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Dave Chappelle at Radio City Music Hall

Source: Kevin Mazur / Getty

Dave Chappelle has rarely been known to hold back when it comes to his comedy routines. His fans usually come to him for hilarious and thought provoking commentary on race, as well as other political issues. However, it appears there’s one subject where Chappelle is dropping the ball, LGBTQ issues.

On Tuesday, Chappelle released two new comedy specials to Netflix as part of a reported, $60 million three-special deal. According to New Republic, the specials are filled with laughs, but also many cringe worthy moments concerning gay and transgender people.

In the special, Chappelle often uses a stereotypical high-pitched, over-enunciated voice when speaking as a gay man. He also insists gay people “always have some kind of political argument.” He gives the example of an argument he had with a gay man who was petitioning to have the words “husband” and “wife” removed from marriage licenses. Chappelle argues, “N*gga please, save me the semantics.” He continues, “Take your chips out of the casino, you’re about to crap out. Go outside, talk it over amongst yourselves, and whichever one of you is gayer, that’s the wife.”

Chappelle also puts transgender issues under an ill-informed and often transphobic microscope. He says things like he “misses” Bruce Jenner and he reduces gender assignment surgery to a joke about how strange it would be if he and his friend decided to go to a hospital and “cut their dicks off.” He even acts offended when someone corrects his pronoun usage, as if it’s such a strain for him to refer to transgender woman as “she.”

An intersectional lens is also missing when Chappelle mentions, “Black dudes in Brooklyn, hard, street motherfuckers, who wear high heels just to feel safe.” He insinuates the public is more ready to protect transgender women than they are Black men. It seems he missed the news of transgender women of color (a lot of them Black) getting killed at alarming rates. Safety for them is very limited.

There’s a thin line between a joke laughing with a group and in support of a group, as opposed to a joke laughing at a group. It seems Chappelle is laughing at when it comes to LGBTQ issues, which can be linked to layers of homophobia, transphobia and misinformation. Sadly his approach is not surprising considering his history of problematic LGBTQ jokes. A better understanding of queer and trans issues could be beneficial to the comedian…or just don’t talk about it at all.