Four Comedians On How Their Transness Has Informed and Influenced Their Careers

For most of my life, comedy has been a coping mechanism, not a career path. Even before I questioned my gender, I’d been told I was too sensitive for stand-up, that it wasn’t for people like me — until I stumbled into an open mic in 2021 and saw a queer comedian perform for the first time. When I got the courage to do standup that July, I’d only been out as trans for a year. I had no sense of who I was, let alone what kind of comedian I wanted to be.

In March of 2022, a clip I posted went viral. It was a throwaway joke from a show with two audience members: “I’m pansexual, polyamorous, and non-binary; because I’ve never made a single decision in my entire life”:


Ironically, it actually means I make all the decisions all the time #comedy #standup #queercomedy #polyam #nonbinary #pansexual

♬ original sound – Rowan Zeoli

When I posted that clip, I’d been doing standup for eight months, with less than a thousand followers. In the span of days, it got 1.5 million views and I gained an audience of 16,000.

Every day since has been more difficult than the last. Almost two years in, I’m questioning why I’m still doing comedy at all.

Being a comedian is an isolating experience, full of self-doubt and rejection. That’s why stand-up is often described using the language of war. If it’s going well you’re killing, murdering, crushing. If it’s not you’re bombing, dying, and getting buried. Being a trans comedian feels like walking alone through an active war zone, with a pink and blue target strapped to my chest. The cognitive dissonance of telling silly little jokes to strangers who may be on the opposite side of a genocidal culture war is debilitating.

Selfishly, I pitched this interview series for community and guidance — things rarely found in comedy. Clara Olshansky, Max Gross, and Kai are three of the best trans-masc comics working today. Days before this interview Kai recorded his upcoming special, Kaipocolypse Now. Max and Clara — both undefeated roast battle champions — created the only all-queer roast battle, Flamethrowers, looking to create a safe space for queer and trans comics to bully each other. I admire them all not only as writers and performers but as people. With millions of likes, hundreds of thousands of followers, hours of material, and years of collective experience between them, I wanted to know how being trans has informed and influenced their comedy careers.

I started doing standup out of a desire to be understood, to be laughed with rather than laughed at. In the last year, I’ve received comments from thousands of (mostly trans) followers saying I was the first trans comedian they’d ever seen. I felt a new responsibility. I stopped doing comedy for myself, I was doing it for them — for us. Conversely, I’ve gotten just as many comments saying people like me shouldn’t exist.

I want fans of stand-up to see the nuanced reality of being a trans comedian. More importantly, I wanted other trans comedians to know we aren’t alone. That I’m not alone. What we have to say matters, even if it feels like nobody is listening. Comedy at its core is a radical act, a weapon we have to dissect and critique the systems that rule our lives. No revolution can be done in isolation, it inherently requires community. For trans people to collectively exist on stage in defiance of those systems, and to mock their absurdity, can be as traumatizing as it is healing.

The Conversation

Max had recently talked to another comic — who is cisgender — about this contradictory experience. The comedian asked Max something I’ve thought while writing every set I’ve ever done — Why do you have to talk about being trans? For Max, it’s about controlling the audience’s perception of him. I think every good comic does this through their comedic persona, but trans people have the added consideration of how an audience perceives our gender. “If I don’t start with [being trans], I don’t pass,” Max said. “Even if I crushed and people go home saying, ‘Oh, she did great.’ I would rather them say ‘He bombed.’” I feel the same as a trans femme who doesn’t pass.

However, if I address it too quickly, the audience pulls away the moment I say trans. If I don’t address my gender at all, most audiences assume I’m a cis gay man, which is as invalidating as it is insurmountable as a comedian. If the audience and I don’t agree on who I am, my material won’t work. I have to acknowledge my transness subtly or it feels like I’m keeping some unspoken secret, a puzzle the audience has to solve before they can even listen to my jokes.

That’s why Clara also tends to start their sets with nonbinary material. ”I can’t have someone not understanding on the most basic level who I am.” When Clara started stand-up they were “working hard to be a woman” — and not succeeding in either arena, of comedy or gender. “It was hard to perform with a constant internal critic saying, ‘You don’t sound pretty enough. Clara, sound more like a girl.’”

After coming out, I catch myself with this same hypervigilance, making sure I look and act “trans enough” on and off stage. Even when I do present more femme to match people’s binary expectations of transness, I feel a disconnect between my comedic persona and who I really am. Imposter syndrome surrounding my gender presentation kept me from coming out in the first place. Now, doing stand-up, scrutinizing every facet of myself for content, has only put that under a microscope. In some ways that has helped me figure out how I really feel through all the anxiety and self-doubt. This pre-pandemic joke from Clara shows how exactly how comedy can be a catharsis for that insecurity: “I’m cis, I think. But if I heard someone say the things I’ve said in a movie, I would turn to the person next to me and go, they’re gonna come out as nonbinary before the end of this movie.”

Performing comedy about their gender provided Clara with confidence in their identity that they couldn’t get in isolation. “Being nonbinary on stage [and] talking about who I actually was, [is when] things started going a little better.”

Kai came out pre-pandemic and had conflicting feelings about his craft after doing so. Although he was being told he now looked more at ease on stage, he felt that coming out as a trans man made his comedic persona less interesting. “I became more comfortable on stage because I was more comfortable with how I existed within myself. [But] Everyone who does well in standup has a hook. Being a binary trans man is hard because now I’m just some dude. Boring! What do I talk about now?”

That led us into talking about the writing process. In the months since the video, I shifted from long-form storytelling to writing almost exclusively with Tiktok in mind. I exploited every private corner of my trans experience — regardless of how traumatic — for a twenty-second sound bite I could share with the trans people on the other side of my phone screen. It wasn’t sustainable, and it left me chronically drained. I needed them to tell me a better way was possible. Despite their large online following, Clara and Max won’t allow themselves to write material geared toward social media content. “You get the thing that you set your sights on,” Clara said. “If you write to TikTok, you could go viral on TikTok, but that’s what you’re pointing yourself in the direction of.”

I wanted to know who it is they’re writing for, if not for social media who in their mind is laughing? “My answer is not what it should be,” Clara says, before one of the most wholesome sentences I’ve ever heard. “I really just picture doing the joke at mics with our friends.” Though they might not think that’s the right answer, having that community is what has kept me going through it all. Very few people understand what it’s like to be trans or a comedian individually, and even fewer can truly empathize with both. If I can make them laugh, I know I’ve found something. Max says having a large online platform as a trans comic can be good and bad for your material. “On one hand [writing for the internet] is writing to reach other queer and trans people. [On the other] writing for a massive, faceless internet inherently comes with considering online backlash”


its mento iwness luv. one day i’ll get another tape to pull clips from but today is not that day #comedian #standupcomedy

♬ original sound – Max Gross

Kai laughed knowingly, having experienced an internet pile-on himself. “Oh no, everyone’s always gonna be mad at you.”

“I’m learning. I don’t think this is avoidable.” Max reflected on a clip he’d posted earlier that week, which went viral. While half the comments were from other trans people, the other half was filled with hate. The transphobic hate compiled at such an exponential rate, it was safer to delete the video altogether than keep the post up. Kai’s right, this is a universal experience for not just trans comics, but every person on the internet — though trans people are disproportionately targeted. Clara doesn’t even respond to compliments from people they don’t know. “I can’t have mean people seeing that I engage with comments. I just can’t open up the door to spending mental energy on this.”

After two years of responding to every comment, I’ve blocked hundreds of people and deleted countless clips trapped on the “wrong side of TikTok,” because the algorithms on these platforms have no desire to protect us. They thrive on engagement, regardless of what that engagement is. Each time this happens, I feel trapped.

Do I keep the video up so trans people can see themselves in comedy while subjecting myself and them to the onslaught of transphobic hate? Or do I preserve my own mental health and delete a high-performing video, damaging my career, robbing trans people of representation, and allowing the transphobic trolls to feel victorious? This emotional danger can become very tangible during a live set. Max told a story of something that’s happened to every trans comic I’ve met. While he was doing his set, the “People at the front table were having a very unhappy conversation about [my] identity.”

When I asked how the comics have navigated this, Kai offered genuine advice I’ve been given by every successful marginalized comedian I know: Get Funnier. “If it’s a good enough joke, even if people don’t like you or agree with you, they’re still gonna laugh.” If it sounds like harsh advice, it’s because you haven’t been a comedian. Though it’s starting to change, stand-up comedy is largely an unforgiving boys club dominated by white, cishet men who only laugh at their friends, if they laugh at all. While I want my comedy to be for trans people, there is no stronger validation of my craft than when I force a group of transphobes to laugh in spite of themselves.

Max emphatically agreed, turning his wrist to show the word UNDENIABLE in bold American Traditional lettering. “I got this tattoo after my first time headlining. I don’t just have to be good to get people on my side, I have to be undeniable. My jokes have to be so good, even people who fundamentally disagree with who I am as a person still laugh.”

Even just getting stage time is difficult for any marginalized comic who isn’t trying to appeal to a cishet white audience. The success of a stand-up comic largely depends on how much an audience can relate to their experience, which is easier when you share identities with most of the audience. It’s not just transphobes though, I’ve had some of my worst shows in front of supposedly liberal audiences. I think the politicization of transness, and how comedy has been weaponized against it, has made many well-intentioned allies idealize us as brave, inspirational victims rather than what we are: comedians. Max, who is also chronically ill, resents how dehumanizing being an inspiration can be. “I would rather be funny than inspirational.” Kai experiences this from white audiences as a Black trans man. “When people clap after a joke. I’m like, oh God.”

I’ve found that regardless of how much a liberal-leaning audience supports transness in theory if they aren’t at least a little queer, many won’t laugh at all. Having a queer or trans audience is a precious gift. You don’t need to waste minutes of your set with a quick Gender 101 course. Just having trans people in the audience can change the entire dynamic. Clara shared a joke that gets a different response depending on the Kinsey Scale of the crowd: “I used to be so worried people weren’t gonna see me as enough of a woman. And then I came out as nonbinary and I learned, no, people see you as a woman.” When Clara tells that to straight people, they usually get silence and sympathetic awes. “When I tell it to queer people, they laugh.”

Audiences who get it all are few and far between. Even for those who do, there’s so little representation, trans comics often get forced into being a monolith for the trans experience. As artists, we use our marginalized identities to inform our work, but we shouldn’t be required to speak for anyone’s perspective besides our own. I craft material with the intention of sharing my experience with other trans people and educating cis people about trans issues, but I shouldn’t have to. If and when we do decide to speak on them, we shouldn’t be held to unreasonable standards, especially by members of our own community. Kai urges not just cis audiences, but younger trans people, not to view individual comics or public figures as the representative for all trans experiences. “Being trans is a very private experience [that] we make very public through comedy. The entire conversation is still relatively new. A lot of young people don’t understand the [trans] experience has nuance. Different people are coming at it from all types of places. Just because your experience doesn’t mirror theirs, doesn’t mean one of you is doing it the wrong way.”

As we were nearing the end of the call, Clara offered me a gift — a full-circle closing thought. “I’ve talked about how my transness informed my comedy,” they said. “I haven’t really talked about how my comedy informed my transness.“ Before coming out, comedy helped Clara build confidence, even if they weren’t sure the feelings behind the material would make sense to other people. “Having people laugh was huge for feeling secure in my identity. Which is maybe a bad take,” Clara joked. “You should feel secure in your identity, even if you’re not funny.”

It was a perfect conclusion, but I was reluctant to end this conversation I’d so desperately needed. In my two years of comedy, I’d only ever had a handful of conversations like this, and none so honest about how painful being even a marginally successful trans comedian can be. It was healing to find other people who understand what it means to love comedy, even if comedy is hesitant to love us back. This is my community. This is who I do comedy for. I don’t know if I found an answer on how to make it easier. I don’t know if it will ever be easier. If nothing else, even if it was just for an hour, we got to laugh about a world we’d only ever tried to suffer through alone.

The conversation continues in Part Two, where Rowan speaks with three femmes on the celebrations and expectations of being a trans woman in comedy.

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Rowan Zeoli

Rowan Zeoli is a journalist from Brooklyn, New York. Her work covers the intersections of gender and niche counterculture, and can be seen in Polygon and Tripsitter, among other publications.

Rowan has written 4 articles for us.


  1. My favourite comedian DeAnne Smith’s latest show-in-progress is called Nipless. They talk about their top surgery. It’s great to watch them grow as a comedian and as a person over the years while talking about different very personal topics (like their sick rack). It makes them more relatable and likable so I’ll keep following their shows. :)

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