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Meet Drag King Pioneer Gladys Bentley

Meet Drag King Pioneer Gladys Bentley

Standing proud in tux and top hat, Gladys Bentley was a trailblazing blues singer and pianist who flouted gender conventions long before Janelle Monáe rocked a three-piece suit. At 16, Bentley ran away from her family home in Philadelphia — where her parents, worried about her masculine tendencies, were subjecting her to hormone treatments — to join the Harlem Renaissance. She scored a gig at Harry Hansberry’s Clam House, a popular 1920s gay speakeasy in New York. By the 1930s, she was headlining at Harlem’s Ubangi Club, backed by a drag queen chorus. Langston Hughes wrote in his 1945 autobiography that she was “an amazing exhibition of musical energy — a large, dark, masculine lady, whose feet pounded the floor while her fingers pounded the keyboard.”

After the repeal of Prohibition, the Depression years were not easy on Bentley, as newly regulated club spaces were frequently targeted and shuttered by authorities for being “disorderly” — code for catering to gays and lesbians. In 1937, she made her way to Hollywood. A 1938 ad that ran in THR touted an “intimate” evening with Bentley “direct from New York” at Frank Irvine’s Mermaid Club at 9015 Sunset Blvd., where The Roxy Theatre now stands. But California’s cross-dressing laws were even harsher. Amid the highly repressive post-World War II era, Bentley, who had been openly lesbian, began wearing dresses, married a man and published an essay in Ebony in 1952 declaring: “I am a woman again.” In 1960, Bentley was studying to become an ordained Christian minister when she died from the flu at age 52.

This story first appeared in the June 19 issue of The Hollywood Reporter magazine. Click here to subscribe.

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