Next to Transitioning, Standup Comedy Is a Piece of Cake

Riley Silverman is a white, trans, lesbian version of Kumail Nanjiani—or so she hopes. The Los Angeles-based comedian's other aspiration, she told me, is "playing the person who annoys Larry David" in an ensemble cast. But as she looks ahead to her forthcoming role in the second season of Cameron Esposito and Rhea Butcher's acclaimed webseries Take My Wife, Silverman has more metaphysical goals, too: "My hope is that trans girls who look like me see me on this show and feel a little more okay with themselves."

But don't let that make you think she's self-important. "Don't worry," she's quick to add. "I bombed an audition for a movie like a week after I wrapped [Take My Wife]. I know I'm still just an out of work actor in LA."

Well, not quite. After nearly fifteen years in standup and a starry-eyed move from rural Ohio to LA, Silverman's acerbic wit has caught plenty of attention: her appearance on Comedy Central's short-lived Not Safe with Nikki Glaser certainly opened doors, but not before the release of her debut album Intimate Apparel, which helped her become head writer on Maximum Fun's comedy quiz podcast International Waters. Last month, hot on the heels of Intimate Apparel's re-release under the label ASpecialThing, she headlined Portland's first annual Queer Comedy Festival alongside Guy Branum and a host of other LGBTQ comedy stalwarts.

But what makes Silverman's rise to prominence notable is that she did it all while transitioning on stage and in public, allowing audiences a rare glimpse of a trans woman at her most vulnerable.

Silverman compares her path to womanhood to a Family Circus-style dotted line, "basically touching and interacting with everything in the neighborhood rather than complete the simple task." Although she first came out as trans while living in Ohio, years before her comedy career took root, "I never fully committed to an en femme persona before I started transitioning," she said. "I'd occasionally try on femme names, and of course I bought the odd wig or two, but a lot of the things that crossdressers or pre-transition trans women often do to mitigate dysphoria"—wearing padded bras, for instance—"actually only increased mine, which drove me back into the closet."

After starting her career while presenting as male, scraps of Silverman's true identity slowly became apparent. She began wearing skirts and dresses more frequently, and initially identified as a crossdresser, something she had to address with audiences before moving on in her sets. That became its own challenge, as she was forced to determine her wardrobe based on the amount of stage time she was allotted on a given night. "As time went on, I started testing the waters to see how little I could say about it before moving into my material on other topics."

For a while, Silverman accidentally led a double life. Someone, once told her they thought she was two different people: "a cross-dresser and a more average guy, and that one of us was stealing the other's material." She made a few terrified attempts to come out onstage, but found herself so frightened to do so that she'd end up just stammering through her sets. Finally, though, Silverman was able to steel herself with "fake confidence," and said everything that was on her mind, and killed.

It might have been a mere façade of bravado that night, but the onstage confidence Silverman's been able to find since then has fueled her brand of gentle-yet-sassy comedy and propelled her ever upward. It's created a feedback loop of good vibes: "The more confident I feel as myself the better I get onstage, and the more I improve as a comic, the more confident and excited I get about life," as she put it. Introducing herself on Intimate Apparel, Silverman smirkingly strong-arms the audience into accepting her gender identity. "I've found the comedy show goes a lot better if you guys are just cool with it," she remarks breezily, "so we're gonna do that. That sounds like fun."

"By the way," she adds, "society would go a lot better if you guys were just cool with it. So let's do that too."

Watch "Standup Comedy… On Acid":

"I think to some degree you have to be a little fearless when you're doing comedy or else you get in your head and second-guess everything," she said. Experience has taught her that she can get away with behavior onstage that her friends would call bitchy in everyday life, so she's unafraid to provoke her audiences, cisgender or otherwise—and anyway, Silverman trusts her fans. "I'm kind of making the assumption that the audience will take [that joke] as a 'Haha, you're right, we are terrible' kind of moment," she said. "I feel like, you know, I'm white, so I've been called on my privilege in similar ways by comics of color, and I can take it, so I assume my crowds can too."

In a way, Silverman is more nervous about the lingering effects of her past than any bad reactions she may get from what she says in the future. Among her YouTube clips are several bits from 2013, when she still called herself a crossdresser; she said looking back on that time can be awkward and uncomfortable. "Sometimes I fear that language I used to use at a time where I was still unpeeling my identity will eventually be used against me, or to invalidate the person I am now," she said. It's something Silverman has experienced before; early in transition, the trans community on Tumblr would circulate Silverman's posts and accuse her of being cisgender "because I didn't look how they thought I should or didn't use the right language… or because I was still figuring my shit out."

But again, Silverman's career has been defined by her ability to embrace being vulnerable. Intimate Apparel was intentionally recorded two days before Silverman began the nerve-wracking process of hormone replacement therapy, and ends with an affecting (yet raunchy) bit about the death of her brother. And as much as it might bother her to look back on her former self, Silverman said she won't take down her old material. "Leaving that journey stuff up there as a note to say 'Hey, it's okay if you don't know where you're going yet,' feels important to me," she explained. "If it helps one young scared trans kid feel less like I did when I was their age, it's worth [a] bit of discomfort."

At a time when trans activists are maligned by the right as joyless social justice warriors, Silverman single-handedly slays that stereotype, baring her soul with wit and candor. That's what makes her such a great match for Esposito and Butcher ("Cam and Rhea just really give a shit, you know?"). But with her wry observational comedy, radical openness, and casually inviting demeanor, Silverman may be nothing less than the comedian America needs right now.

Follow Sam Riedel on Twitter.