Throughout my teens, Dave Chappelle was my favorite comedian. This is easier to admit than it might seem: As a child, my favorite comedian was Bill Cosby.

My father had a worn VHS copy of Bill Cosby Himself, and would sit my brother and I in front of it. That’s because Cosby was “clean,” meaning the worst swear it contained was “asshole.” We watched it so often that some of the bits — which, I’m pained to admit, remain hilarious — are burned into my memory.

I didn’t decide to take a stand-up comedy class as an act of contrition, necessarily, but I am aware this is an inauspicious origin story. If I ever decide to pursue comedy as a career, I’m going to have to invent one with less-problematic early influences.

This essay isn’t about them, though. I didn’t give stand-up a try “in response” to Dave Chappelle or Ricky Gervais’ controversial recent specials. I did so because I am both a life-long stand-up comedy fan and a trans woman of color, and yet my current favorite working stand-up comedians are James Acaster, Bo Burnham, and Demetri Martin – all cis, straight white men. This puzzled and frustrated me.

I realized what I appreciate most about each of them — and about some older favorites like Mitch Hedberg and Steven Wright — is their comedy typically focuses on one-liners, wordplay, absurdity, and playing with the form of comedy. They tend to tell jokes rather than stories. It seems as though their cis, straight, white maleness means they aren’t forced to comment on their identities in their work. They’re free to be funny in a way others aren’t.

There are three things in stand-up that I’m tired of. The first I share with most everyone: hackneyed reliance on derogatory tropes, i.e. “punching down.” The other two, however, seem to be the bread and butter of modern stand-up comedy: amusing storytelling from one’s life that leans heavily on having lived through an interesting experience rather than having written a clever punchline, and observations and/or explanations about one’s gender, sexuality, or race.

I am a trans woman of color, and being trans is frequently hilarious. But why should straight white men get to have all the fun writing one-liners and wordplay jokes? Why should they get to be absurd and silly, and observational, rather than relatable? I didn’t want to tell stories about my own life. I’ve done enough of that in my writing on this very website. The saying goes that if you can’t find the art you want to see, you have to create it yourself, right? So I signed up for a comedy class to challenge myself: I wanted to write jokes without relying on identity material.

On the first day of class, this intention was shut down immediately.

The class is for beginners, so our teacher said we were going to start with the basics: mining our lives for material and telling amusing stories. If I took the level two class after finishing this one, they said, I could take my comedy writing to the next level.

That was only the first wake-up call. I’m the kind of narcissist who foolishly, and frequently, tells herself, “This shouldn’t be too hard.” Sometimes I’ve been right! In this case, I was very wrong.

At the second class, we each got a few minutes onstage, in front of each other, to try out some of what we’d written the week prior. I bombed hard. It was like I’d never spoken in public before; I read off my phone, I mumbled, I spent far too long getting to my punchlines, and when I finally did they were weak.

Every comedian shares an experience of bombing as part of their origin story. If you come back the next time and try again, they’ll often say, you might have what it takes. I came home that week dejected but determined to try again.

I could work on my confidence and stage presence, but it’s much more difficult than it seems to know what’s funny. I could practice in front of my girlfriend, but she’s biased in my favor, and comedy just hits different from the stage. I couldn’t get a sense of what worked until I got up in front of my teacher and classmates to see what got laughs.

And I did start to figure it out. I followed our teacher’s instructions and mined my life for material, and some of it was pretty funny. I wrote a story about my childhood, and some personal observations about aging. In doing so I began to understand why so many comedians go there, and why so many audiences love it: there’s power in relatability.

One of the reasons comedy is significant is because laughing at someone else’s tender spots subconsciously allows you to laugh at your own. And it’s still possible to be clever within that framework; just like all art, the form itself is not necessarily hackneyed — artists can choose to have a unique point of view or to tread a well-worn path.

Halfway through class, however, we had to start preparing for the showcase: the week after class ended, we’d each get five minutes on the mic on a real stage with a real audience. I had a decision to make: Would I write about gender? The next few classes were my best opportunity to give it a shot with lower stakes. Instead of telling a trans joke in public at an open mic, I could do a soft launch and see how it felt in front of my class of cis, mostly-white fellow comedy students. So I did.

To keep my options open, I decided to take another risk. I disobeyed our teacher slightly by also writing a few observational one-liners and wordplay jokes that were only loosely related to my actual life: about the dentist, cereal mascots, vampires, microwave popcorn. Each of these was inspired by something that had happened recently, but weren’t actually personal.

That week, I tried out both, and the trans jokes did well — perhaps too well. This is where Dave Chappelle re-enters the conversation.

The Fader quotes a Time interview with Chappelle during which he explains why he quite infamously left Chappelle’s Show at the height of its popularity: “[At a taping], one spectator, a white man, laughed particularly loud and long … [Chappelle] wondered if the new season of his show had gone from sending up stereotypes to merely reinforcing them.”

During my trans jokes, there were laughs in places I didn’t expect or desire them. There was “claughter,” when an audience applauds in agreement with a joke’s politics rather than laughs. And, after class, one of my classmates told me how good she thought they were, and I couldn’t tell whether the comment was smarmy or sincere. Like Chappelle, I couldn’t know whether the jokes were inherently problematic, the audience was wrong, I was being too sensitive, or I wasn’t talented enough to pull them off. So I had to cut them.

However, the one-liners and “joke” jokes also performed well. In fact, they performed better than anything else I’d done all class. “Excellent writing” was our teacher’s feedback for me, which was incredibly affirming. So for the showcase, I mixed some relatable stories with a few clever observations, and — with as much humility I can muster — from my perspective it turned out great for a first effort. You be the judge: The set was recorded and it’s on my YouTube.

Maybe I’ll tell versions of the trans jokes at some point — at a queer comedy night, maybe. Or perhaps I’ll get better and will feel more confident with them, or I’ll write better ones. But struggling with these jokes is complicating the reasons I wanted to try stand-up in the first place.

Taking this class, writing jokes, and actually getting on stage shifted my perspective on comedy significantly. I still don’t want to be pigeonholed as a “trans comedian,” and I don’t want to exclusively perform for other queer people. I just want to be a funny comedian who’s trans. Since the showcase, I’ve gone to a handful of open mics. Some of them were explicitly queer and some weren’t. And as expected, nearly every queer and/or trans comedian had a bit about their identity. Some of them were funny! But many of them felt hackneyed.

My greatest fear in doing comedy is being a hack. If I ever felt like I was going there, I’d give up. However, before I took this class, I thought doing any material about being trans would be hackneyed. But I was wrong. Where I thought comics who are queer, trans, women, or of color were being boxed in by their identities, I was actually the one boxing myself in by avoiding it.

True liberation, of course, is neither being pigeonholed into joking about gender and sexuality all the time, nor being forced to avoid those topics. Observational jokes divorced from one’s identity aren’t a “purer” form of comedy. It’s true that I tend to prefer both writing and listening to them, but I also had a blast writing some clever little takes on true stories from my life.

I can take inspiration from Chappelle’s story without necessarily conforming to his example for how the rest of his career played out. I’m going to follow the laughter, but also focus on being positive and keep my moral compass about me. If I write something truly funny to say about being trans, or come up with amusing and relatable stories from my life, I’ll give them a try. I’m not going to prioritize queer open mics, but I’m not going to shy away from them either.

To my embarrassment, it also became clear I’d overlooked the depth in my favorite comedians’ work. James Acaster’s absurd premises are actually a clever smokescreen for introspective storytelling. Demetri Martin’s graphs and drawings provide piercing insight into his psyche. And, of course, Bo Burnham’s Make Happy was deeply personal underneath its confrontational veneer, and Inside was one of the most revelatory pieces of comedic work I’ve ever seen. I can also take inspiration from them – just not in the way I thought.

Some of the open mics I’ve been to recently have gone well and some have gone poorly. Some things I thought were hilarious have bombed, and some I thought were silly and ill-considered have killed. Comedy is fickle, which is part of what makes it exhilarating. I’ve met and been introduced to a bunch of queer, trans, women, and people of color comedians who are doing hilarious work. I enjoy watching Tig Notaro, Rachel Mac, Patti Harrison, and Angella Dravid, for example, but I’m still searching for comics who scratch that particular “one-liner” itch. (If you’re reading this and want to make some suggestions in the comments, by the way, please do.)

I’ve actually booked a couple of feature slots at comedy shows over the next few months. At this point, I have about 15 minutes of decent material to work with. About half of my best stuff is storytelling and the other half are observational jokes. Trans jokes are not yet part of that archive of material, but they could be eventually — I think I have a decent bit I’m working on about choosing my own name that might be pretty good. The only way I’ll know is by trying them out onstage.

I’m no longer puzzled, frustrated, or worried about this tricky aspect of comedy — now I’m excited. I feel as free as I once imagined the straight, white, cis men comedians felt. I know what I like about my favorite comics, and I’ve expanded my palette for others — and for myself.

If you’re in Portland, OR, come see me onstage sometime and let me know what you think.

Before you go! Autostraddle runs on the reader support of our AF+ Members. If this article meant something to you today — if it informed you or made you smile or feel seen, will you consider joining AF and supporting the people who make this queer media site possible?

Join AF+!