One Of Chappelle’s Best Friends Is Trans

If you enjoy these cartoons, help me make more by supporting my Patreon! A pathetically small amount of money ($1! $2!) turns into a living for me when multiplied by a whole bunch of readers.

I’m about halfway through drawing a cartoon about city budgets, but the new Dave Chappelle stand up special on Netflix, which premiered six days ago, diverted me. Chappelle’s special was full of misogyny and transphobia, but the transphobia was perhaps more central to his show.

Chappelle closed the show with a long story about a transgender comedian he was, he said, close friends with (although he also said he didn’t know his friend has a daughter until after her death). It’s a sad story, and I’m sure Chappelle really did love his friend. But it was also a transparent attempt to excuse the transphobia of his show by saying “look, I have a trans friend!”

Normally I’d hesitate to do a cartoon about a stand-up special which most people won’t remember a few months from now. But the “one of my best friends” will, sadly, continue being relevant long past Chappelle’s use of it, so that seemed to justify doing the cartoon.

When I was a child, “some of my best friends are Jewish!” was already a cliché. And one that was obviously ridiculous – of course someone could both have a Jewish friend (or a Black friend, or a trans friend, etc etc) and still harbor some bigotry towards the group. It’s commonplace.

The “some of my best friends are _____” excuse implies a model of bigotry in which bigots are always overwhelmed with anger and hate towards whatever group they’re bigoted at. In this model, it’s impossible for a bigot to be nice to, or to feel fondness for, a _____, because apparently they can’t even be in a room with a ______ without trying to punch them or something.

But in real life, that’s not how it works. Bigotry isn’t limited to blind hatred; it can come out in more subtle ways. And people are full of contradictions, including the contradiction between being bigoted against ______ while still liking a particular ______, who is considered “one of the good ones.”

Think about how many misogynists nonetheless love their wives or their daughters.

While I was drawing this strip, I came across this wonderful response to Chappelle by Mx. Dahlia Belle, a standup comedian here in Portland.

Again Dave, some of us are Black, and when I was growing up in the midwest, there was never a shortage of racist white dudes to tell me about their Black friend, who gave them permission to say “nigger”. I hear you, Dave. I hear you holding up our fellow comedian Daphne Dorman as the Good Tranny, who never made Dave feel bad for being transphobic.

My character in this strip is based on Chappelle – both what he says and his appearance.

But I didn’t sweat making the drawings into a recognizable caricature of Chappelle, since this cartoon isn’t just about Chappelle. I just look at some photos of Chappelle and did the drawings, and figured however they came out is how they’re meant to be.

Which isn’t to say I didn’t work the drawings – but I worked, not on creating a resemblance to Chappelle, but on things like expressions and body language and finding ways for four drawings of a guy just standing there to not all be the same.

Incidentally, for me to get this cartoon done only six days after the premiere isn’t exactly a record for me – but it is much, much faster than I usually work. I sometimes suspect I’m the world’s slowest political cartoonist. (But I get there eventually!)


This cartoon has four panels. Each panel shows a good-looking black man with a shaved head – let’s call him, oh I’m just picking a name at random here, “Dave.”  Dave is wearing a gray leather suit-style jacket buttoned over an off-white tee shirt. He speaks directly to the reader.


Dave speaks to the reader, but with his face turned a little bit to one side. His expression is interested but also a little weary.

DAVE: I had a friend who’s a transgender lady. But she wasn’t like those other transgenders.


Dave now grins, speaking more directly to us, and holding out a hand palm-up in a friendly fashion, like he’s speaking with his hands while telling a story.

DAVE: When I joked about trans women’s bodies and p******s and called them “dudes” and said “yuck,” she just laughed long and hard.


Now Dave looks annoyed, looking down a bit, as he thinks of his critics.

DAVE: She didn’t criticize me or make a fuss about “pronouns” or use made-up words like “TERF” like other transgenders do.


Dave is looking at us again, smiling, arms spread wide.

DAVE: She was a good one.

DAVE: In conclusion, I had a transgender friend, so nothing I say can ever be transphobic. Take that, transgenders!

This cartoon on Patreon

This entry posted in Cartooning & comics, Lesbian, Gay, Bi, Trans and Queer issues, Transsexual and Transgender related issues. Bookmark the permalink. 

6 Responses to One Of Chappelle’s Best Friends Is Trans

  1. 1
    Mandolin says:

    Also, like, people just have different ideas of what they find joking matters.

    My mother square dances with a trans woman who makes jokes about surgery that are A) funny, and B) probably not jokes everyone would be comfortable making. I’m not going to give an example because it seems like the wrong thread.

    Of course, in that case, my mother’s friend is telling the joke *herself* and of course that makes a difference. Also, it’s not a transphobic joke, just a little audacious. But the point is it’s her boundary to draw and it doesn’t invalidate anyone else’s boundaries, nor do theirs invalidate hers.

    I suppose a different example might be that, as a Jew hanging out with Jews, sometimes someone will tell a flat-out anti-semitic joke, one of the really stupid ones you’d get in a, like, hundred-year-old Vaudeville routine. Almost always, the context is that the person telling the joke is Jewish, and that the people in the room are either all Jews or almost all Jews. But if my husband (non-Jewish) repeated the joke back to me in a similar or private situation, that would be fine. For me. But it doesn’t mean that it’s generally fine.

    Anyway. I don’t think his trans friend is doing anything wrong by laughing.* Not that you said she was. It’s just another, related point–he’s mistaken in thinking he can use one trans person as a model for all trans people.

    *He may not even be doing anyting wrong by telling *her* the jokes (IDK enough to make a statement on that)

  2. 2
    Ampersand says:

    Anyway. I don’t think his trans friend is doing anything wrong by laughing.* Not that you said she was. It’s just another, related point–he’s mistaken in thinking he can use one trans person as a model for all trans people.

    *He may not even be doing anything wrong by telling *her* the jokes (IDK enough to make a statement on that)

    I agree with all of this. There’s such a huge difference between telling jokes between friends versus telling jokes in a Netflix special millions will see. I wouldn’t criticize his friend at all for enjoying his jokes, or for saying that she enjoyed them. I wouldn’t criticize him for telling her trans jokes, as long as she was cool with it. I’d just criticize him for using his friend as a shield.

  3. 3
    Görkem says:

    @Mandolin: Out of context, so sorry if this is inappropriate, but I have always wondered

    I know there is a rich tradition of Jews joking within Jewish spaces about anti-semitism, often even making quite dark jokes about anti-semitism. And obviously many Jews are OK with this.

    But I wonder, does it ever happen that to some Jewish people, anti-semitism is too raw or too real or just not sufficiently funny, that they dislike it even when other Jewish people joke about it, even in Jewish-only spaces? Like, I can see how another Jewish person might be more acceptable than a goyim, but it doesn’t seem to follow to me that they are always sufficiently acceptable.

    Like, there’s a wide range of potential jokes to be made about anti-semitism, there’s a wide range of Jewish responses to anti-semitism, and there’s a wide range of skill levels of various Jewish joke-tellers (professional or otherwise). It seems likely to me that sometimes, these variables don’t add up to “no problem here”.

    I mention this, by the way, not to elude Amp’s point, but actually, I think, to reinforce it – if even Jewish people need to be mindful of making jokes about anti-semitism, then it definitively follows everybody else should be mindful too.

    I think that is part of the flaw in Chappelle’s thinking (to the extent that he is thinking as opposed to just lashing out) – it is very black and white and oversimplified – e.g. at one point a trans person didn’t react negatively to a joke about trans people, therefore there is a blanket, 100% license for all trans people to make such jokes, and I, a non-trans person, want that license too.

    Whereas really the lesson is that context matters, and I think trans people telling anti-trans jokes, and Jewish people telling anti-semitic jokes, have to regard context just as much as anybody else – the actual context is different, but that doesn’t mean they don’t have to regard it, it just means the calculation will often (but not, I imagine, always) come out differently.

    So really, Chappelle is not being asked to do anything trans people don’t do – he is unhappy because the outcome is often different.

    It’s amazing what a pseudo-socialist approach conservatives like Chappelle have to cultural goods (as opposed to material goods) – if one person, in one situation, at one time, had access to some cultural license, then everybody in every place at every time must equally share this license, or else a crime has been committed. (In fact, few socialists are this doctrinaire about material goods).

    And needless to say Chappelle would not be equally indulgent about a white trans person making anti-black jokes, so he’s doubly wrongheaded.

  4. 4
    Grace Annam says:

    Context matters. I have a close friend who is a Jew and the son of Holocaust survivors. Each of us has a sense of humor which includes a very dark area, and we enjoy being able to share that.

    Between the two of us, he can tell many jokes about Jewish people safely which he absolutely could not tell on a stage in front of random people. And, I’m certain there is a segment of jokes he could tell only to other Jews, and not to me. Likewise, I know many jokes about trans people. Some I don’t tell. Some I tell only among trans people, when the time is right. Some I feel free to tell in front of my Jewish friend. And there are some I would tell to a random audience, though they are a select few. But it’s perfectly possible to tell jokes about a kind of person without punching down on that kind of person.

    Here’s James Acaster, on recent transphobic comedy material.

    Here’s Steve Hughes with a brilliant and subversive bit of comedy about stereotypical gay men:

    Hannah Gadsby on gay people, not punching down one bit:

    It’s perfectly possible to do comedy about and around people without denigrating them. It all depends on who’s the butt of the joke, and at the margins, who’s the butt of the joke can turn on who’s telling the joke.

    Here’s an example of the dark humor my friend and I share: he once texted me a picture of Stalin, with the caption, “Dark humor is like food. Not everybody gets it.” He and I, in private between us, thought it was hilarious. I would not present it in most venues and expect it to be well-received, including at Alas. Also, I probably wouldn’t have sent it to him; that was probably most safely a one-way joke.

    I’ve heard Trevor Noah, who is a brilliant comedian whose material is 99+% likely to land well with me, use the phrase, when appropriate to the joke, “my nigger” (as when one Black person is familiarly talking with another). I am white, and there is zero chance that I would ever attempt to land a joke which included that phrase, or utter that phrase under almost any circumstance. It’s not mine to utter, even in service of an absolutely side-splitting joke.

    This is such a simple idea, context, that when intelligent, skilled professionals like Chapelle pretend not to understand it, I frankly don’t believe it. So Chapelle has a trans friend who laughs at his jokes. That’s great. Doesn’t mean Chapelle’s in a good position to expect random people, and especially random trans people, to laugh at his joke. It would be like me telling the Stalin joke without knowing the room really well. It’s just not going to land.

    So Chapelle has a trans friend. That’s nice.

    Now he just needs to get himself a friend who has cerebral palsy so he can start making jokes to diverse audiences about spastics! Nothing could possible go wrong with that. What a palsy career move that would be!


  5. 5
    Jacqueline Onassis Squid says:

    That Stalin joke is just fantastic. I don’t actually LOL very much when reading things but in this case I do.

  6. 6
    nobody.really says:

    The Stalin joke must be appalling, ‘cuz I really like it.

    Stalin may have killed more people than Hitler, but I might joke about Stalin in ways I might not joke about Hitler. This kind of illustrates the idea of hate crime/terrorism: The public perceives some actions as targeting a recognized group of contemporary concern. I recognize Hitler as targeting Jews, Gypsies (Roma), and other groups that recognize as being subject to group-based oppression today. Stalin killed a lot of people–but I perceive that he was motivated by a desire to maintain his own power rather than group animus specifically. Doubtless people have many theories about this–but that seems different than people’s perceptions about Hitler’s group animus.

    My sensibilities doubtless reflect my ignorance–but I would be surprised to learn that I have greater ignorance about these matters than most people.

Leave a Reply

Your email address will not be published. Required fields are marked *