Before the rise of radio and movies, vaudeville was the most popular form of mass entertainment in the United States. From the late 19th century to the 1920s, networks of theaters in different cities would book a variety of acts that toured together as a show. The skits included singers, dancers, magicians, and comedians. But a vaudeville show was considered incomplete without one or two female impersonators, the most successful of whom were gay men.

Probably the greatest female impersonator of the vaudeville era was Julian Eltinge (1883-1941), born William Julian Dalton near Boston. He first entertained in drag at age 10, when he appeared in a local musical revue. Eltinge went on the vaudeville circuit in 1906, wowing audiences with a sketch called “The Sampson Girl”—based on the Gibson Girl, a willowy, ultrafeminine vision of American womanhood made popular by magazine illustrator Charles Dana Gibson. Eltinge was known for his choice of tasteful, fashionable attire and for including in his repertoire ideal types like “The Bathing Beauty,” “The Bride,” and “The Little Girl.” He also occasionally portrayed historical figures like Salome.

By 1912, Eltinge was the highest paid act in vaudeville, earning $1,600 a week; that same year, a Broadway producer named a theater on New York’s 42nd Street in his honor (it’s now part of a multiplex called the Empire). Critics and audiences alike were mesmerized by his ability to walk, speak, and sing so convincingly like a woman. While other female impersonators simply parodied women, Eltinge attempted to transform himself. In a 1909 interview, he disclosed that it took him two hours to “become” a woman. “It depends on where you put the paint,” he explained, “not how much you splash on.” Before each performance, Eltinge’s Japanese male dresser corseted his normally 38-inch waist to a svelte 24 inches.

The RuPaul of his day, Eltinge endorsed women’s cosmetics and corsets and even had his own brand of cold cream. His vaudeville fame also brought him roles in the legitimate theater and in 15 Hollywood movies. One of these films, An Adventuress (1916; later reissued as The Isle of Love), starred Rudolph Valentino, who was rumored to have been Eltinge’s offscreen lover. After the Italian star’s untimely death in 1926, rumors circulated in the drag world that Eltinge was the mysterious veiled Lady in Black who brought roses every year to Valentino’s grave.

Eltinge, however, always denied insinuations about his sexuality. “I just like pearls,” he explained of his cross-dressing penchant. To compensate for gossip—which was fueled by the fact that he lived with his mother and never married—Eltinge purposely butched it up offstage. He was known for getting into fistfights, beating up stagehands and fellow vaudevillians who dared to question his masculinity.

With the end of the vaudeville era, Eltinge’s career and fortune slipped into decline. Before his death from a cerebral hemorrhage in 1941, he suffered from numerous health problems related to his career, including kidney ailments caused by years of being cinched into tight corsets.

Second only to Eltinge in the vaudeville world was Bert Savoy (1888-1923), who was born Everett McKenzie in Boston. Savoy got his start singing in a chorus, then launched his solo drag career in the saloons of the West. In the 1910s, he came back east and teamed up professionally and privately with handsome Jay Brennan (1882-1961), who had once been a female impersonator, too, but now took the role of Savoy’s “straight” man.

Unlike the prim, proper “Sampson Girl,” Savoy’s drag persona—although as elegantly attired as Eltinge’s—was an over-the-top character who flirted outrageously, shook her hips, and dished the dirt. Drag lore has it that Mae West borrowed Savoy’s walk and adapted one of his coquettish lines—”You must come over!”—to her signature “Come over and see me some time.” Savoy credited much of his success to his ability to listen to and learn from his female fans. “They write or telephone me with little feminine things,” he once said, explaining that he often turned the women’s ideas into naughty gags for his act.

Probably because he was as effeminate offstage as on—he camped it up and always referred to men as “she”—Savoy entered briefly into a marriage of convenience to hide his homosexuality. The marriage ended in 1922, however, when the woman emptied out their bank account and left town.