Transgender comedian Ian Harvie thinks Donald Trump would really like him.

“I am a trans man—I am a man with a vag,” he explains during his Seeso special May the Best Cock Win. “And Trump is a man who hates women but he loves pussy so I’m thinking I’m the perfect guy for him.”

It’s one of many bracingly honest, totally irreverent, and strangely educational bits in Harvie’s provocatively-titled special—believed to be the first hour-long standup special ever to feature an out transgender comedian.

The 48-year-old comic from Maine—who will be touring California, Texas, and Maine starting next month—has had a long road to this point. In 2006, after moving to Los Angeles, Harvie happened to meet comedian and all-around phenomenon Margaret Cho at a comedy room.

A chat after Cho’s practice set turned into an exchange of phone numbers followed by three years of Harvie being her opening act on the road—a period that Harvie refers to now as the “biggest, quickest comedy lesson” he’s ever received.

“I’m so grateful for her elevating my voice and for her actually seeing that trans people need representation even in standup comedy,” he tells me in a phone interview.

Harvie has had the material for May the Best Cock Win for years. It’s a mixture of confessional and observational comedy about gender and identity, ranging from stories about his chest masculinization surgery—in which his pancake-sized “IHOP nipples,” he jokes, were replaced with “button nipples”—to his ardent belief that everyone can relate a little bit to being transgender.

“If you feel 100 percent okay about your body in direct relationship to your gender,” he announces near the end of the set, “then you’re the fucking weirdo.”

But getting the green light for an hour-long special was difficult because production companies, he explains, generally “want you to have some sort of TV credit.” And in a world where transgender actors are still having a hard time getting cast even in transgender roles, those crucial credits can be especially hard to stack up.

It’s a barrier to entry that can be easier for cisgender comics to overcome. But in 2014, Harvie landed a role as a transgender teaching assistant on the Amazon series Transparent, followed by 2016 guest turns on the ABC series Mistresses and the ABC Family series Young & Hungry.

“To get all those stars aligned—it’s hard,” he tells me. “[But] I’m not resentful at all.”

Instead, he attributes his current precedent-setting success to transgender performers like Alexandra Billings, Laverne Cox, Candis Cayne, and others who carved out room for trans representation on TV.

But it’s also success that Harvie richly deserves. May the Best Cock Win has the unique quality of being old and new at once, a traditional kind of stand-up comedy delivered by a radically different kind of voice. It turns out that “men think like this, women think like that” observations can actually feel fresh when you hear them from someone who has experience being perceived as both of those genders.

Harvie, for example, remembers what it was like to not have as much testosterone in his body as he does now, telling his audience that he’s become a “horndog now in ways that I never used to be,” to the point that he’d sleep with an egg salad sandwich if it were tasty enough.

“It’s more acceptable, it’s more familiar,” Harvie says of the choice to do this kind of comedy. “The style is very familiar to people listening or watching, so it’s not hard for them to wrap their head around it.”

The material emerged organically from Harvie’s own experience transitioning from female to male, which hasn’t always been funny. But like so many performers belonging to marginalized groups, he learned how to use humor as a coping mechanism.

“If I couldn’t laugh, I’d die,” he tells me. “And I think a lot of trans people probably feel that way.”

He is keenly aware that the struggles transgender people face aren’t always funny—and he devotes a few minutes of his comedy special ensuring that his audience is aware of how transgender women are treated—but he believes that laughter can be “healing” even in the darkest times.

“In order to have that sort of daily reprieve to continue on to the next day, we have to be able to laugh about this shit,” he says.

The familiar, relatable quality of May the Best Cock Win ultimately makes it into an oddly effective primer on transgender male identity. Many of the invasive questions that curious cisgender people might want to ask a transgender man—about sex, genitalia, and getting through airport security—aren’t just answered, they’re answered to hilarious effect.

For instance, in the show’s titular joke, Harvie explains that not having a penis attached to his body actually gives him at least one advantage in the dating world.

“If you go out with me, we’ll get you what you want,” he says of trips to adult stores at the start of new relationships. “May the best cock win.”

Harvie tells me that the educational side effect of the special is a “secret goal” of his, although not the primary one. In his experiences touring the country, he’s found that comedy is a surprisingly powerful way to build empathy for transgender people.

“You’re not at a podium giving a speech,” he says. “You’re not wagging your finger at people telling them what to think. You’re giving them new information, making them laugh, which is actually a very intimate thing to do with each other. People think that laughter is not intimate, but what it actually does is it opens you up to receive new information.”

The net effect, he’s observed, is that audiences might not fully internalize all of his material in the moment but “they do go home and they inevitably have a frame of reference for who some trans people are.”

By being so open about his own personal experiences of being transgender, Harvie explains to me, he is “really annoyingly making people love [him] so they can’t hate [him].”

“You can’t hate someone once you know their story,” he says.

Ian Harvie’s standup special May the Best Cock Win is available on Seeso and now on digital audio. His upcoming tour dates begin on April 8.