Odessa in the 1880s was a unique city: a port that blended Russian, Greek, Italian, and Jewish influences. It was here that Litman first saw a traveling Broder Singer troupe. Inspired by the cross-dressing traditions of Purim shpiels (Jewish carnival plays where men played women and vice versa), she realized that a woman in trousers could command more power, more laughs, and more pathos than a woman in a corset. Pepi Litman was not a drag king in the modern sense. She was a prima donna of parody . Her signature act involved a lightning-fast transformation: one moment she was a sobbing mother, the next she would slap on a bowler hat, puff a cigarette, and swagger across the stage as a slick, cynical "dandy" or a naive yeshiva boy.
On Second Avenue, she competed with giants like and Molly Picon . But Litman had a niche no one else could touch. She specialized in the badkhn-shtick (comedic jester work) but with a sapphic subtext that flew right over the heads of the conservative Yiddish press.
It is unclear if Litman identified as what we would call "transgender" today or as a "gender-nonconforming performer." Most evidence suggests she lived her private life as a woman (she married a violinist named briefly in 1903), but off-stage, she was often photographed in tailored suits, smoking cigars with a smirk. Decline and Disappearance The advent of talking pictures and the decline of Yiddish theater after the 1929 stock market crash hit Litman hard. Her humor—linguistic, intimate, and steeped in immigrant irony—did not translate to Hollywood musicals. The last known sighting of Pepi Litman is a tattered playbill from Buenos Aires, Argentina in 1935, where she performed for a dwindling community of aging Yiddishists.
Her most famous role was (a parody of Alexander II’s telegraph clerks). She would stride on stage in a too-tight military jacket, tangled in telephone wires, singing: "I am a modern man, a telephone man, But my mama still calls me by my girl’s name!" The "Grand Tour" of Exile Due to the pogroms of 1905 and rising antisemitism in the Pale of Settlement, Litman joined the great Jewish migration westward. She became a star of the Romanian Yiddish theaters (Bucharest and Iași) before sailing to London and finally landing at the epicenter of Yiddish culture: New York City’s Second Avenue .