What if people had sex with monkeys? What if a Leave It to Beaver family had the last name Niggar? What if the United States held a racial draft? Dave Chappelle’s very best comedy trades in hypotheticals; through colorful stories and physical humor, the comedian creates vivid alternate realities that make the truths about our own world — ranging from criminal-justice inequality to the plight of being the only black dude on The Real World — more stark.
This weekend on Saturday Night Live, Chappelle will have the chance to do it again, with his first appearance on a sketch-comedy show since Chappelle’s Show went off the air a decade ago. But a lot has changed in 10 years. We’ve now experienced two through-the-looking-glass political moments that would have been (and largely were) worthy of parody up until the moment they actually happened: the election of Barack Obama, the first black president, and Donald Trump, the first reality TV one. How can Chappelle wring humor out of a world that has come to resemble his exaggerated sketches?
“Black Bush,” the best Chappelle’s Show skit of all time, gives a hint of what to expect. Like a lot of Chappelle’s greatest work, “Black Bush” is an inversion of cultural norms first, and an exaggeration second. Instead of using the kind of cliché you’d find on BET’s Comic View — “What if the president were black?” — Chappelle asks, “What if this president were black?” The skit debuted in April 2004, a similarly perilous time for the United States; the war in Iraq was mutating into a monstrosity, and George W. Bush had recently endorsed a constitutional amendment banning gay marriage. Chappelle took these precise policies and parroted them through the mouth of a brash, vulgar black man.
What was once stately is rendered ridiculous. “Black Bush” has some hilarious physical gags (who among us hasn’t wanted to bail on a tough line of questioning?) and clever one-liners (“Stankonia says they’re willing to drop bombs over Baghdad”), but the skit is brilliant for what it says about its audience — and, by extension, the electorate. By placing Bush’s aggressive, hateful, and buffoonish policies in the voice of a black caricature, they become pure fantasy. Chappelle is not saying, “George Bush is dumb,” which was well-trodden SNL territory by ’04; he’s saying, “You would never let a black man get away with being this dumb.” The live-studio laugh track agrees.
He was, of course, right. President Obama is generally measured and thoughtful when he speaks, the exact opposite of the Black Bush persona. But critics insisted Obama was arrogant or too professorial or, when the facade of political decorum slipped, uppity. Joe Biden once called him “clean” and “articulate,” highlighting the burden of low expectations (a mind-set Chris Rock gleefully eviscerated in his own bit about black presidents). Behaving in Obama’s dignified manner is not a requirement of the presidency — we certainly know that after Tuesday — but you won’t ever find an actual black presidential candidate saying things like “touching on each other’s titty balls.”
Which brings us to President-elect Trump, who, in his own bizarre way, is Black Bush incarnate. The Chappelle character insults women, threatens global allies, and is openly combative with reporters. These are all things Trump has been known to do; the actions even raise his standing in the eyes of some supporters. Trump is more like Chappelle’s caricature of a black president than the actual black president is. Our new inverted reality sounds like a Chappelle’s Show punch line — the kind that might cause Dave to give a legitimate belly laugh and then say, “This racism is killing me inside.”
“Black Bush” is the last sketch on the last episode of Chappelle’s Show that the comic had full creative control over. It marks the end of a two-season run that still feels like it must have lasted longer, given how profoundly it shaped the way we talk about race. There is a generation of young black people who found a way to verbalize their place in the world through Chappelle’s goofball-veiled takedowns of American institutions. (Your fave Key and Peele could never.) The show’s worldview is echoed on shows like Atlanta, in which Black Justin Bieber channels Black Bush, and online, where black kids responded to bad acoustic covers of “Formation” with #TrapCovers of all the songs they still sell on CDs at Wal-Mart.
Since the end of the show — and even as the show was ending — Chappelle’s comedy has focused on his own inner turmoil, trying to reconcile his moral code with his megacelebrity. (You know why this conflict defines him already: Comedy Central wanted to pay Chappelle $50 million to do two more seasons of his show; instead, mid-production of Season 3, he left the country and never completed another episode.) A sketch from the unfinished Season 3 about Dave’s newfound wealth sees a Chappelle companion actually die due to the comedian’s greed. But Chappelle is too self-aware to deify himself as a creative martyr — even he doesn’t know if it was smart to leave that money on the table. “The only difference between having $10 million and $50 million,” he said in a 2014 interview with David Letterman, “is an astounding $40 million. … My friends will try to make me feel better, but no one’s been through that. … They’ll be like, ‘Dave, at the end of the day, you still have integrity.’ Well, you know, great. I’ll go home and make my kids some integrity sandwiches.”
Chappelle’s inner conflicts manifest in political contexts as well. I saw him at a comedy festival in 2013, when he was just coming out of a long reclusive period following his show’s abrupt conclusion. He told long, twisting stories, and because Chappelle is both incisive and charismatic, he pulled it off. One tale was about his struggle to support Obama when he knew he’d probably face higher taxes. “That’s what it feels like to be me,” he said. “I work all my life to make some money. Finally my dreams start coming true, and all of a sudden a black president comes out of nowhere and goes, ‘Come on Dave, let’s be responsible.’ … I just got this money!”
On the eve of his Saturday Night Live appearance — possibly his highest-profile political moment to date — his feelings appear to be similarly torn. We already know he likes neither Trump nor Hillary Clinton, as evinced by a headline-generating stand-up set last week in which he heavily criticized Clinton, even though he voted for her. That’s not actually much of a shock; throughout his career he’s expressed a deep cynicism for conventional power structures, ranging from the White House to the police to, obviously, Hollywood. I doubt we’ll see much love from him for Clinton, or self-righteous anger toward Trump. Chappelle’s not going to preach to America about how royally it fucked up, but he might help people understand how the past several days have looked from a black person’s perspective. It’s one of his greatest gifts, and one the country desperately needs right now.
What I’d really love to see is another one of Chappelle’s classic racial inversions. At the Roots Picnic in New York last month, the comic called Donald Trump “the white Malcolm X.”
It’s an absurd comparison — sort of true on its face, which is funny, but so profoundly untrue due to America’s history that it becomes even funnier. The way you interpret it says more about you and your racial worldview than it says about Chappelle, which is the effect of many of his best jokes. I doubt SNL’s producers have the stomach for it, but I’d watch the five-minute sketch version of this idea. (I also live to see Dave Chappelle in whiteface.) America feels like a scary place right now, but that’s never stopped Dave from laughing before.