Dave Chappelle Is Back to Making Transphobic Jokes at Madison Square Garden Event

Dave Chappelle can’t help himself.

At a Monday night screening for his new documentary project Untitled, and fresh off the heels of his highly controversial Netflix stand-up special The Closer, the self-proclaimed uncancelled comedian let a few more transphobic jokes fly.

The 48-year-old had a running gag about pronouns, said the f-slur, joked about claiming to identify as a woman to get a cushier prison placement, and waved off a previous declaration that he would stop making jokes about the LGBTQ+ community, saying that rule only counts when cameras are rolling.

It’s eye-roll-worthy material, seeing as how Chappelle caused an uproar in October following the premiere of The Closer that was widely condemned as being transphobic, after the streaming giant reportedly plunked down $24.1 million for the special.

It’s an eye-watering amount of cash for something that quickly turned into a PR nightmare for Netflix, and even spilled out onto the streets when Netflix employees staged a walkout in protest of the special, forcing the company’s co-CEO Ted Sarandos to issue an apology after initially defending the special. Terra Field, a trans Netflix employee at the center of the protests, announced her resignation from the streamer on Monday.

In The Closer, Chappelle defended DaBaby after the rapper went on an inexplicable homophobic rant over the summer and sided with Harry Potter author turned anti-trans activist J.K. Rowling, declaring himself a TERF—or a feminist who doesn’t believe transgender women are women and excludes them from feminism.

Dave Chappelle Says He’s a TERF and Is Quitting LGBTQ Jokes in Netflix’s ‘The Closer’

“Effectively, she said gender was a fact, the trans community got mad as fuck, they started calling her a TERF,” he said, adding, “I’m Team TERF. I agree. I agree, man. Gender is a fact.”

But a month on from the nationwide backlash, Chappelle stopped by New York City’s Madison Square Garden—one of the stops on his 11-city tour of screenings for his new documentary—and couldn’t resist smugly winking toward the controversy that just seemed to be quieting down.

In fact, he childishly snickered at his own promise at the end of The Closer, which he had made after speaking fondly of his friend, the late trans comedian Daphne Dorman, who’d previously defended Chappelle when he landed in hot water over similar transphobic material in his 2019 Netflix special Sticks & Stones.

Chappelle vowed to be hitting pause on jokes about the LGBTQ+ community until he and the LGBTQ+ community could both be laughing together again. “I’m telling you: It’s done. I’m done talking about it,” he concluded.

But on Monday night, Chappelle laughed as he acknowledged his promise to stop with that kind of material, but with the new caveat that he’d only do so if the set was being recorded, earlier pointing out that everyone in the 20,000-person arena had their cellphones locked away in Yondr pouches.

After the screening of his heartwarming documentary, it took Chappelle only a few seconds to launch headfirst into his recent troubles. “Week four of being cancelled, it’s crazy,” he began, launching into a tale about how he had to take out an order of protection against a racist neighbor who had turned up at his house a few months ago.

He described that his wife had gifted him a pearl-handled .22 caliber pistol, joking that the last thing someone would say to him before he had to use the weapon would be “f----t.” And if Chappelle did end up going to jail for murder, to escape the roughness of prison he said he would simply claim to identify as a woman.

Chappelle continued with his bit, explaining that after getting the order of protection against his neighbor, he offered to pay for his rehab or therapy, because clearly the man was not mentally well.

He said the payment would have to be kept a secret, otherwise other people with no health insurance would come knocking on his door looking for medical help, adding that trans people would be among those asking him to pay for their surgeries.

Chappelle went on to boast that he’s glad he wasn’t technically cancelled, saying he was lucky that he had been surrounded by a circle of friends, later bringing out comedian Jon Stewart, as well as musicians Fat Joe, Busta Rhymes, and Rakim.

He also made a series of pronoun jokes. When introducing the musician H.E.R., he quipped, “It’s a pronoun you don’t hear much!” Later on when riffing with Stewart, Chappelle mentioned that he’d form a transgender tribute band named “They.”

Stewart, who had just professed Chappelle's graciousness and blasted people who wanted to make money off conflict, seemed to shrug the jokes off, adding “Can’t stop, won’t stop,” toward Chappelle’s line of jokes.

Chappelle’s brief set was preceded by thunderous applause following the screening of Untitled by Oscar-winning filmmakers Julia Reichert and Steven Bognar (American Factory).

The documentary is a moving and uplifting work, already earning praise when it debuted at the Tribeca Film Festival over the summer. During the height of the pandemic last spring, Chappelle turned his tiny hometown of Yellow Springs, Ohio, into a comedic destination.

Chappelle flew in friends like Kevin Hart, Chris Rock, Donnell Rawlings, Trevor Noah, Mohammed “Mo” Amer, and David Letterman to perform at an outdoor venue for locals in his town. Michelle Wolf was also a frequent performer—she happened to be staying with Chappelle’s family when quarantine was put in place, and ended up spending months on end with them.

The documentary speaks to the spirit of community, both locally and professionally. While the comedians were able to grace the stage again and embrace one another after months of separation, Chappelle’s neighbors and those from out of town were given some much-needed laughter in such bleak and uncertain times.

Dave Chappelle Backed by Family of Late Transgender Comedian Daphne Dorman From ‘The Closer’

Plus the shows provided the town with a serious influx of cash, pumping $9 million into hurting businesses.

But for all the humility and sense of community that Untitled showcased, Chappelle’s decision to gleefully poke at a sore spot weeks after the collective disgust he caused in the name of comedy shows that he never really took the harm and outrage that The Closer caused that seriously.

A leaked version of his set in Ohio showed that Chappelle had nixed some of the offending transphobic material from the tale about his racist neighbor and still managed to gain rapturous laughter from the audience.

It’s clear that Chappelle wants to make the jokes he’s always made and push the buttons he has long pushed, no matter the backlash.

Just a month ago, someone from his team declared that “Dave stands by his art: No more jokes about transgenders until we can all laugh together. The streets are talking, and Dave is listening. At some point, when everyone is open, I’m sure the communities will come together.”

Perhaps that was just another one of Chappelle’s jokes.

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