Caitlyn Jenner is targeted by comedian Dave Chappelle in his new, transphobic set

On Tuesday night, comedian Dave Chappelle kicked off a series of 16 shows at Radio City Music Hall in New York.

Chapelle is known for controversial humour, particularly surrounding race, but he reportedly took it to a whole new level when he decided to tackle the hot topic of transgender rights.

According to a Vulture review of the show by Jesse David Fox, Chapelle spent the first 20 minutes of the set discussing trans issues.

Fox said the jokes were “rooted in disgust and generalisation.”

Chapelle discussed Trump’s recent ban on transgender people in the military, saying he was shocked because he hadn’t realised there were any transgender service people.

“Sounds like a secret weapon to me,” he said.

Dave Chappelle (Photo by Jason Merritt/Getty Images for GQ)

“If I was in ISIS in the trenches fighting against the United States and all of the sudden I see a man with a beard and big D-cup titties just rushing my foxhole and s***, I’d be horrified.”

He then seemed to go in another direction as he told a story about a fan letter which had contained criticisms of his transphobic jokes, saying “it honestly made me feel bad that I made somebody else feel bad.”

The empathy didn’t last long however, as he went on to tell the very joke he had been criticised for, despite saying that he was aware that it was “politically incorrect”.

He began: “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.

“F***, man, I just want to read some stats, like why are you cramming man-pussy in the middle of the sports page like that?”

He then changed tack again, saying that although he doesn’t understand transgender people, he doesn’t think that “disqualifies them from being a human being that deserves a life with dignity and happiness and respect,” to which the audience clapped.

But having barely allowed the applause to die down, Chappelle proceeded to argue that trans issues are only relevant to white people – despite the fact that black women are disproportionately targeted for transphobic violence.

Related: Black trans woman killed in the US is the 16th recorded this year

“The only reason all of us are talking about transgenders is because white men want to do it,” he told the crowd.

“If it was just blacks and Mexicans like, ‘Hey, y’all, we feel like girls inside,’ they’d be like, ‘Shut up, n*****, no one asked how you felt.’”

This is hardly the first time Chapelle has offered his take on LGBT issues.

Last November, in a set at the New York comedy club, The Cutting Room, Chappelle offered up his opinion on the much-debated bathroom bill.

“If you need to show your birth certificate to take a dump at a Walmart in North Carolina, that’s insane.”

But, he, of course, felt the need to add quickly that he wouldn’t want “a woman with a d***” using the urinals next to him.

He also demonstrated that he has no understanding of intersectionality, lashing out at LGBT activists.

“They should not be having that conversation in front of black people,” he said.

“You go ahead and feel something about your rights. But if you’re putting sexism and homophobia and transphobia in front of racism, you should be ashamed of yourself.”