The ‘80s had Eddie Murphy; the ‘90s had Chris Rock; the millennium had Dave Chappelle. The DMV great, who’s been performing stand-up since he was 14, combined some of Murphy’s comedic acting ability and Rock’s raw political insight with his own incisive social commentary to become undoubtedly one of this century’s most revered comedians. Introduced to many as a witty, scrawny dude pantomiming biting a penis off on HBO’s Def Comedy Jam, Chappelle spent the ’90s killing it as a late-night show guest; appearing in The Nutty Professor, Con Air, Forrest Gump, and cult classic Half-Baked; and brought in the new decade with his excellent HBO special, Dave Chappelle: Killin' Them Softly.
It’s enticing to be the contrarian that argues Chappelle has so much more to offer outside 2003 and 2004. You’d be right, but anyone who doesn’t put Chappelle’s Show at the center of his legacy is kidding themself. Dave’s masterpiece created pop culture moments at an insane rate—the R. Kelly spoof, the Player Hater’s Ball, Clayton Bigsby, and Tyrone Biggums all appeared in the first season alone, and that wasn’t even the show’s best.
But Chappelle’s Show made its star too famous. Chappelle had to contend with a mainstream audience possibly laughing at his jokes—many of which dealt with the surreal nature of being a black man in America—for the wrong reasons. Chappelle has specifically pointed to a skit in which he’s a blackface pixie who convinces black people to act stereotypically. One white man’s laugh during the bit threw him off. "When he laughed, it made me uncomfortable," Chappelle told Time. "As a matter of fact, that was the last thing I shot before I told myself I gotta take f****** time out after this. Because my head almost exploded."
So Chappelle’s Show had to go, and Dave spent the better part of last decade out of the spotlight. But he bounced back when he was ready, booking multi-night residencies at Radio City, dropping four Netflix specials in a $60 million deal with the streaming service, and hosting his first Saturday Night Live. From now back to his prime, and in honor of his 45th birthday, here are the best Dave Chappelle bits.
Election Night
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Show: Saturday Night Live (2016)
Dave Chappelle had the unenviable task of trying to make America laugh as an Emmy-winning Saturday Night Live host days after its citizens found out Donald Trump would be the next president. He’d regret saying we should give Trump a chance in his opening monologue, but even with that slip-up, the show was mostly a success that featured the return of some Chappelle’s Show characters and A Tribe Called Quest. The episode’s most salient bit would come early in the episode: Chappelle and his friend, special guest star Chris Rock, watch the “Election Night” results pour in alongside their disheartened white pals. “God, this is the most shameful thing America has ever done,” Beck Bennett’s white liberal says. Rock and Chappelle, and the rest of Black America tuning in, share a laugh.
Black National Anthem
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Show: Def Comedy Jam 25 (2017)
The 25th anniversary celebration of the HBO series of course had its alumni performing brief stand-up bits and jokes. Still, Def Comedy Jam 25’s most hilarious moment was an improvised one. Chappelle makes a poignant point about being black in America before an upbeat 808s beat throws him off. After riffing a bit, Chappelle admits he’s been wearing glasses because his “eyes cross” when he reads: “I’ve been nervous all night. I’m not scared of the crowd. It’s just like, ‘What I gotta do? READ?!’”
It’s not the best lead-in to a hymn for African-American advancement. Still, the impromptu sing-a-long of the Black National Anthem somehow fits.
Whose Baby Is This?
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Show: Killin’ Them Softly (2000)
Chappelle’s absurd plot twists are a signature feature of his routines. In this bit from his pre-Chappelle’s Show gig, Chappelle is an innocent limo passenger whose night takes a left when his driver decides to make a detour. Our protagonist slowly realizes where exactly they’re heading: “I’ve never been there before. I’m not sure if it was a project. But it certainly had all the familiar symptoms of the projects.”
Comedians suddenly swerving left during a story isn’t a new concept, but Chappelle stands out in the way he delivers his detail. You knew you were in for something great when he threw in that tick-tick-tick of a crackhead scampering about, but the joke truly lives for that weed-dealing baby. It’s a wild image, but then again, the hood is a wild place.
R. Kelly
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Show: Chappelle’s Show (2003)
Part of what made—and makes—R. Kelly’s continued relevance infuriating was that this was an alleged serial sexual predator building his career off singing about sex. The infamous pee tape that landed R. Kelly in court gave Chappelle more than enough material to put a lowbrow spin on it. In an early Chappelle’s Show highlight, the star’s sense of comedic timing and R. Kelly’s eccentric phrasing meet for instant quotables like, “Close your eyes, show me your face...I’m gonna piss on it.” The skit (and the “remix edition of the song about pissing”) quickly turned R. Kelly into joke fodder. Unfortunately, Kelly would go over a decade without suffering any lasting consequences.
White Boy Chip
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Show: Killing ‘Em Softly (2000)
It’s a classic setup: A black man watches his white friend gets away with various Caucasian acts—that is, getting away with mischief solely because you’re white. Chappelle’s use of this idea works because his expressiveness evokes the shock and confusion any self-aware black man would have in that sort of situation. In this bit, Chappelle’s white friend Chip manages to touch a cop multiple times while high and get away with just mildly annoying the officer. He pushes his privilege even further in a separate incident by saying he must race a police officer during one traffic stop. Chappelle, too high to know any better, simply says, “Well, n****, sometimes you gotta race. I don’t know.”—big risk if you’re black.
Mad Real World
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Show: Chappelle’s Show (2003)
This longer-than-average sketch introduces us to Mad Real World participant Chad, who happens to be the only non-black member of the parody’s cast. Over the course of his stay, he get incapacitated by a sleeper hold, his girlfriend has sex with three of the house’s guests (including a guest’s friend who just got out of jail), and his father gets stabbed when a female cast member gets pissed after he allegedly looks at her the wrong way. “I don’t know what I did,” he says as he bleeds. Dave Chappelle’s Tron—who likes pouring cognac in his blended juice—responds by pretty much laying out the point of the premise to the audience: “Got in a house with six wild n****s is what you did.” Then you wonder: is this what cast directors are afraid of when they consider having more than one black person on their reality show? It’s sharp cultural criticism delivered in yuks.
Racial Draft
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Show: Chappelle’s Show (2004)
Some of the “Racial Draft”’s big moments haven’t aged well: Is a past-his-prime Tiger Woods still the No. 1 pick, even during his comeback? But like many aspects of Chappelle’s Show, Racial Draft was ahead of its time. Racial identity, one of the show’s biggest themes, has since blossomed into a mainstream topic. There would’ve been plenty of material for a second edition between Rachel Dolezal’s existence, Ben Carson fumbling as a member of Trump’s Cabinet, and Juice back on the loose, but the sketch’s best moments are strong enough to stand outside a cloud of what-ifs. Take GZA and RZA excitedly being drafted by the Asians and the white commentators’ secret glee at O.J’s. last-minute transaction to the blacks, for instance.
Wayne Brady
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Show: Chappelle’s Show (2004)
The Wayne Brady Show (2001-04) introduced the eponymous host’s intense fluency in talking white to a daytime television audience. It’s easy to poke fun at, and Chappelle’s Show took the bait. In a Negrodamus bit, comedian Paul Mooney’s character said, “White people love Wayne Brady, because Wayne Brady makes Bryant Gumbel look like Malcolm X.” Brady, a fan of Chappelle’s Show, was upset about the jab, and spoke to Dave’s crew about it at the NAACP Image Awards.
So, Wayne Brady-as-Alonzo Harris was also a twisted apology. In the episode, Brady takes over the Chappelle’s Show for two-thirds of the half-hour before Chappelle returns to reveal why them hanging out isn’t a good idea: Brady’s a cop-killing psychopath and pimp (“Is Wayne Brady gonna have to choke a bitch?”). He never switches away from his safe-for-daytime voice either, adding a subtle level of menace to this bad night out.
Black Klansman Clayton Bigsby
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Show: Chappelle’s Show (2003)
The first classic character from Chappelle’s Show was a black klansman by the name of Clayton Bigsby. In a Frontline spoof, we learn Bigsby, author of N****r Book, grew up blind and was made to believe he was white because an orphanage headmistress thought it “would make it easy on him.” Bigsby assures us “just because I’m blind don’t mean I’m dumb.” He later calls a group of white kids “n*****s” after hearing them blast rap music, much to their delight.
Clayton Bigsby perversely represents someone detached from W.E.B. DuBois’ double consciousness: He’s convinced he’s white and at least one fellow bigot let him slide because he’s “good for the cause.” But in a surprise twist, black people aren’t allowed in the KKK, because heads will literally explode. That Chappelle’s Show was able to get such a concept on air in its very first episode is nothing short of a miracle.
True Hollywood Stories
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Show: Chappelle’s Show (2004)
The fact that Charlie Murphy became a star with the “True Hollywood Stories” entries speaks to how viciously funny they were. Cable television hadn’t really seen a storytelling style like Murphy’s: The Prince basketball game and Rick James beatdowns felt like hood folklore, tales where our keeping-it-real protagonist ends up in bugged-out situations—and Prince serving you pancakes after destroying your squad in a basketball game is certainly a bugged-out situation.
It didn’t matter if “True Hollywood Stories: were based on real events: Charlie Murphy’s narration made every preposterous detail stick with his street sense of clarity, especially in his episode-long recount of his relationship with “habitual line-stepper” Rick James. In this bit, Chappelle’s love of imagery intersects with his sketch comedy skills; he relishes in Rick James’ madcap hedonism and mixes a surreal flair into Prince’s signature sensuality.
Then there’s the actual Rick James coming in, with his defense for grinding his dirty boots on Eddie Murphy’s couch because he could “buy another one:”
“What am I gonna do? Just all of a sudden jump up and grind my feet on somebody’s couch like it’s something to do? Come on, I got a little more sense than that… yeah, I remember grinding my feet on Eddie’s couch.”
It’s such a big “Wait, what?” moment, the show itself rewinds and double takes to emphasize that, yes, you really did hear that contradiction.
The “best” Chappelle’s Show sketch is open to debate, but “True Hollywood Stories” had the biggest ramifications for its stars. Charlie Murphy became a legend off these two bits alone; Rick James became relevant once again right before he died; Prince… was still Prince, but he’d use Chappelle’s impersonation of him as a single cover. And you might still catch a dickhead shouting “I’m Rick James, bitch” during Chappelle’s stand-up shows, a small price to pay for creating comedy gold.
