Dave Chappelle, Killin' Them Softly
Photo: Dave Chappelle: Killin' Them Softly, official trailer

Is Dave Chappelle’s Humor Too Out of Touch for a Comeback?

In light of movements like Black Lives Matter and Me Too, Dave Chappelle’s Killin’ Them Softly may be even more relevant today. But how’s his humor holding up?

Dave Chapelle has been mostly absent from the public eye since walking away from his hit series Chappelle’s Show in 2005, but now he’s back and seemingly ubiquitous. Chappelle hosted the first episode of Saturday Night Live after Donald Trump “won” the election, and in 2017 he released two pairs of new stand-up comedy specials (over four hours of material), one of which recently won a Grammy for best comedy album. His new material has been celebrated in some circles, but it has also proven to be controversial, as numerous writers and tweeters have taken issue, in particular, with his jokes about the transgender community and his commentary about the #MeToo movement. Many argue that Chappelle belongs to another era – he’s out of touch.

At a moment when Chappelle’s relevancy, and perhaps his legacy, is under debate, it’s worthwhile to consider some of his earlier material. In particular, let’s revisit a few routines from his first one-hour stand-up special,
Killin’ Them Softly, released in 2000 by HBO. When this special aired, Chappelle had already achieved a fairly high level of success as a stand-up; he’d appeared on Late Show with David Letterman and Def Comedy Jam and he had a half-hour HBO special, but he was probably most well known for playing the lead in the cult stoner comedy Half Baked (Tamra Davis, 1998). Three years later, of course, Chappelle’s Show launched him in to massive fame. Killin’ Them Softly is thus a snapshot of Chappelle on the brink of superstardom.

It reveals a comic performer at the top of his game but unencumbered by the attention and controversy that would come to define his later career, and which would increasingly become the subject of his performances. In terms of technique, the special is masterful: Chappelle establishes a rapport with his audience, and the delivery and pacing make the hour fly by. Aside from some political material about the Bush v. Gore election, the Clinton/Lewinsky scandal, and some very dated “if there were a black president” jokes, there’s little to mark the special as being nearly 20 years old;
Killin’ Them Softly remains as relevant now as when it was released. And while Chappelle clearly uses the devices that many viewers both now and at the time associated with African-American comedy, he adapts those devices in such a way that the material rarely feels stale or predictable.

The first thing we should notice about Chappelle’s performance in
Killin’ Them Softly is the way in which he presents a comic personality. It’s a common misperception that successful comedians are successful because of their jokes. But we often laugh as much at the person—the comic persona presented onstage—as we do at the actual material. For example, think of Chris Rock’s preacherly call and response style as he struts across the stage or of Sarah Silverman’s feigned cluelessness. For an extreme example, think of an explicitly fictional stage persona like Larry the Cable Guy. Chappelle’s onstage persona feels less overtly performative than those comics, as he successfully creates the illusion that he is not at work but is just “hanging out”. To this end, one of his first comments in the special is, “I know! It’s been a long time,” as if he’s catching up with an old friend. Along similar lines, Chappelle has a method: after telling a particularly funny or surprising joke, he doubles over in feigned laughter as if he can’t believe what he just said. Sometimes, he even jogs around the stage a bit while the audience laughs with him. The move works rhetorically like a sitcom laugh-track—letting the audience know we should find this bit particularly funny—but it also obscures the fact that we are watching a performance that has been written and practiced over time. It seems Chappelle is just as surprised (and amused) with what he is saying as the rest of us.

Chappelle’s relaxed style and persona is likely a key reason for why he was able to joke so successfully about sensitive issues in the past. (In his recent and more controversial specials, Chappelle often abandons the laid-back slacker charm of his younger years to adopt a professorial attitude). Take, for example, the ways in which race is discussed in
Killin’ Them Softly. Throughout the special, Chappelle confronts police brutality, white privilege, and systemic inequality in ways that are somehow both honest and lighthearted. He has things to say but avoids being preachy. In one of the funniest bits, Chappelle explores the ways in which police treat white and black people differently. To do so, he tells two stories about encounters with the police that he had while hanging out with his white friend, Chip.

The character Chip, like Chappelle’s onstage persona, is constructed as a stoner/slacker type. The crucial difference is that due to his whiteness, Chip remains blissfully unaware that encounters with the police, even when drunk or high, could be dangerous. In the first story, Chip stops to ask police officers for directions, reaches out and touches the policeman, and admits to being high. In the other, Chip is pulled over after speeding and zig-zagging across lanes while drunk. In this instance, Chip says simply, “I’m sorry officer. I didn’t know I couldn’t do that.” At the end of both stories, the white police officer simply tells Chip to “get out of here!” Chappelle, in each instance, is amazed that Chip was not arrested, beaten, or abused by the police.

The bit is successful for a variety of reasons. Chappelle—a skillful mimic, as we know from
Chappelle’s Show—acts out the narrative, playing the roles of three distinct characters: Chip, the white police officer, and himself. Throughout the routine, he adds his humorous commentary: “A black person would never dream of talking to the police high. It’s a waste of weed!” The most original aspect of the bit, though, is the nuanced vision of race relations that it presents. Like Eddie Murphy’s “White Like Me” sketch, in which Murphy goes undercover as a white man to expose the privileges of white America, Chappelle uses exaggerated humor to suggest that white and black people live in very different worlds. But Unlike the Murphy sketch, Chappelle uses an interracial friendship (rather than a disguise) to expose the truth of white privilege. The result is that Chappelle manages to critique racism while avoiding a simplistic white vs. black vision of race relations. After all, Chappelle and his white friend Chip are in the car together and seem to hang out a lot. Chip emerges not as racist but as the clueless beneficiary of a racist system.

Let’s also consider Chappelle’s comic impersonation of his friend Chip. Probably the most famous comic device used by black comedians in the US is the impersonation of white people. Richard Pryor, Eddie Murphy, the Wayans brothers and a score of lesser-known comedians have all impersonated white people. In her book
Laughing Mad: The Black Comic Persona in Post-Soul America (Rutgers University Press, 2007), African-American humor scholar Bambi Haggins refers to this as “white people be like” jokes (187). In these sorts of jokes, the white person is usually presented as nervous, uptight, and decidedly dorky. In the above-mentioned Murphy sketch “White Like Me”, Murphy practices for his white undercover work by reading Hallmark greeting cards, watching Dynasty, and keeping his “butt tight”. The effect here is to reinforce the idea that black people are looser, cooler, and hipper than white people.

Chappelle complicates the formula, though. His impersonation of the white police officer is in keeping with the uptight white person routine, but Chip is another story. To most listeners’ ears, Chappelle’s voice for Chip will certainly read as white, and Chappelle does suggest some dorkiness to the character (for example, the song that Chip plays while drunk-driving is Twisted Sister’s “We’re Not Gonna Take It”). However, it should be noted that Chip is ultimately portrayed as the more relaxed of the two, and it’s Chappelle’s version of himself in the story that comes across as nervous. This depiction makes perfect sense for a routine exposing white privilege, but it also inverts one of the most common devices of African-American humor. At other moments in the special, Chappelle continues to complicate his performance of whiteness by impersonating, among others, a Southern racist, a 1940s movie gangster, a 911 operator, and Bill Clinton.

It’s no surprise, though, that Chappelle’s humor about race is complicated and intelligent. This is the sort of humor for which he later became famous on
Chappelle’s Show. His jokes about gender, however, are another story and have earned him his most direct criticism. Even before the overtly controversial material of his recent stand-up sets, many viewers noticed how gender-driven Chappelle’s Show sketches like “New York Boobs” are less than insightful.

For the most part, this is also true with Killin’ Them Softly. Unfortunately—after 45-minutes of sustained brilliant comedy—Chappelle decides to end his special with about 15 minutes of material about relationships between men and women. Much of the material here is funny, but it is also very conventional and seems a bit rote. There’s a bit, for example, about how men only desire women whereas women desire things. In this formula, men get things only to attract women. In another bit, he critiques the bad advice that magazines give women with articles like “100 Ways to Please Your Man”. Chappelle asserts there are only four ways: “suck his dick, play with his balls, make him a sandwich, and don’t talk so much.: Chappelle achieves laughs from such bits, but really, any competent comedian could, and most have.

Killin’ Them Softly’s most insightful moment related to gender politics comes not during this final sequence but earlier, when Chappelle discusses the harmful effects of the media on young people.

Chappelle bgins the sequence by asserting that the “they use the media to program us at a young age.” He goes on to discuss watching with his nephew an old Looney Tunes cartoon featuring the amorously aggressive skunk Pepé le Pew. Chappelle is at first excited to watch the cartoon with his nephew, but is soon horrified by the skunk’s behavior: “Good God! What kind of fuckin’ rapist is this guy?” Chappelle is even more dismayed when, a moment later, his nephew says the cartoon taught him that “sometimes you gotta take the pussy.” Chappelle doesn’t explicitly frame it this way, but the bit is a clear denouncement of rape culture. While Chappelle’s gender politics are usually inconsistent and sophomoric, the joke here displays a real understanding of the ways in which the media and other systems of power intersect to create a culture’s value system.

This is made clear as Chappelle continues his critique of children’s television. He next turns his attention to
Sesame Street‘s depiction of Oscar the Grouch and asserts that the character teaches children to hate homeless people. When called a grouch, Oscar—via Chappelle’s impersonation—protests that he lives “in a fucking trash can! I’m the poorest motherfucker on Sesame Street.” happelle next imagines a Sesame Street viewer growing up to become the sort of adult who would dismissively walk by a homeless person on the street and say, “get it together, grouch.” Once again, Chappelle shows a keen awareness of the ways in which media shapes values, and he demonstrates how it does through relatable examples. Most important, though, he never forgets to be funny even when discussing serious topics.

More than any other routine in
Killin’ Them Softly, this discussion of media representation most clearly anticipates Chappelle’s career trajectory. Five years after suggesting that Pepé le Pew teaches boys to be rapists and that Oscar the Grouch teaches children to hate homeless people, Chappelle walked away from a lucrative TV show after wondering what his own racially-driven humor may have been teaching viewers. In his Netflix special 17 years later, The Age of Spin, Chappelle makes the controversial argument that Bill Cosby’s legacy should “not be thrown away” even though he “probably does rape”. Chappelle defines this legacy primarily in terms of media representation: for example, Cosby’s cartoon was the first ever to have black characters that were not drawn as racist caricatures, and Cosby hired a clinical psychologist to ensure that The Cosby Show had no negative representations of African-Americans. On the one hand, these comments again underscore Chappelle’s habit of seeing more nuance in racial issues than in those related to gender. On the other, they show how the topic of media representation is central to his worldview. The issue becomes a through line in Chappelle’s career and may serve as a marker of his own legacy.

Stand-up comedy is an art form that makes us laugh and that can simultaneously offer profound insights into the world we live in. However, stand-up—like political cartoons or late night TV—also runs the risk of fading into irrelevancy, or,worse, of becoming a painful reminder of how wrong we used to be. As a child, I remember laughing for hours at Eddie Murphy’s
Delirious (1983) and Raw (1987). Today, the homophobia is so blatant and aggressive that I can’t make it 15minutes in. Killin’ Them Softly, though, holds up, and in light of movements like Black Lives Matter and Me Too, may be even more relevant today. Perhaps, 20 years from now, we’ll be saying the same thing about Chappelle’s new group of controversial specials. If not, we’ll still have this one.