When J.K. Rowling came forward and took an unequivocal stance against transgender people, she drew a line in the sand that made her a social pariah to a large group of people and a martyr to seemingly even more. As her bigotry became more pronounced, I was so incredibly relieved not to have been heavily impacted by Harry Potter as a kid. The sting of having someone who was important in the creation of something you found beautiful growing up being tarnished by clear, unabashed disdain and hate, is a difficult burden in an age where it feels like we have less and less to enjoy or look forward to.

In the age of “cancel culture,” I’m not someone who immediately throws out a person because of their beliefs. I try to measure everything into something resembling fairness; but being a trans woman, I have a pretty confident read on what is simple ignorance and what is blatantly transphobic. So, most people would be surprised by how long I’ve been overlooking many comments made by one Dave Chappelle.

I will not sugarcoat this: I thought Dave Chappelle was the greatest who ever lived. As a teenager, I had seen Killin’ Them Softly and For What it’s Worth dozens of times. I own all of Chappelle’s Show and used to love showing it to friends. Dave Chappelle wasn’t simply a genius, I thought he was the funniest man on the planet and had nothing but respect for him and his craft. He had a talent of telling you stories that were not even a little bit true, yet he kept you hanging on every word. The most preposterous, silly stories were made compelling by the pictures he painted and the characters who inhabited them. The story of the homeless man taking over a bus by jerking his dick around is maybe the funniest thing I had ever heard as a teenager, and that level of funny was radiating off of him all the time. Which is why I want to tell you why, after over four years of continual disrespect towards trans people, it was this newest special where he fully lost my support. As sincerely as I can stress, it broke my heart.

It truly clicked for me that I was transgender in 2016. I was 22, a senior in college, and I was slowly learning about who I really was, piece by piece. After a long night of work on my senior thesis project, I was eagerly champing at the bit to watch the first new Chappelle special in well over a decade. I sat down with my friend, both of us totally stoked. It was in these new specials that he started making jokes at the expense of the transgender community. The way I looked at it, the only jokes that really disappointed me were ones that made me feel bad about myself; it was a twinge I didn’t fully understand. Still, they weren’t enough to fully sink my enjoyment of the special as whole, which I still found fairly funny.

I enjoyed all four of his specials that year. It was hard not to respect someone giving so much comedy in such a short period of time. In Equanimity, he first addressed the existence of a backlash from trans fans. Because I liked him, I believed him when he said it hurt his feelings that he hurt fans like that, and he made a point to say that he thought everyone deserves respect, regardless of how they choose to live their life. With this, I was willing to reach an understanding. He just didn’t like being told he couldn’t make jokes at other people’s expense, and honestly, I agreed with that! I didn’t think anything was truly off limits as far as jokes go; as most comedians feel, it lives and dies by whether or not the material is actually funny, and while I don’t think he ever batted a thousand when he talked about trans people, I didn’t always hate every trans joke he told. They didn’t all feel like they were dripping with hatred (though I should mention that I was yet to even begin transitioning in a literal or spiritual sense).

At this point, I’m sure a lot of you are thinking, “Sounds like you ignored the writing on the wall and now you’re shocked? That’s your own fault, dumbass.” And you know what? Yeah, I probably should have known better. I certainly picked it up with Rowling early on, but I was letting being a fan still stand in the way. That’s on me. But really, this piece isn’t for those who already hate him. Rather, I really want to reach all of the cis people who still agree with Dave Chappelle, the people who don’t think trans people are above ridicule, and would find most people whining about jokes in need of a backbone. I want to explain why I was wrong for giving him that pass, and what you need to understand about what he’s actually doing when he expresses his opinions about what is and isn’t funny about trans women.

I was still a fan of his when Sticks and Stones, his 2019 special, included more jokes at the expense of trans people. At this point, I was living as a woman full-time and had come a long way since the last time I watched his specials. I still thought he had some decent jokes. I thought he was leaning a little hard into the “woe is me” act regarding criticism, along with feeling like he was kicking a dead horse with all his jokes still at the expense of trans people, especially after three specials full of that same material. Even still, I didn’t want to throw the baby out with the bathwater. This time, however, I was a bit more ashamed of actually admitting I was still a fan, which was probably a decent tip off now that I think about it. I really didn’t want to believe that my favorite comedian was transphobic. He had said he wasn’t, and I told myself, “He makes fun of everyone.”

Unfortunately, it only got worse. Chappelle became more acquainted with Joe Rogan, a much more bluntly transphobic comedian with a much wider and active audience, thanks to his podcast. I was losing faith in my guy. I still believed he had wisdom to share, but I was starting to feel less welcome in his comedy. In Redemption Song, a short vignette where he talks about the current events involving the January 6th riots and the continued hypocrisy this country has for how they treat black Americans, he briefly mentions how ridiculous it is that people care more about pronouns than fixing oppression. It’s a fallacious remark that draws a line between being trans and being black, without considering how many black trans people he erases in that statement. Needless to say, it was feeling quietly hostile.

When I heard there was going to be a new Chappelle stand-up special on Netflix this week, I knew watching it would do me few favors. I also knew that if he was going to say anything about trans people, I wanted to hear it from him; I’m not a fan of having opinions on these kinds of subjects without having heard it myself. As the closing credits rolled, I knew I was no longer a fan of Chappelle. Despite all the lead up to this moment, I honestly felt betrayed.

There’s a lot of things Chappelle has to say about trans people in The Closer, but when you listen to what he’s saying, it’s all the same shit he’s been repeating for four years now. I am speaking solely on the trans material here, because this is something that most cis people really don’t understand where trans people are coming from. Many would agree that any joke that’s actually funny is forgivable. There were a couple jokes that got a laugh out of me despite how I felt watching this whole thing, because he actually made a joke in those moments. Being trans is a hilarious conundrum to live under, and there are absolutely jokes to be had at our expense. The thing is, the understanding many cis people have of what is funny about trans people, is, by nature, incredibly dehumanizing to who trans people fundamentally are, and this is Dave Chappelle’s biggest crutch.

It’s also very important to note that when Dave Chappelle wants to talk about trans people, his target is most often trans women. It’s white trans women he seems to take issue with, but he once again pays literally no attention to the idea that a trans woman can be black, or any other race, and taking them out of the equation makes it very easy for Dave Chappelle to trivialize the trans experience while ignoring the intersection of trans and racial identity.

Yes, Chappelle believes that no one is above ridicule, and to consider otherwise is to make yourself into a victim. But when you listen to the jokes Dave Chappelle has written about trans women, they all boil down to the same punchline time and time again. Chappelle thinks it’s really funny to call trans women men, to misgender and deadname us, and to express ridicule over the validity of a woman born with a penis. He thinks this behavior is playful and harmless, but he fails to understand how fundamentally dehumanizing trans women feel to be reminded of the truth that we are all acutely aware of. Chappelle will say he respects anyone’s right to live a happy and healthy life, but it’s not more important than his need to broadcast that trans women gross him out, or to say whatever else he wants about them. We are now at an impasse on what is considered “funny,” and “the GOAT” doesn’t want to hear the other side.

In the third season of Chappelle’s Show, Chappelle walked away from a 50 million dollar deal from Comedy Central after it had occurred to him that the success of the show, and the underlying message of his comedy, was being misunderstood by the masses; specifically, shitty white people. Chappelle has a story of performing a sketch for an upcoming season, and he noticed a crew member found one moment in the sketch particularly funny that Chappelle thought signaled something was wrong. Dave felt this painted a picture of a large portion of the population taking his comedy the wrong way. His actions had consequences, and he wanted to make sure he was doing this show for the right reasons. That was one of the moments that led to him disappearing from public life for over a decade.

I’ve been thinking about that story a lot, because in The Closer, Dave wants to mention that while he’s making fun of trans people, he really does sympathize with them. He talks about the bathroom bill in North Carolina and how he sincerely believes that to be cruel. He mentions that it makes trans people go to the bathroom of the gender listed on their birth certificate, and as he says this, someone audibly cheers for this law. Dave sincerely replies, “No, that’s not a good law. That is a mean law.” I do appreciate that he made sure to have his viewpoint understood in that moment, but Chappelle needs to understand that most people aren’t getting what’s a joke and what isn’t. Those lines of what’s funny are getting more unclear to them. The platform he currently has is doing zero favors to trans people, when his defense is followed up with another joke about how grossed out he is at the thought of a woman with a penis sharing a bathroom with him.

Even trying to say he’s setting a bad example feels too low-key for what Chappelle does in The Closer. He spends a little over half the special aimed directly at transgender people. He mentions the way JK Rowling has been demonized, and talks about how this taught him what the term “TERF” means (Trans Exclusionary Radical Feminist), a word Dave Chappelle describes as “a made up word trans people use to win arguments.” It’s a thoughtlessly uncharitable read on a word that describes a very hateful group of people. He immediately follows this up with, “I’m team TERF.” This was the point I started to cry. I genuinely couldn’t believe this was something he actually said during a comedy special.

Here’s the thing: there’s a big part of me that believes Chappelle has no idea how much division he’s sowing with his words here, because all of these jokes are laced with lines about wanting to love everyone, and how he has no hatred in his heart. I’m sure he doesn’t understand that he’s aligning himself with an incredibly hateful group of people who want to completely erase trans people out of public life entirely. To proudly proclaim to be a TERF is something that should be as shameful as calling yourself a Trump Supporter in 2021, something that even Dave has shown regret over after asking people to give Trump a chance shortly after he was elected.

I had trouble watching the screen after Chappelle made that statement. His jokes then started to focus on “trans women are encroaching on women’s spaces.” These were moments Dave was trying to tell his “hard truths,” and the crowd gave him thunderous applause. It left me appalled, a feeling I never wanted to feel during a stand-up performance. I loved Chappelle because he was someone whose humor brought people together, but after the same old joke about how he could clock trans women for their masculine features, he just sounded like a hack who ran out of material years ago. I realized I was beginning to hate Chappelle, and knowing that was how I felt destroyed me inside.

My brother managed to see him live less than a month ago, and at that point I would have said I was jealous; I was sure that a live performance was something worth seeing. Now, I couldn’t care less. My dream of seeing him live one day evaporated like it never existed. Dave Chappelle broke my heart with this set. He showed that he had no interest in changing where his heart lies, and I’ve talked to enough people like him where it’s easier to let them go than to continue holding out hope. It will only lead to more hurt.

One piece that will be brought up a lot from this special is his story about Daphne Dorman, a trans comedian Chappelle befriended in 2019, who was mentioned in Sticks and Stones. Dorman killed herself shortly after the special aired. I truly believe Daphne was someone Chappelle enjoyed being around; he has a whole story of how she bombed when she opened for him in San Francisco, and how afterwards, he had a conversation with her where she was very happy to answer all of Dave’s personal questions he genuinely wanted to know about trans people. After expressing some lingering confusion over the basic fundamentals of her transness, she finally loses patience and begs him, “Just believe I’m having a human experience,” which Dave says actually clicked for him.

While Dave seems genuinely moved by this act, he makes sure to mention that he didn’t hear anything about respecting pronouns, or how he wasn’t a bad guy, and that was all he wanted to hear. Afterwards, he was still allowed to make her the butt of the joke and misgender her whenever he wanted, which it sounds like she really didn’t mind. From what Chappelle has said, this is one of the only trans people Dave actually got to know as an individual. He never reached out to anyone for understanding after he first got hit with backlash. He never thought to get in contact with his trans peers in entertainment and understand why what he was saying got under the skin of trans people; he just waited until the answer worked in his favor. And all my love to Daphne, It’s absolutely terrible how she died, but one incredibly patient trans woman isn’t going to redeem Chappelle. Not now, not ever.

Dave Chappelle is not going to be doing many Netflix specials for the foreseeable future. He makes that clear from the beginning, so he’s making sure he gets in all his licks for a while. Before saying that he wants a truce from all LGBTQ people (he makes fun of the acronym in this request), he asks for empathy from both sides, despite refusing to listen to anyone who asks him to be better than he is. It’s incredibly telling that by the end of his special, one of the sorest subjects of this whole 35+ minute bit is how sad he was for Kevin Hart when homophobic jokes from Hart’s stand-up took away his chance to host the Oscars. To Dave, this is a deeper injustice than anything he can do or say about a trans person. He ends his set saying he will never make another joke about a queer person until he knows they can all laugh together. This is a very empty compromise coming from a man who would rather be seen as transphobic than pull back on one set of jokes.

Many comedians now are on the defense about their material being considered offensive, and almost all of them choose to take on victimhood than listen to constructive criticism. I thought Dave Chappelle was smart enough to realize he was hurting people, but when you’re called the greatest of all time at his age, you can get stubborn. I guess he isn’t the GOAT anymore, he’s just another sad, old man feeling sorry for himself. What a waste.

If you would like to learn where you can do some good by trans people, please check out the following resources:

Some statistics on the real-world impact of dehumanizing anti-trans rhetoric: