything outside of the most popular sketches in the years since it went off the air. Secondly, and more importantly, I want to look at what remnants of this show still exist in the television landscape today. Does this show indeed still carry weight in the modern television landscape, or is this a hermetically sealed piece of history?


Chappelle’s Show starts off with an unassuming, almost-instantly dated sketch. While the show debuted less than ten years ago, it’s still slightly disconcerting to see a parody of a commercial most of us will have long forgotten be the introduction to the program. When I pitched this program as part of the TV Club Classic series, I wanted to see how well this show held up after its meteoric rise and equally rapid descent in the middle part of this century’s first decade. And what is the first thing that greets me on this journey? A Mitsubishi mockery. It’s certainly funny without the context, but doesn’t have the staying power of the show’s more powerful moments. We’ll see a lot more of these as the season goes on, but these types of sketches are both inevitable and well within the structures of other sketch shows such as Saturday Night Live and In Living Color. Timelessness isn’t always the goal for these individual segments. Sometimes, timeliness is paramount.

From there, the pilot moves onto the Popcopy sketch, one of the two that Dave Chappelle and co-creator Neal Brennan presented as part of their initial pitch. Featuring Michael Rappaport and Guillermo Díaz, it’s a training video designed to explain why people in copy shops are so damn unhelpful. Chappelle is strong as an overly chipper manager, with his mischievous eyes always betraying the true intent of the seemingly innocuous advice he dispenses. It’s a shaggy, underproduced segment, but while that allows the seams to show in Rappaport’s contributions, it allows Díaz’ manic energy to shine through. My favorite detail? Chappelle’s suggestion to tell customers the store’s computers runs on Linux should they bring both Mac- and PC-compatible files. It’s a small, nerdy detail, but shows the intelligence brimming underneath the fecal jokes that stain (literally) the end of this segment.

Following this is a short segment in which Nat King Cole treats a woman in a fictional 1956 Christmas special as poorly as Dr. Dre does in his “Nuttin’ But a G Thang” video. It’s designed to demonstrate that misogyny didn’t spontaneously form with the advent of hip hop. But in the DVD commentary track, Brennan reveals it’s as much a parody of MTV ever thinking it was OK to show Dre dumping malt liquor on a dancer in the first place. It’s a subtle but important shift, one that Chappelle’s Show constantly achieved: It placed as much blame on the institutions that allow things to happen as much as those that perpetrate them. It’s something to keep in mind as the show’s content took on a life of its own and Chappelle started to question his own moral compass.

A brief but forgettable “Human Stenographer” sketch (in which people hire a person to transcribe their everyday conversations) gives way to the single most important thing about the pilot, and maybe the most important thing in the show’s history. “Frontline: Clayton Bigsby” is the polar opposite of the Eclipse sketch that opens the program, and it’s tempting to look at that introductory sketch as the lure in order to snare rapt viewers to actually watch the important part of the episode. Saying that Bigsby’s black white supremacist is an important character might sound hyperbolic, but this is brave, shocking sketch that stands the test of time. In fact, given the racial politics at play in the country right now, this might be even more relevant now than in 2003.


The sketch starts out with Chappelle onstage predicting that the sketch will probably ensure that a second episode would never happen. Indeed, it’s sort of crazy that Chappelle’s Show featured this in its premiere installment. It’s a gutsy move, but one that also indicated the type of show this could be going forth. This wasn’t simply a show designed to make you laugh, but also make you think. In the commentary, Brennan and Chappelle flesh out the anecdote Chappelle makes onstage about showing it to a friend of his who insinuated that Chappelle had set African Americans back simply by producing it. That friend? Cey Adams, a graphic artist for Def Jam that designed some of the label’s most famous album covers. He’s also a feminist vegetarian who never curses. Adams compared the sketch to the moment Adam Horowitz used the “n” word onstage at the Apollo Theatre. And Chappelle’s Show fought to air it in the pilot anyways.

And yes, we’re at the “‘n’ word” portion of the review, so it’s probably worth it to present in full the typographical introduction to the “Frontline” sketch in its entirely. It’s both a warning and a Rosetta stone to understanding the complications that Chappelle’s use of racially-charged language would unleash in the dialogue in and around the show.


“Warning: For viewers sensitive to issues of race, be advised that the following piece contains gratuitous use of the ‘N’ word. And by the ‘N’ Word, I mean ‘nigger.’ There, I said it.”

Like Richard Pryor, George Carlin, and dozens of other comedians before him, Chappelle is incredibly interested in the contextual power of words. How and why does meaning change based on the person saying it? Can a word be reclaimed as an act of empowerment? When Bigsby uses the “n” word, it’s ironic. But when he hurls it at a group of white teenagers, they take it as the ultimate compliment. That Chappelle is more interested in the meaning behind the word rather than the word itself is often self-evident. But it doesn’t make discussing it particularly easier. Yes, in that written intro, Chappelle says it. And yes, throughout this sketch and dozens more over the course of the series, he and others say it again. But rather than defanging or reclaiming the word, Chappelle’s Show went on to complicate it.


How it complicated that word (and others we’ll explore in the future) will be left to later discussion. For now, we can marvel at the way William Bogert (Small Wonder) plays the befuddled straight man to Chappelle’s blind racist, a man raised to believe he was Caucasian. It’s a nature/nurture argument in which nurture wins handily. Even when confronted with seemingly incontrovertible evidence that he is African American, Bigbsy refuses to acknowledge the truth. The great statement of the segment? Those following Bigsby’s racist rants are as blind as he is, metaphorically speaking. It’s something the lengthy piece never explicitly states. But in the nearly nine minutes that this “Frontline” sketch runs, we see a host of people so settled in their ways that they willingly turn a blind eye to anything that doesn’t fit their long-held beliefs. If Chappelle’s Show tried to do anything over the course of its run, it was to shine a light on elements of society most people would rather not acknowledge. It rarely let its characters grow, but always left room for the audience to learn.

Unfortunately, the audience didn’t always seem to learn the right lesson. But we’ll get to that soon enough.


“Episode 1-2” (season 1, episode 2; originally aired 1/29/2003)

In which the world meets Tyrone Biggums…

It took quite a while for The Chappelle Show to truly find its own voice. But there’s a confidence in trying out potentially explosive topics that resides in even the earlier episodes. Sure, “Frontline” and Tyrone Biggums are the sketches most people would remember from these first two installments. But there are plenty of other material in the 15 minutes of actual sketch time in the second episode that indicate a willingness to poke cultural hornet’s nests whenever possible. (The 15 minutes doesn’t account for the Mos Def performance at the end, the first of many musical acts to close out episodes.) Chappelle’s Show rarely did this for shock value. Rather, it explored the pervasive issues of race, gender, and sexuality in all aspects of culture, and repeatedly pointed out the elephant in the room.


The opening segment is a great example of this. Chappelle is already establishing himself as an anti-establishment figure, one seemingly getting away with things despite corporate disapproval. But his secret weapon throughout his run isn’t the anger with which he delivers his insights, but rather the warm, intelligent, slightly mischievous way in which he deploys each punch line. Bringing up a female Caucasian opera singer provides plenty of comedy through the dissonance of what he scribbles for her to sing versus how she actually intones it. But Chappelle’s “Can you believe I’m getting paid for this?” grin sells the delivery just as much. This isn’t someone raging against the machine so much as someone delighted that he has the platform from which to speak. That grin doesn’t dull the blade of Chappelle’s comedy. That grin both respects the intelligence of the audience smart enough to understand what he’s doing. But it’s also a mechanism to trick those that might not otherwise watch a four-minute segment about racial identity in public speaking.

After a quick, dated “Real Sex” bit, the episode unveils “Dave Chappelle’s Educated Guess Line.” What feels like another dated segment (one based on those once ubiquitous Miss Cleo ads) turns into one of Chappelle’s favorite topics: the shorthanded use of racial stereotypes in everyday discourse. Chappelle’s “psychic” based his observations purely on racist assumptions. He listens to a woman complain about how her new boyfriend doesn’t appreciate her sizeable rear end in comparison to her old boyfriend, and accurately depicts the race of everyone involved. When he gets a collect call from prison, he knows before a word is uttered that 1) the inmate is African-American, and 2) that the same man will be in prison six weeks after his upcoming release after committing the same crime that landed him in jail in the first place.


The lesson here is that some stereotypes are true, no matter how much we would like them not to be so. Chappelle doesn’t place blame or anger at any particular race. But he also doesn’t pretend stereotypes exist without any basis in fact. The ways in which people live up to these preconceptions is a pervasive theme throughout the show’s run, but he’s rare to judge anything other than “stupidity” when it comes to actually looking down on anyone in particular. Chappelle’s Show earned a lot of praise for this approach, although its lack of outright didacticism also caused a significant amount of problems for him later on. While touring at the height of the show’s popularity, Chappelle lashed out at a Sacramento audience who wouldn’t stop screaming, “I’m Rick James, bitch!” during a live show. “You know why my show is good?" he asked them mid-performance. "Because the network officials say you're not smart enough to get what I'm doing, and every day I fight for you. I tell them how smart you are. Turns out, I was wrong. You people are stupid.”

A brief and unmemorable “Wrap It Up” sketch is followed by something anything but stupid: the first appearance of crackhead Tyrone Biggums, who speaks to a group of children about the ills of drugs. Naturally, he ends up glorifying them to the point where the children are taking notes about the best way to steal cash so they can trip balls on acid in order to sing songs with Bugs Bunny while eating cookies. If Chappelle’s Show pushed the envelope on what it discussed, it also pushed the envelope with whom it involved in the discussion. While much of this Biggums sketch seems stitched together (with several bits clearly filmed without the children in the room), it’s still pretty shocking to see Biggums delivering some of these lines to a roomful of pre-teens.


But again, it’s not about Chappelle pushing the envelope in order to shock people for shock’s sake. He’s pushing the boundaries about what’s acceptable to actually discuss in the open. He didn’t invent the concept of a crackhead. He decided to demonstrate what happens when parents don’t take an active role in the education of their children. That twist alone justifies the existence of the sketch, with the teacher’s horror implicitly noting that parental and education ignorance allowed Tyrone in the school in the first place. Is this overthinking what’s essentially a silly premise? Probably. But the segment supports this analysis, which is a good thing. Chappelle’s Show always wanted to make you laugh. But more importantly, it made you want to think. If Biggums offended you, the show forced you to confront why it did so. And by forcing the audience to confront things it would have rather continued to ignore, Chappelle’s Show did more good than just about any show on the air this century.

Stray observations:

  • Chappelle flubs his first monologue, saying “bleeper” instead of “blooper”. But he quickly recovers, and turns it into something funnier than originally planned. That Chappelle’s Show allowed the flub to stay speaks to the way the show embraced improvisatory moments throughout its run as features, not bugs.
  • According the DVD commentary, that’s co-creator Neil Brennan’s head that explodes during the “Frontline” segment.
  • Not everything about Chappelle’s outlook on life is particularly flattering, but he doesn’t hide from his leeriness of gay males or short people of any particular persuasion. Having such thoughts aired isn’t something to necessarily be lauded, but he’s also not hiding the less savory aspects of his personality either.
  • “America’s at war with Al Qaeda. But we’re still losing the war against Al Sharpton!” This is a line I’m sure people at Fox News utter all the time to this day.
  • Chappelle has the opera singer declare that Comedy Central won’t share ad revenue with him. Two years later, he walked away from a $50 million dollar deal with them. How quickly things change.
  • The plan for this summer: I’ll cover two episodes per week as a general rule. Given that season two has thirteen episodes, I’ll cover three episodes of that year at once. I’ll also cover the third, Chappelle-less season as a whole in the finale week of the series. There’s not a lot to cover there, except for one fascinating segment involving the in-studio audience.