The day that Louisa Jacobson and I are scheduled to chat over Zoom is a big one, for both New York and Jacobson herself. We’re meeting on the second day of a record-breaking heat wave, the culminating week of Pride Month, and, as it happens, the one-year anniversary of Jacobson publicly coming out. The third season of HBO’s The Gilded Age—in which Jacobson plays Marian Brook, a doe-eyed newcomer to late-1800s Manhattan high society—premiered a few days prior. And the night before, Zohran Mamdani clinched a historic victory over former governor Andrew Cuomo in New York City’s mayoral primary.

“I ranked Zohran as number one,” says Jacobson. “So, yay. I’m really excited. It’s a very cool breakthrough moment in New York politics.”

Mamdani’s win also coincided with the American premiere of Trophy Boys—a play written by Emmanuelle Mattana and directed by Danya Taymor—off-Broadway at MCC Theatre. In it, Jacobson and the rest of the assigned-female-at-birth cast don drag to play an all-boys senior debate team as they prepare to face their sister school in the final battle of their high school careers. The task? Arguing the affirmative for the prompt that “feminism has failed women.”

“The opportunity during Pride Month to be doing drag and a show like this is so cool,” says Jacobson, “and to investigate gender as performance and dive deep into exploring the more masculine parts of myself.” She also notes that this kind of drag is the reverse of what is usually represented in popular culture. “We don’t see it as often as we see queens, you know? It’s less digestible. People don’t always understand how to receive it. So we were batting up a little bit with that, but it’s been really fun.”

Even as it navigates themes of privilege, toxic masculinity, and the nuances of sexual-assault allegations, the play still manages to feel boisterous and campy. It even has one horny dance break, in which all the boys gyrate to Pretty Ricky’s 2005 hit “Grind With Me”—making literal the already effectively masturbatory nature of their debate. As the quartet humps chairs, doms desks, and spanks the air, it’s clear their intellectualizing is merely a coping mechanism for that specific, liminal teen space of extreme lust exacerbated by a maddening lack of experience.