The Uncompromising Politics of Dave Chappelle

Last Friday, NBC announced that Dave Chappelle would be hosting a very special episode of Saturday Night Live on Nov. 12. The unpredictable comedian’s first ever SNL hosting gig, accompanied by musical guest A Tribe Called Quest, felt like a miraculously timed mirage—the promise of something beautiful on the post-election horizon. Of course, nothing about this presidential election has been easy, or simple. From the unprecedented rise of Donald Trump to campaign-threatening email complications, this election has revealed the worst that America has to offer in a never-ending race to the bottom. Given the morally murky landscape of 2016, Dave Chappelle is perfectly suited to host SNL, come a Clinton presidency or Armageddon.

In the year of the political renegade, Chappelle is a fittingly loose cannon. Like many Americans, his chief political allegiance seems to be to the pity-party of general dissatisfaction. In a surprise standup set the night of his SNL announcement, Chappelle raged against both presidential candidates, devoting a large portion of his 60-minute set to attacking Hillary Clinton. The comic essentially blamed Clinton for releasing Trump’s infamous Access Hollywood tape. “What I heard on that tape was gross,” Chappelle said of the leaked 2005 audio featuring Trump’s unofficial motto, “grab them by the pussy.” “But the way I got to hear it was even more gross. You know that came directly from Hillary,” he said. Like the Trump campaign itself, he seemed more concerned with the former secretary of State and the media’s agenda, as opposed to the actual content of Trump’s remarks. “Sexual assault? It wasn’t. ‘And when you’re a star, they let you do it,’” he said, quoting Trump’s leaked boast. “That phrase implies consent. I just don’t like the way the media twisted that whole thing. Nobody questioned it.”

Although he copped to voting for Clinton early in his home state of Ohio, he told the audience that he didn’t “feel good” about it. “She’s going to be on a coin someday. And her behavior has not been coin-worthy,” he reportedly said. “She’s not right and we all know she’s not right.” Chappelle appeared to praise Trump, calling him “the most gangsta candidate ever”: “They asked him how he knows the system is rigged and he said, ‘Because I take advantage of it.’ He may as well have flashed his membership card for the Illuminati right then.”

Chappelle’s relationship to the media, much like his relationship to fame and to his own fans, is complicated. At Chappelle’s Show, Dave was a pioneer in tackling race relations through comedy. Sketches like “Frontline: Clayton Bigsby” and “The Racial Draft” are as important and precariously positioned today as they were in the early aughts. Somewhere between observational humor and slapstick and between comedy and tragedy, Chappelle was one of the first mainstream comics to find the funny in the discussion of race and blackness in America. Like anyone who is doing important, nuanced work, Chappelle worried about the way his comedy would be perceived, and feared that his political perspective would be misinterpreted. Out of context, his show ran the risk of perpetuating the very stereotypes it was parodying.

This fear became a reality in 2005, when Chappelle abandoned his own show. The comedian later described a disturbing incident in which he was filming a skit about a pixie who appeared in blackface. “There was a good-spirited intention behind it,” Chappelle recalled. “So then when I’m on the set, and we’re finally taping the sketch, somebody on the set [who] was white laughed in such a way—I know the difference of people laughing with me and people laughing at me—and it was the first time I had ever gotten a laugh that I was uncomfortable with. Not just uncomfortable, but like, should I fire this person?” He added, “That concerned me… I don’t want black people to be disappointed in me for putting that [message] out there... It’s a complete moral dilemma.”

Chappelle’s decision to abandon his eponymous project and escape to South Africa at the height of its success was obviously a controversial one. And the comedian’s subsequent insistence on shirking the spotlight, refusing interviews and all but entering early retirement increased his reclusive mystique. Even as Chappelle’s upcoming SNL debut seems to signal a more substantial comeback, the comedian is falling victim to the kind of misinterpretation that pushed him out of the industry in the first place. In the wake of his Friday night set, the Jared Kushner-owned Observer really leaned in to the comedian’s anti-Clinton comments. The Observer’s account of the set—recording devices were not allowed in the room—was headlined “Dave Chappelle Defends Trump, Rips Clinton,” which Chappelle’s camp quickly dispelled as a mis-categorization. According to a representative for the comedian, “Dave is disgusted by the tone of the election and especially by the idea that his comedy would be misconstrued to defend Trump.”

“Jesus Christ, I’m not a Trump supporter,” Chappelle later told TMZ the Monday before the election. “Unequivocally, no. I’m not gonna elaborate on it. Hell, no. Just everybody vote, for whoever you want to vote for. But that’s not what I’m doing.” In reference to the outlet that mischaracterized his standup set, Chappelle rolled his eyes: “It was from the Observer,” he said, with special emphasis on the newspaper’s name. “Just come see my shows for yourself and don’t listen to conservative newspaper reviews.”

Indeed, Chappelle has been upfront about the fact that this round, he’s with her. In early October, he offered a decisive take on the two candidates. “I hope everybody votes. I know it’s a tough decision,” Chappelle told the audience at the Roots Picnic festival. “Hillary Clinton versus white Malcolm X. That crazy carrot-top head motherfucker is gonna kill us all.” But Chappelle’s on-the-record support for Clinton obviously didn’t stop his unexpected tirade from making headlines. If anything, the pressure of fame has gotten heavier since Chappelle described himself as “allergic” to the hyper-scrutiny of show business. With the comedian already under the microscope for speaking out, is history threatening to repeat itself?

Given that he had already cast his vote for Secretary Clinton, Chappelle’s decision to cast doubt on her campaign just days before Election Day was a confusing one. Then again, the comedian has made an on-again, off-again career out of refusing easy categorization and palatability. From being booed off the Apollo stage to mocking his own audience, Chappelle’s comedy can be hard to swallow. But as unexpected as his comments on Friday seemed, Chappelle has always been a political comedian. In fact, for a comic whose career has been marked by the unpredictable, Chappelle’s outspoken politics may be the most consistent thing about him.

In the summer of 2015, Chappelle didn’t hold back on the question of the artist as political activist. Addressing a philanthropic crowd in Long Island, he insisted, “This is a very surprisingly emotionally charged time, so people like me, I think, are very relevant and necessary in sorting through all this information and emotional content... And when we are at our best, hopefully we are doing a great service to many people... The biggest enemy of an artist is apathy. A kid gets killed by the police and I buy a T-shirt and before I can wear that one, there’s another kid (killed) and I’m running out of closet space.”

Chappelle does his “great service” as he always has—by using humor to bring important issues to the forefront, albeit in an unconventional way. In August, he declared at a rare performance in New York that Black Lives Matter is a “terrible slogan”: “It’s like naming gum ‘Chewy.’ It’s obvious.” After warning his audience that his would be a “racist show,” he said he preferred the phrase spearheaded by Dwayne Wade, “Enough is Enough.” This prompted Chappelle to call out Donald Trump once again. Responding to the nominee’s ill-advised Twitter attempt to use the shooting of Dwayne Wade’s cousin as an appeal to back voters, Chappelle offered an all too prescient retort: “Oh, yeah, now I’m voting for Donald Trump.”

Chappelle has opined on presidents and presidential candidates before, through his own unique lens. His “Black Bush” Chappelle’s Show sketch argued that a black version of the president would have endured far more scrutiny. It was the kind of political commentary that only Chappelle could do, simultaneously taking on racism and a host of the former president’s more questionable judgment calls in the lead-up to the Iraq War. Additionally, the basic premise that a black president would face an unreasonable amount of flack became eerily relevant once Barack Obama took office. President Obama himself reportedly considers Chappelle’s Show “one of the greatest shows of all time.” And Chappelle—who once joked about being “starstruck” by a phone call from the president—has shown that the respect is mutual, and was in the audience at Obama’s final concert at the White House.

From 2003 to 2006, Chappelle’s Show pushed the thorny topic of race relations into the pop culture zeitgeist. As the man behind it, Chappelle has earned his reputation as a deeply influential, relentlessly political comic. But if Hillary Clinton wins on Tuesday night, his subsequent SNL debut will be a reminder that, in this race, there’s no such thing as a clean victory. Chappelle’s apparent belief that he voted for the lesser of two evils doesn’t make him a traitor, it makes him Dave Chappelle—restless, complicated, and constantly questioning. If Hillary Clinton comes out ahead come Election Day, Chappelle’s hosting gig will represent the political struggles and dissatisfaction that won’t disappear in the wake of that vital win.

As a man with less-than-glowing things to say about Clinton and, more importantly, about the direction that this country is heading in, Chappelle is a reminder of the America that Clinton could inherit. Immediately, there’s the issue of the constituents who doubt her honesty and will likely deride the system that helped elect her as rigged—concerns that Chappelle seems sympathetic to. And then there are the issues that Chappelle has called attention to for over a decade: race in America, the African-American experience, and the black body count. As the host of an SNL episode that will hopefully be imbued with joy and relief, Chappelle is not a predictable or an unproblematic host. But the problems he has raised, and those that he continues to grapple with, are important ones. Agree or disagree with his politics, but you have to admit that Dave Chappelle starts conversations worth having.