Dave Chappelle’s recent Netflix special touches deeply on transgender topics and provides personal insights into his experience coming to terms with transgender people. This article will analyze and respond to this introspective journey into Chapelle’s worldview.

Trans people have existed in varying forms in every culture throughout the course of human history. Dysphoria has always been a part of the human condition.

It’s something that all people of all these cultures have had to come to terms with, and for many, it isn’t an easy bridge to cross.

Dave Chappelle said of us, in his special The Age of Spin, “They’ve got the longest mental gap to bridge.”

This comment, as well as a few other offending jokes in both this special, and the next which followed, Deep in the Heart of Texas has stirred up controversy in the media and in various trans/transactivist communities.

Personally, I thought both specials were hilarious and would recommend Age of Spin especially.

Here’s a thing about comedy:

All comedy transgresses.

By its very nature, comedy is an act of transgression. Either your expectations are transgressed as a clever comedian subverts them, your senses are transgressed as something comedic teases at them, or your personal life is transgressed in such ways that highlight relatable things you can look at in a different way after a comedian shuffles them about and reorders them to their own subjective liking.

Comedians walk this fine line of transgression in all of their work. At any moment, any thing they say and/or do could cross the line drawn between comedy and offense into dangerously transgressive territory.

As it turns out, though from my perspective, Chappelle’s above specials were quite good and transgressed without offending me, he did offend a lot of other trans people.

In Chapelle’s next special, Equinamity, he spoke to this experience:

But motherfuckers are just taking it too far. I don’t know why or how everybody got this goddamn sensitive. You know who hates me the most? The transgender community. Yo, yeah, these motherfuck– I mean, I didn’t realize how bad it was. These motherfuckers was really mad about that last Netflix special. It’s tough, man. I don’t know what to do about it ’cause… ‘Cause I like them. Always have. Never had a problem with them. You know. Just fucking around.

As he mentioned in his previous specials, Chappelle genuinely does not seem to be any sort of transphobe. He has built the bridge required to cross the mental gap he mentioned in Age of Spin and he has accepted us as a part of culture he doesn’t have a problem with. As such, he’s incorporated us into his comedic transgressions.

Equanimity, the word Chappelle employs in the naming of this special is defined as follows by Merriam-Webster:

Chappelle strives to maintain this equanimical balance in his transgressions as he works his way through many of the uncomfortable discussions western civilization currently faces.

A matter fact, I think I make fun of everybody. I mean, as a group of people, they have to admit that… it’s kind of fucking hilarious, man. I’m sorry, bro. It’s like… I’ve never seen somebody in such a hilarious predicament not have a sense of humor about it. They’re born feeling like they’re something other than they’re born as, and that’s… That’s kind of funny. I mean, it’s funny if it’s not happening to you.

I have long been of the mind that the world desperately needs transgender comedy. Preferably from a mainstream transgender comedian, but I think Chappelle’s voice is a good start. He’s absolutely right. Our predicament is hilarious, as most all human predicaments are. If we are so stressed in our predicaments that we can’t step back from them to allow a comedian to transgress upon them and make us laugh, then we have a problem.

And there’s the rub, transgressing upon the current transgender predicament can be a detriment to us if we aren’t equanamical. We trans folk suffer such horrendous attacks on our equanimity, that when a comedian transgresses upon it, any boundary they might cross risks causing distress.

From my own perspective, I greatly appreciated Chappelle’s specials because I am equanimical. I’ve had a wonderful life and for me, transition has been nothing but an uplifting, life-affirming, stress-free experience. My family, friends, co-workers, and communities have all accepted and embraced me as who I am. I’ve never once suffered any sort of serious conflict over gender identity with anyone in my life.

Online, sure, but I purposely seek out those conflicts myself in engagement with transphobes.

All-in-all, I have a great life and am not burdened by any form of stress centering on my gender post-transition.

Others aren’t so lucky.

For others, to transition is to suffer the slings and arrows of social outrage. It would have likely been the same uplifting, life-affirming, stress-free experience that it has been for me, but something went wrong for them.

Maybe the people in their lives rejected them. Maybe their social support structure collapsed. Maybe they lost access to the medical or psychological care they needed. Maybe they’ve fallen into poverty or even homelessness. Maybe they’ve been assaulted or abused.

Anything could happen.

Ours is not an easy road to travel.

However, in spite of the sensitivity I have to the feelings of trans people with regard to comedy, I do feel that Chappelle fields the topic well, because he turns the topic inward, and gives his audience a personal introspective of his own life’s journey in coming to terms with transgender people.

Chappelle continues:

It’s like that white black bitch that’s in the news all the time. Rachel Dolezal. She always says that. She– She– She was– She’s a white woman, but then she dressed up like a nigga and… shot her way up to the very top of blackness. And I always wanted to meet her just so I can understand. I just wanted to have dinner with her, so I can just look in her eyes… and call her a nigga to her face. What the fuck is that bitch talking about? “I identify as black.” That is trans-talk, lady. Stop biting. Stop biting. There’s a big difference between her and a trans. The difference between her and a trans is I believe transgenders . I don’t understand them either, but I know they mean what they say. Them niggas cut they dicks off. That’s all the proof I need. Never seen somebody just throw their dick away. Don’t need it. I don’t understand, but I believe you, and I support your decision, motherfucker. But how far is Rachel willing to go? Hmm? What is Rachel willing to do so that we blacks can believe that she believes she’s actually one of us? Bitch, are you willing to put a lien on your house? So that you can invest in a mix tape that probably won’t work out. She didn’t even change her name. Didn’t even change her name. Her name is Rachel. I can’t believe in that name. You want my support , you gonna have to change your name to the blackest shit I’ve ever heard. Bitch, you gonna have to change your name to Draymond Green. I don’t know a blacker name than that. That shit is black on paper. If you type “Draymond Green” in the Airbnb… that shit will log off automatic.

I’d like to, first of all, speak to Chappelle’s main point here, which I believe is to show that there is a big difference between identifying with a gender and identifying with a race.

Race is an arbitrary marker of culture.

It very much makes sense for people to appreciate and identify with cultures. It doesn’t make sense for people to identify as a race, because race is only an arbitrary marker of that culture. Sometimes cultures close themselves off, which is understandable, but in most, everyone can participate in and appreciate culture in spite of race as long as it’s done out of respect and with the purest intent.

Changing your skin color really doesn’t change any of that. It’s probably not going to gain you any sort of cultural acceptance. In fact, it runs you at great risk of cultural rejection.

So, when Chappelle criticizes Rachel Dolezal by saying, “That is trans-talk, lady. Stop biting. Stop biting. There’s a big difference between her and a trans.” I agree, but by completely different logic.

There is nothing physiological about feeling like another race. In fact, I’m not convinced a race is something anyone can feel like at all. Races are skin pigments which arbitrarily indicate culture.

Sexes are very different biologies with different physiologies and differing sensual, social, psychological, and emotional experiences of reality. I couldn’t live as the sex I was born into, so I’ve done everything to minimize it and live as a transwoman.

Aside from differing impacts by outside influences and perhaps an internalization of heritage, can it really *feel* that different to be another race? If so, would these feelings ever create such distress in someone as to disrupt function and necessitate a racial transition?

I’m skeptical.

Though I am open-minded.

If you disagree, I’d love to hear your opinion.

People get mad, bro. People get mad about everything I say. I was doing a show. I was in Portland, Oregon. And I was checked in a hotel under the name Charles Edward Cheese. I came back to my room late at night… and there was a note. It was like a letter on my desk. It was addressed to “Mr. Cheese.” So, obviously, I’m gonna assume that whoever wrote this letter must be an intimate friend. This is not some kind of name that a person would just guess. But then I open the letter, and it turns out I don’t know this person at all. It’s a fan letter. I’m not even used to the idea that I have fans, but I’m grateful for it. And… And even though I’m grateful for fans, I… I don’t read those letters. Be nice if I did, but realistically, it’s like, “What am I, Santa Claus, nigga? I don’t have time for this. Got shit I wanna do. I’m trying to chill.” Read all these dreams and wishes from strangers. But then– But I read it. I’d already opened it, so I just read the whole letter. And you know what, man? Whoever wrote this letter truly loves me. I mean, they were really fucking nice in the letter. And then they described to me what it was like to come to the show. How excited they were and how much fun they were having. And then they said… that when I got to my jokes about transgenders … that they were quote, “devastated.” ‘Cause turns out that whoever wrote the letter was transgender . I’m gonna be real for a second. As a policy, you gotta understand, I never feel bad about anything I say up here. And I would never admit this to you if I hadn’t locked your phones up. But it was the weirdest thing, like when I read this letter… the shit made me feel bad. I didn’t feel bad about what I said, you understand. I felt bad that I made somebody else feel bad. But I feel like… I feel like it was probably… this joke I’m about to tell you right now.

Chappelle rebounds from the empathy and introspection above and goes on to tell an unapologetic joke about Caitlyn Jenner, which I’ve spared you in this text. I’d personally never heard of Jenner prior to her transition and I don’t have feelings one way or the other over her. The thing that bugs me is just that people have for some bizarre reason crowned her queen of the trans people.

Chappelle shares his perspective as someone who knew Jenner prior to transition. As such, her transition was a shock, as it was to many, to his worldview. It’s almost traumatic to some degree, certainly for atheletes who may have at one point idolized or positioned Jenner as a role model.

It’s a lot to come to terms with for some.

I can see how someone could see this joke as terribly offensive, but my takeaway is that Jenner’s shock to Chappelle’s worldview was the beginning of his journey to coming to terms with transgender people and, ultimately, he worked that out via comedy.

I don’t know what I said that upset that person. But I’m gonna tell you something. When I read that letter… in the moments after I read it, I did something that many black men in America do not have the time or the money to do. I thought about how I felt. Asked myself a very basic question that I don’t think I ever directly contemplated. I said, “Man, Dave, if you’re writing all these jokes, do you have a problem with transgender people? ” And the answer is absolutely not . The fuck you guys think I am? I don’t understand all the choices that people make. But I do understand that life is hard, and that those types of choices do not disqualify you from a life with dignity and happiness and safety in it. But if I’m honest… my problem has never been with transgender people . My problem has always been with the dialogue about transgender people .

Chappelle makes great points above and I will let them speak for themselves.

He continues, to make some terrible, but true, points:

I just feel like these things should not be discussed in front of the blacks. It’s fucking insulting, all this talk about how these people feel inside. Since when has America given a fuck how any of us feel inside? And I cannot shake this awful suspicion that the only reason everybody is talking about transgenders is because white men want to do it. That’s right. I just said that. If it was just women that felt that way or black dudes and Mexican dudes being like, “Hey, ya’ll, we feel like girls inside.” They’d be like, “Shut up, nigger. No one asked you how you felt. Come on, everybody, we have strawberries to pick.” It reeks of white privilege. You never asked yourself why it was easier for Bruce Jenner to change his gender than it was for Cassius Clay to change his fucking name?

My main criticism of Chappelle’s position here is that black people transition too and he seems to have forgotten about them in the framing of this statement.

However, the rest of what he says does have a ring of truth to the dark heart of America and I believe Chappelle’s apparent lack of empathy for those of his own race who transition is a symptom of that very issue.

DISCLAIMER: I am not anti-capitalist, though what follows here and elsewhere in this article explores criticisms to capitalism. Critique of capitalism is not anti-capitalism.

Where Chappelle remains wrapped up in racism with a twinge of transphobia in forming this idea, I point my finger to capitalism, where the blame belongs.

If the most privileged among us didn’t want to transition, transgender people would never be accepted in capitalist society.

It shouldn’t be that way.

Everyone should have access to the care they need and all of our concerns toward those cares should be considered equally in a Democracy.

Capitalism has stifled Democracy.

Figures like Jenner carry much more weight in public consciousness than anyone else ever could because capitalism has deemed it so.

It’s about time we had a reigniting of Democracy in America.

And if I were to be brutally honest… the only reason I ever have been mad at the transgender community, is because I was at a club in LA and danced with one of these niggas for six songs straight. I had no idea. Then the lights came up and I saw them knuckles. I said, “Oh, no!” And everybody was laughing at me. WorldStar. I said, “Why didn’t you say anything?” Then I heard that sultry voice. “I didn’t say anything, Dave Chappelle, because I was having a wonderful time. And I wasn’t sure how you’d feel about it.” I said, “You knew how I’d feel.” And she said, “I’m going home. I don’t want any trouble from you.” I said, “Home? It’s only two songs left. I mean, we might as well… finish the night.” And we ended up having breakfast together. Oh, grow up. That doesn’t make me gay. I just titty-fuck them. Those titties are as real as any titties in LA. It was two o’clock in the morning. I was just borrowing a little friction from a stranger. Whoops! It’s the madness of youth. It’s the types of mistakes a man makes when he’s young. I wouldn’t even know that it’s necessarily a mistake. It was a wild night out. But I don’t do it like that anymore.

Remember, this is an introspective journey Chappelle is taking us through. He expresses transphobia comically here, but he expresses it in reflection on his past self, which he acknowledges to be foolish.

His past self’s transphobic reaction to the woman he was dancing with, however, is one that I would like to speak to.

For Chappelle, who had at that time in his life not yet come to terms with transgender people, the experience of not knowing, but enjoying his time with a transgender person was quite a shock for him.

The experience Chappelle relays here is a microcosmic view of an experience I have had in entirely different, non-sexual contexts, with many transphobic people in my own life.

In the majority of my career, I have never disclosed the fact that I’m transgender to any employers or co-worker but in moments of my choosing. I’ve also worked with a great many people and customers in both my life’s work and my career who have appreciated my efforts on their behalf and have never once called into question the validity of my womanhood.

I have always just been Ella to these people.

In many moments, I have known exactly how someone might feel.

I have encountered a great deal of transphobia in my life, but none of it has ever been directed at me. It’s always something I overhear, directed at no one in particular, or at someone else.

Often, I never come to know someone holds those sorts of feelings until after I have known them and/or worked closely with them for a year or more.

This leaves me in a powerful position to combat transphobia, like the woman Chappelle danced with, I’ve just had a wonderful time helping others in my career and I choose to not share the fact that I am transgender with most along the way because I don’t know how anyone will feel and I don’t feel it demands mentioning.

It’s scary every single time, but my reaction to encountering such external transphobia is to come out to the person expressing transphobia.

Such experiences have a healing effect over transphobia.

Again, I have only ever been Ella to such people, a hard working, respectable woman.

The idea that I could be anyone else is impossible for them to grasp.

They consider this, and it re-shapes their thinking.

Because the truth is, having known me as they have, the idea that I could ever be a man is foreign to them.

They realize that if I were to “de-transition” and would become a man, this would invoke a similar negative reaction in them to the reaction they would have if they’d known me in the first place. They would have to begin using a new name and new pronouns. The process would be exhausting for them and they would be equally inclined to not participate.

My coming out in this way tends to bring transphobes to terms with transgender people.

As I said, this is a scary thing to do, but I would encourage any trans person lucky enough to find themselves in the types of positions I’m describing to do as I have done when you encounter external transphobia among those with whom you interact with regularly.

It can work wonders.

In Chappelle’s comedy, he relays this experience well, through the lens of sexual comedy.

He shows himself encountering and then overcoming transphobia to finish the wonderful night he was having with the trans woman he’d met and he scolds his audience for any notion that might form that this is a homosexual act.

Chappelle is not gay, he’s had straight male interaction with a transwoman.

His view here says all we need to know about whether or not Chappelle is transphobic any longer.

Chapelle ends his special with this:

You know, I’m gonna give you a history lesson , ’cause I’m sure this wasn’t on your entry exam. But every naturalized American has heard something about what I’m about to tell you. Picture, it’s the early ’50s in the United States. This 14-year-old boy goes down… from Chicago to Mississippi to meet his extended family for the first time. He’d never been to Mississippi. And before he went, his mother said to him, very pointedly, she said, “If a white man looks you in your eyes in Mississippi, look away.” And I don’t know what you know about black people from Chicago, but they’re not a scared people. Legend has it, he was in front of a convenience store, hanging out with his cousins, having a good time, and a white woman walked out of the store, and he thought she was pretty, and he said… [wolf whistles] “Bye, baby.” Not realizing that he had just made a fatal mistake. Four days later… Four days later, a group of adult white men burst into this family’s home and snatched a 14-year-old boy out of bed, in front of his family that was powerless to stop them, and he was never seen alive again. His name was Emmett Till . They found his body maybe a few days later. It was in a creek, tied to a wheel so it would sink, horribly beaten and bloated. Hideous. And lucky for everybody in America… his mother was a fucking gangster. She was. If you can imagine , in the very midst of a mother’s worst nightmare, this woman had the foresight to think about everybody . She said, “Leave my son’s casket open.” She said, “The world needs to see what they did to my baby.” And every publication here in the United States, from Jet magazine all the way to the New York Times, had this boy’s horribly bloated body on its cover. And if our Civil Rights Movement was a car, this boy’s dead body was premium gas. This was a very definitive moment in American history, where every thinking and feeling person was like… “Yuck! We gotta do better than this.” And they fought beautifully, and here we all are. And the reason that I bring that up tonight and why it’s relevant now, is because less than a year ago, the woman that he allegedly whistled at… admitted on her deathbed… that she lied in her court testimony. And you can imagine, when we read that shit, we was like, “Ooh! You lying-ass, bitch.” Was furious. That was my initial reaction. And initial reactions, we all learned as we get older, are often wrong or more often incomplete. They call this phenomenon “standing too close to an elephant.” The analogy being that if you stand too close to an elephant, you can’t see the elephant. All you see is its penis-like skin. You gotta step back and give it a better look. And on stepping back and thinking about it for a few moments, I realized that it must have been very difficult for this woman to tell a truth that heinous about herself at any point in her life. Even the very end. And I was grateful that she had the courage to tell it before she left this world. Because it’s an important truth and we needed to know. And I said to myself, “Well, thank you for telling the truth… you lying-ass bitch.” And then time goes on, and then after time, you can kind of see the whole elephant . And it’s humbling. ‘Cause you realize that this woman lied and that lie caused a murder. But that murder set in motion a sequence of events that made my wonderful life possible. That made this very night possible. How could this be that this lie could make the world a better place? It’s maddening. And that’s how I feel about this president. I feel like this motherfucker might be the lie that saves us all. Because I have never felt more American than when we all hate on this motherfucker together. Jesus Christ. It’s good. And when it happens, I can see everybody that’s stuggling. So if I’m on stage and I tell a joke that makes you want to beat up a transgender , then you’re probably a piece of shit and don’t come see me anymore. Or if you don’t understand that when a football player takes a knee during the national anthem, he’s actually standing up for me, then you might not want to fuck with me anymore. ‘Cause I swear no matter how bad it gets, you’re my countrymen, and I know for a fact that I’m determined to work shit out with y’all. And if that woman that said that heinous lie was alive today, I would thank her for lying. And then I would kick her in the pussy.

Chappelle tells the story of Emmett Till, who died a tragic death after 21-year old Carolyn Bryant claimed the then 14-year old Till made sexual advances toward her.

This led to Till’s kidnapping and brutal murder and his mother showed the world what the racists had done to her child.

In Carolyn Bryant since confessed that the accusation she made against Till, which led to his death, was false.

Rosa Parks is said to have had Till on her mind in December 1955 when she refused give up her bus seat in Montgomery, Alabama, kickstarting nationwide protests.

The killing has been the subject of a play by the Nobel laureate Toni Morrison, it has inspired a myriad of stories, poetry by Langston Hughes and Gwendolyn Brooks, Elizabeth Alexander, Jericho Brown, and even a song by Bob Dylan.

This lie, which sparked this horrific tragedy, led, somehow, to such great healing for our nation.

Chappelle ends by tying this to President Trump, calling him, quite aptly in my opinion, “The lie that saves us all.”

Donald Trump, with his air of capitalism has become a symbol for the people to unite against.

A common capitalist adversary to overcome.

And I have seen it spark Democracy the likes of which I haven’t seen in America in my entire life. The kind of Democracy I’ve only heard stories about from times before I was born.

It feels so good to see Americans being American again.

We are coming together.

We are finding common ground.

We are becoming a Democracy again.

We all know the truth of Donald Trump’s campaign slogan isn’t that he is going to Make America Great Again™, it’s that we are, in uniting to face the adversary of Democracy.

Chappelle closes with slaying a few adversaries of his own, in calling out any transphobe who might read a hateful message in his comedy and later unleash it as abuse against a transgender person.

He tells it like it is.

He shows us the whole elephant.

They aren’t worthy of his transgressions.