For Rachel Kaly, growing up in New York City had its ups and downs. At 16, the comedian, who uses she/they pronouns, went to a warehouse party with a friend. “It was so scary,” Kaly tells me. “I danced with this one guy who wasn’t holding me tight enough, and he thrust into me, and I flew across the dance room.” Long story short, the high-schoolers ended up sleeping on newspapers on the roof of another friend’s building. Kaly finished the journey alone, dozing off on a High Line bench until a family friend woke her up.

Anecdotes like this one are typical of Kaly, who speaks in a slow, deadpan voice. The comedian, who is now 28 and lives between Los Angeles and New York City, returns to the same themes: being Jewish, gay, mentally ill, and growing up in New York City with an absent father. Kaly’s jokes border on depressing, but her sharpness and lack of inhibition keep them hilarious. She’ll perform them twice in New York this month—on February 16, at Union Hall, and three days later at the Bell House with Robby Hoffman, the co-host of her comedy podcast, Too Far.

When Rachel Kaly was growing up, her dad “always had Seinfeld on—like, all the time.”

Kaly often posts comedy videos on the YouTube channel she started in 2015, when she was 20. “I Sued 9/11 for Making Me Gay,” a five-minute video posted last March, shows Kaly walking around Ground Zero. “Being from New York and of the Jewish persuasion, I’m pretty litigious,” she says. “So I decided to sue 9/11 for making me gay, to get my revenge.” As a child, Kaly watched from a window at school as the Twin Towers fell. This triggered many of her neuroses and mental illnesses—O.C.D., panic disorder, and a personality disorder.

When Kaly was growing up, her dad “always had Seinfeld on—like, all the time.” At age nine, she joined a youth program at Gotham Comedy Club, a troupe where members write and perform their own material. Although Kaly had done that all her life, she “felt very isolated and not funny” as the only girl in the group. In high school, she focused on playwriting and theater direction.

“I didn’t actually find my voice and make myself laugh until college,” says Kaly. As an undergraduate at Wesleyan University, she did improv and sketch comedy, and frequently made trips back to New York to perform comedy shows. She spent her college summers at Upright Citizens Brigade, Second City, and the Annoyance Theatre.

I first watched Kaly perform in Hospital Hour, the monthly show she staged last year at Union Hall. (In August, she’s bringing it to the Edinburgh Festival Fringe.) For an hour, Kaly recounted all the times she’s been hospitalized due to mental illness. She gave her detailed opinions about an intensive group-therapy program. Throughout the performance, she showed the audience several narcissistic and curt e-mails she’s received from her father.

A still from a trailer for Kaly’s show Hospital Hour.

While Kaly spoke casually, and her stories were a stream of consciousness, she carefully constructs and workshops her act. After completely improvising her first two shows in January 2023, Kaly began recording her sets, re-watching them, then re-writing parts. Even if she feels confident in her act, she continues to watch the recordings and make slight changes.

Kaly spends much of her time in Los Angeles. “I’m in a very career-oriented time in my life,” she says. “That is the priority.” In L.A., she writes for Andy Samberg and Neil Campbell’s animated series, Digman!, and does the voice for a character named Trisket.

With all this success, Kaly wonders how people perceive her. “With any question I’m asked, I pray to God that I come across as something that people understand,” she says. What she does know is her ultimate goal: “I’ll do everything, and I want to do everything.” In the meantime, Kaly will focus on learning how to drive. Living in Los Angeles is hard without a license. “It’s not working. I can tell you that.”

Rachel Kaly will perform Major LOL Vibes at Union Hall, in Brooklyn, on February 16, and Too Far Podcast: Live at the Bell House, in Brooklyn, on February 19

Jeanne Malle is an Associate Editor at AIR MAIL