Unlike her contemporary, the British male impersonator Vesta Tilley (who played polished, patriotic gentlemen), Pepi’s men were Jewish Everymen: the schlemiel , the luftmensch , the overworked tailor dreaming of being a cowboy. She gave voice to the masculine anxieties of a community caught between Old World patriarchy and New World possibility. Biographical details on Pepi Litman are frustratingly ephemeral—a testament to the way history has treated queer performers, immigrant artists, and women who refused to be ladies. We know she was married, briefly, to a fellow performer—a union that ended quietly. Rumors followed her: that she lived openly with a female companion in a tenement on East Broadway; that she was arrested once for wearing “men’s attire” in a public thoroughfare (a common charge against gender-nonconforming women of the era); that she was beloved by the Yiddish literary crowd, including the young Isaac Bashevis Singer, who was said to have modeled a minor character after her swagger.

They were known as Pepi Litman. And long before Marlene Dietrich donned a top hat, long before the term “drag king” entered the vernacular, this immigrant from the shtetls of Ukraine was blurring every line on the map of gender and performance. The exact date is lost to the chaos of empire, but scholars place the birth of the performer known as Pepi Litman around the early 1880s in the Pale of Settlement, specifically in the region of Volhynia, Ukraine—then part the Russian Empire. To be Jewish and talented in the shtetl was to be born with a target on your back and a song in your heart. The pogroms of the 1880s sent waves of refugees westward, and young Pepi—born either into a family of modest klezmer musicians or small-town merchants, depending on the fragmented record—was among them.

Her signature was a form of theatrical androgyny that confused as much as it delighted. She would sing love songs to women, using the masculine grammatical forms in Yiddish, but with a knowing wink that acknowledged the artifice. For Jewish immigrant audiences—many of whom had left behind rigid gender roles in the shtetl for the bewildering freedoms of the New World—Pepi was a revelation. She was the anxiety and the ecstasy of assimilation made flesh.

Her most famous number, rarely recorded but often described, was a parody of the operatic tenor. She would stride out in a frock coat too large for her, a fake mustache that seemed to have a life of its own, and proceed to butcher a Puccini aria with deliberate, hilarious off-key notes—before ripping off the mustache mid-crescendo and finishing the song in a pure, beautiful soprano. The audience would erupt. It was drag, deconstruction, and virtuosity in a three-minute package.

She took her final bow long ago. But somewhere, in a dusty archive, a sepia photograph survives: Pepi in a three-piece suit, one hand in her pocket, one eyebrow raised. She is smiling. And she is waiting for you to catch the joke.

In the smoky, glittering underworld of early 20th-century vaudeville and Yiddish theatre, where heartache was sold with a fiddle tune and comedy was a survival tactic, one figure stood out not just for their talent, but for their audacity. They stepped onto the stage in a sharp-waisted coat, a tilted fedora, and a swagger that suggested they owned the sidewalk. Then they opened their mouth, and a contralto voice—rich, wry, and weathered—rolled out like a challenge.

By Anya Shapiro

Unlike many of her contemporaries who fled to New York’s Lower East Side, Pepi’s early career trajectory wound through the cabarets of Bucharest, the beer halls of Vienna, and the music halls of London. It was in these liminal spaces—neither opera nor burlesque, but something grittier—that she honed her act. To call Pepi Litman a “male impersonator” is both accurate and insufficient. In the Yiddish theatre tradition, male impersonation had a specific, often sentimental niche. Usually, a female performer would don a costume to play a young boy—a yoshke —for comic relief or a single song. But Pepi did something different. She performed as a man , not a caricature of one. She was the rakish leading man, the street-smart dandy, the rogue with a golden voice.

Birthplace Ukraine — Pepi Litman Male Impersonator

By Anya Shapiro