Within the span of a brutal 20 minutes early on in the first special, The Age of Spin, taped in Los Angeles, Chappelle jokes about a superhero who has to rape women to save lives and then goes into an extended bit about a transgender colleague who evokes all of the most vile stereotypes associated with trans people. This woman is big, bullish, frightening and commands attention by throwing her anatomy on the conference room table during meetings.
Chappelle's jokes are always profane, sometimes funny, and deliberately offensive. They're also crystal clear examples of how transphobia actually works.
Transphobia, like other crippling fears, says absolutely nothing about the people it's aimed at. It says everything about the person who's aiming it. In the parlance of today, Chappelle's masculinity is fragile and in constant need of affirmation. This isn't unusual. This is how masculinity actually works. The only thing people fear more than what they don't know is what they do know, which is that their gender is a carefully created construct, enforced and re-enforced by aggressive and sometimes violent policing by families, communities and the societies in which we all live. People who dare to step outside of these constructs may be liberating themselves, but they're also exposing the lie that we're all taught to believe from birth, which is that sex and gender are the same, linear, unchanging rocks of identity.
People born black and assigned male at birth have it especially tough. They are both desired and feared by white folks, and are punished severely for showing any signs of deviance. At times during his specials, Chappelle walks this very thin line with ease. In the second special, Deep in the Heart of Texas, filmed in Austin, he jokes about being hit with a snowball and called a "nigger" by a group of white teenagers who wind up being arrested and taken to a police station. When one of the boys' mothers approaches Chappelle apologetically, saying that her son wasn't raised to be a racist, she pleads and asks what they can do to teach him a lesson. His answer? If she gives him a blowjob. It is absolutely a sexist moment, but he's almost daring the audience not to laugh with him. And it's an especially dangerous bit for a black man to perform in a Southern state on stage before a predominantly white audience, where deep-seated taboos still exist about sex between black men and white women.
Chappelle is telling the world, perhaps even without knowing, that black masculinity exacts a huge toll on the people forced to perform it every day. He tells us this when he talks about his gay friend from high school who asks him for marriage advice, to which Chappelle can only mumble, "Well, nigga, I don't know, I mean, you gay." What he's also saying to that friend is this: you've made the decision to go step outside of what's acceptable for black men. I haven't. You deal.
All of this isn't to say that I wasn't disappointed by much of what I saw in Chappelle's comeback. I expected more. But my disappointment isn't necessarily with Chappelle, but with my own expectations of him. I'd expected peak Dave Chappelle a la Comedy Central's Chappelle's Show, with its brilliant moments like the racial draft, or Clayton Bigsby, the black white supremacist. Stand up is a different format, this is a different era. Sure, it wasn't only roughly 10 years ago that Chappelle's humor was seen as defiant and progressive. But in the intervening years since he's been away from the public spotlight, the audiences around him have matured.
Today, there are more nuanced representations of gender — and the people who transgress it — than ever before. If you want to see a measured portrayal of a transgender woman, look no further than Laverne Cox's portrayal of Sophia on Orange is the New Black. If you're looking for smart, nuanced comedy, check out D'Lo, a Sri Lankan-American comedian and actor who's been performing for the better part of two decades.
Put simply, things change. Unfortunately, Dave Chappelle's approach to gender hasn't.