Carolines on Broadway isn't really known as a space for the avant-garde, but once a month the club turns into the surrealist playground of Peter Smith, a nonbinary cabaret upstart whose batshit-crazy variety show features burlesque, lip syncs, and meandering storytelling.

“Anyone who wants to come is invited and welcome,” Smith says. “There are straight people, gay people, trans people. There are all shapes and sizes." While the crowd usually ends up having a good time, Smith says, "They’re probably like, 'How is this going to end? I need to see how this carousel finishes.'”

Smith is part of a growing and interconnected community of trans and nonbinary comedians entering the mainstream. They have aspirations like most others—to play the big room, to score a sitcom or a book deal—but they also have to navigate their audience's (and the industry's) limited understanding of who they are. As America begins its conversation about gender identity, trans comedians must serve as educators, ambassadors, and defenders—all while somehow keeping it funny.

Trans comic Patti Harrison has emerged as a powerhouse in Brooklyn’s comedy scene: In July, she appeared on The Tonight Show with Jimmy Fallon to address Donald Trump’s ban on transgender service members in the U.S. military.

“Donald, you are so stupid," she deadpanned. "You’re lucky you’re so hot.”

“My comedy is very dumb, and dirty, and stupid," Harrison says, "and the attention I was getting was for an explicitly political set.” She was thrilled the Tonight Show producers invited a trans comic onstage, but was taken aback by the deluge of response.

“People are like, ‘You’re an activist and an advocate, what is that like?’ That is not my platform," she explains. "I definitely am socially conscious because I have to be—I don’t have the privilege of making non-political work—but this is the first time I’ve had to answer a lot of questions about what the community thinks about this or that. I don’t know! I’m one person. Not all trans people are in touch with each other.”

In addition to the pressure to act as spokespeople for their community, trans comedians are also expected to either play into or subvert stereotypes. “At some time or another, you have to lean into your oppression,” Harrison says, “because that’s what people want to see from you.”

But in a community defined by self-determination, many performers strain at embodying anything but themselves. Standup comedian Jes Tom says if they don't explain their identity as a queer, nonbinary Asian-American, the audience will start drawing its own conclusions.

“A lot of the standard set that I do for straight audiences is about they/them pronouns, and being a fifth-generation American—stuff like that, because people misread you a lot of the time," explains Tom (above). "They don’t know what it is they’re looking at, and they’re going to make assumptions about you. One of my jobs as a queer trans stand-up is to explain myself so that the audience starts reading me the way that I am.”

Some stereotypes are faced head on: Smith has performed as Caitlyn Jenner in live shows including Katdashians: The Musical. “Someone has to fucking do it," they explained. "It falls upon me to drag that lady through the pitch. But not to villainize her—even though she’s a villain—which is tricky because I’m making fun of the people I represent."

Tan, a mono-monikered actress and stand-up comic, pushes the envelope even further by incorporating cultural curiosities about trans people's anatomy into her material.

“I talk about my penis a lot," Tan says. "There’s this cliche that male comedians go onstage and talk about their dicks, so I was like, 'As long as I still have my penis, I’m going to joke about it." It's also a way for her to disarm people who don't take her transition seriously or think it's a phase. "When I say I love my small penis, everyone believes that I’m a woman.”

Unbound by expectations of playing into gender roles, some acts can fully unleash. Lena Einbinder is a nonbinary performer known for ghoulish characters and daring stage gambits. They're aware of audience misconceptions and embraces the mystery.

“A lot of my characters are nonbinary or their gender is never revealed,” Einbinder says. “It’s ambiguous, so people are questioning why they would try and gender the character.”

But sometimes the conversation is taken out of non-cis comedians' hands. “A lot of the time, if I go to open-mic nights, I become someone else’s joke,” says Tan. “I do a set and I have to get out of there. I know if I stay, it becomes, 'Oh my god, there’s a trans person on stage!' And everyone after me has to make a joke about it. I know a lot of them don’t mean anything. But I know I’m kind of a standout. About two-thirds of the time someone has to say something afterwards.”

But as queer and inclusive shows become more common, the behavior is changing: Harrison recalls an improv show at Ohio State when she first came out as trans.

“There was a group from New York, all guys, and they did this set that was hyper-transphobic about a trans woman who kept getting surgery and kept transitioning back and forth. I was sitting in this auditorium mortified, and everyone was dying laughing. I was silently, like, 'Oh, this is what I’m in for.’ But I’ve seen those same guys perform since, and they don’t do that shit anymore."

"People are seeing that the next wave of comedy is more conscious of punching down," she adds, "that being misogynistic or racist or transphobic or Islamophobic onstage won’t fly anymore.”