What is known is that off stage, she never fully dropped the persona. She spoke in a lower register, refused to wear skirts in public, and was known to get into bar fights defending the honor of her female co-stars.

Pepi Litman (often spelled Pepi Littmann) was born around in the historic, multicultural port city of Odessa , Ukraine. At the time, Odessa was the louche, vibrant capital of the Russian Jewish underworld and intelligentsia—a bustling Black Sea metropolis of gangsters, poets, and revolutionaries. It was the perfect breeding ground for a rebel.

Pepi Litman died in relative obscurity in (some sources say 1937). Her death certificate, filled out by a clerk who didn’t understand her, likely listed her profession as “actress”—a final misgendering by a bureaucracy that couldn’t see the king for the queen.

Pepi Litman: Born Odessa, Ukraine, circa 1874. Died New York. Defied categories forever.

For a generation of immigrant Jewish women who worked in sweatshops and lived in tenements, seeing Pepi Litman was liberation. On stage, she smoked cigarettes in long holders, slapped cards on tables, and clicked her heels. She represented a freedom from the domestic cage. For male audience members, she was a puzzle they couldn’t solve—a woman who was more masculine than they were, yet undeniably beautiful.

Biographers and Yiddish scholars have long debated Litman’s private identity. Was she a lesbian in a time before that word was public? A transgender man surviving without the language of transition? A businesswoman exploiting the only gimmick that would pay? The record is hazy. She married once, briefly, to a man—a marriage that ended almost immediately. For most of her life, she lived with a series of female “roommates,” which in Yiddish theater circles was an open secret. She was likely a butch lesbian or a trans masculine figure who found her truest expression in the footlights.

Born into a poor, religiously orthodox family, Litman’s birth name was probably Perel, but the rigid confines of the shtetl could not hold her. Legend holds that as a child, she was captivated by the traveling Purim players—the Purimshpil —where men traditionally played female roles. Litman saw the loophole: if a man could be a woman, why couldn’t a woman be a man? By her early teens, she had run away to join a wandering Yiddish theater troupe, cutting her hair, binding her chest, and stepping into trousers for the first time.