Early in Dave Chappelle’s two-part comeback special on Netflix, he alludes to a rift between himself and the black community. “I was supposed to be in Flint, Michigan, for a charity benefit that was supposed to raise awareness for the appalling condition of the water in Flint,” he begins. He goes on to explain to the crowd at the Hollywood Palladium — many of whom likely weren’t particularly aware of the crisis — exactly how dire the straits are for the predominantly African-American residents of the town. Then, he explains why he didn’t show up: Chris Rock invited him to the Oscars.
“Come on, man. What am I gonna do about that water? I’m not a superhero. I need to have fun,” Chappelle says in the tag to the joke. As one of the few people who can say they’ve attended the Academy Awards, I almost understand where he’s coming from. Did you know the bar is open the entire show? You’d be in awe of the sheer number of sliders you can eat at the Governor’s Ball. Also, if you’re lucky, you might stand in line behind Gary Busey, like I did. It’s truly a magical wonderland of everything that makes people love (and hate) Hollywood. I get it. It’s just that Chappelle’s no-show at a Flint fundraiser came the same year as the notorious #OscarsSoWhite protest movement, which throws his choice further into question. It’s one of those purely self-interested decisions that people who live here in L.A. make every day. What’s remarkable is that Chappelle admitted it in front of a camera.
We want our comedians to be brave, to tell the truth, and to be vulnerable. This has been the default setting for stand-up for at least a decade, if not longer. Marc Maron, Louis C.K., and other comedians of their generation are lauded for laying bare their most painful truths, and audiences happily pay money to see it. Pete Holmes’s new HBO show, Crashing, is another in a long line of half-hours that mine the often lonely lives that comedians are forced to live in order to achieve their career goals (not to mention it’s his own biography). We want to see the noble loser, the downtrodden schlub, or the plucky underdog. But what happens when a comedian is no longer quite so plucky?
Some famous comedians have found a way to stay relevant past the point where they’re so rich, they never have to step in a grocery store again. Kevin Hart and Louis C.K. are probably the best examples of comedians who can still connect with their audiences on a deeper level despite massive success. But what often happens to comedians at this stage of their career is something I call Eddie Murphy Syndrome — the condition in which a comedian ceases to be relatable. Murphy left stand-up not long after he became an internationally known movie star. The last of his pair of concert films, Eddie Murphy: Raw, was released in 1987, the same year that Beverly Hills Cop II came out. Raw was vintage Eddie — energetic, profane, and supremely confident. The ease with which he slipped in and out of characters remains awe-inspiring. It was also misogynistic and homophobic, aspects of his performance that the mainstream hardly flinched at at the time.
A year earlier, Murphy, starred in The Golden Child. By 1998, he was Dr. Doolittle. What he wasn’t anymore was a stand-up comic. We never saw Eddie joke about his high-profile run in with the law in 1997, nor his multiple marriages or string of box-office bombs. He hasn’t performed in almost 30 years, and he seems unlikely to do so now. It could be argued that he’s making the right choice, because whatever we loved about Eddie then is not who Eddie is now, or at least who we want him to be. He’s the kind of guy whose problems are not our problems. To a lesser extent, Chappelle is dealing with the same situation, except in his case, we’re actually witnessing what happens when a comedian returns to the stage after many years away.
In his Netflix special, Chappelle’s rhythm and cadence are still there. When he was on the rise, his act was almost never overtly political, and when he did touch on sensitive cultural issues, like poverty in America’s inner cities, it would often be through a surrealist lens, like his famous drug-dealing-baby bit from Killin’ Them Softly, his classic 2000 HBO special. Then, there’s his skewering of white people, which was taken to its limit when he donned whiteface for multiple episodes of Chappelle’s Show. As comic Hampton Yount joked on Twitter, Chappelle is still the best at the “white-guy voice.” He’ll always be the Rick James guy, the guy who got high and bombed during his last comeback tour, the guy who quit Comedy Central, the guy who was so disturbed by the reaction to his TV show, he disappeared to Africa.
It should be no surprise that Chappelle’s sense of humor hasn’t changed. What has changed, however, is his audience, and their expectations of him. What we thought of as funny 15 years ago may not have aged very well — just look at the critical reaction to Chappelle’s views on the LGBTQ community. But what Chappelle is not, and has never really been, is a Chris Rock–level social satirist, or a comic like Richard Pryor who put his darkest secrets on the stage for all to see. What fueled his initial popularity was his ability to speak across cultural divides by just being funny. In his time away from stand-up, we have grafted some outsize expectations onto an artist whose first taste of mainstream success was a stoner comedy called Half-Baked in which Bob Saget asks a crowd if they have ever offered sexual favors in exchange for marijuana.
Hoping that he’d evolve or become “woke” the way people half his age are, is pointless. Chappelle is a celebrity — an aging celebrity, at that. He’s not quite in the same place as Murphy — Chappelle never had a movie career, let alone one that would push him to chase Oscars — but he is in the period of one’s life where it’s more comfortable to settle into who you are than to try to reinvent yourself. Dave Chappelle probably doesn’t have any trans friends. He’s probably not in any hurry to try to make some, either.
But he’s still a stand-up comic, which means he’s required to be honest, even when it’s ugly and unpleasant. The honest Dave Chappelle is going to tell you he doesn’t understand the LGBTQ movement, he thinks people who identify as queer are just confused, and that he’d rather go to the Oscars than Flint, Michigan. Like many other pundits, I couldn’t bring myself to enjoy his attempts to mine humor out of the struggles of trans people in America, but that’s sadly the truth of how he feels.
The successful person’s form of honesty is not the same as every other comic’s form of honesty. In fact, it might be construed as obnoxious, out of touch, and prejudiced. Much of Chappelle’s special seems ripped from a 1990s idea of life, mixed with surreal show-business moments like a recurring bit about running into O.J. Simpson. Make no mistake about it, that Flint water crisis bit was not meant to be flattering. He’s the type of person who, like me last year, hears that the Oscars have an open bar and can’t say no. In that sense, he’s still relatable. Chappelle’s most difficult task — which is true for every comedian of his generation — is to thread the needle and make his fans understand a lifestyle they have no ability to truly comprehend. With the Oscars bit, we could project our narcissism onto him and chuckle at the shared humanity of such a poor decision. But when Chappelle projects his comic gaze toward the rest of the planet, I can’t help but see him as an alien.
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