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Gladys Bentley (August 12, 1907 – January 18, 1960) was an American blues singer during the Harlem Renaissance
She moved to New York at the age of 16, and her career as a performer skyrocketed when she appeared at Harry Hansberry’s Clam House on 133rd Street, one of New York City’s most notorious gay speakeasies, in the 1920s, as a black, lesbian, cross-dressing performer.
She headlined in the early thirties at Harlem’s Ubangi Club, where she was backed up by a chorus line of drag queens. She dressed in men’s clothes (including a signature tuxedo and top hat), played piano, and sang her own raunchy lyrics to popular tunes of the day in a deep, growling voice while flirting outrageously with women in the audience.
Bentley was openly lesbian during her early career, but during the McCarthy Era, she started wearing dresses, and married a man at the age of 28 named Charles Roberts. Roberts later denied that they ever married.
She died, aged 52, from pneumonia in 1960.