Dave Chappelle still doesn’t understand transgender people, but he’s ready to support them

Dave Chappelle in a formal suit during a performance

Note: Smartphones and recording devices were not allowed at the show. All the quotes in this story were either written down by hand by the writer or come from a Vulture piece on an earlier show. As a result, some quotes may be slightly paraphrased.

Dave Chappelle faced backlash after making an off-color joke about transgender people in his Netflix comedy special, which debuted March 21 as part of a two-part series.

“If your best friend pitched [gender reassignment surgery] to you, you’d be horrified.” The comedian continued:

“Yo, nigga, let’s go to the hospital and cut our dicks off and make pussies out of them shits.” “What?! Can’t we just get matching jackets or tattoos or something? You sure that’s what you want to do?” “There’s only way to find out, nigga. Wu-Tang! Pow! Pow! Let’s go to the club and trick niggas into fucking us. Yeah.”

Chappelle’s joke perpetuated a longstanding myth about trans women — that they go to nightclubs to trick men into having sex with them, presumably by pretending to be “real women.” Despite the backlash — BuzzFeed noted that Chappelle’s sense of humor hadn’t evolved with the times, and Mic’s Jamilah King suggested his “masculinity is fragile and in constant need of affirmation” — the comedian never apologized for the bit.

But if Chappelle’s latest run of live shows are any indication, he’s done some soul-searching since then. His new material, which he’s performing as part of a 14-night run at New York City’s Radio City Music Hall, includes a lengthy section devoted to trans issues. It’s clear that Chappelle is still more confused by trans people than he is sympathetic to their experiences. But it’s also clear that he sees why people were upset by his words — and that his views on the subject have evolved since the Netflix special.


At the beginning of his set Aug. 9, Chappelle warned that he had a “diabolical joke” in store, but would not reveal it until later, when the audience liked him more. About a third of the way into the show, he segued into a riff on President Donald Trump’s announcement that he would ban trans people from serving in the United States military.

“I was shocked that there are transsexuals in the military,” Chappelle said, “but there are 6,000 troops ... it’s actually a great idea ... imagine if you’re in ISIS and you see a soldier with a beard and double-D boobs running at you.”

After a few more one-liners, Chappelle ended the joke by soberly proclaiming, “Let them fight.” The rest of the bit followed a similar structure — veering from crude, transphobic humor to more thoughtful statements that demonstrated, at the very least, a willingness to engage with the trans experience that was missing in his Netflix special.

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Later, Chappelle noted that “transsexuals are as brave as any of us. Probably braver.” He added, “I don’t understand them, but I believe them because they cut their dicks off. That’s all the proof I need.” The comedian also addressed the Netflix controversy, albeit indirectly, describing a letter he received from a transgender fan who said they were devastated by the joke he told (he claims to not know which joke they were referring to).

“When I read that, it made me feel bad,” Chappelle said, admitting that his first instinct was to ignore the letter entirely. Instead, he explained, he thought about the issue more before concluding that his fan’s feelings were just as valid as his own. Chappelle’s gut instinct may still be to laugh off trans issues, but he seems to have made an effort to change that.

As for that “diabolical” joke he announced at the beginning of the set, Chappelle ended up taking a shot at Caitlyn Jenner — not much of a risk these days, considering the heat she’s gotten for supporting Trump.

”I read in the paper that Caitlyn Jenner was contemplating posing nude in an upcoming issue of Sports Illustrated, and I knew it was politically incorrect to say, so I figured I’d just say it for everybody: yuck,” he said. “Fuck, man, I just want to read some stats. Like, why are you cramming man-pussy in the middle of the sports page like that?”


Soon after, Chappelle ventured back into less contentious territory. “I don’t have a problem with trans people,” he said. “They have a right to make those decisions if they aren’t hurting anybody else.” Unfortunately, he closed by arguing that the trans rights movement only gained widespread attention because white men are affected by it. This may be a valid point — but it’s poor justification for the reductive approach he’s taken to trans issues in his comedy.

“My problem has always been with the dialogue around trans people,” Chappelle said. “All this talk about how they feel inside ... since when has America given a fuck about how anyone feels inside? ... The only reason all of us are talking about transgenders is because white men want to do it. If it was just blacks and Mexican like, ‘Hey, y’all, we feel like girls inside,’ they’d be like, ‘Shut up, nigger, no one asked how you felt.’”

All told, it might not be the most evolved perspective on trans rights. But for Chappelle, who’s clearly still struggling to understand the issue, it’s a start.