Gladys Bentley (August 12, 1907 – January 18, 1960) was an American blues singer during the Harlem Renaissance.
Bentley was born in Philadelphia, Pennsylvania, the daughter of American George L. Bentley and his wife, a Trinidadian, Mary Mote. She appeared at Harry Hansberry's "Clam House" on 133rd Street, one of New York City's most notorious gay speakeasies, in the 1920s, and 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.
On the decline of the Harlem speakeasies with the repeal of Prohibition, she relocated to southern California, where she was billed as "America's Greatest Sepia Piano Player", and the "Brown Bomber of Sophisticated Songs". She was frequently harassed for wearing men's clothing. She claimed that she had married a white woman in Atlantic City.
Bentley was openly lesbian during her early career, but during the McCarthy Era, she started wearing dresses, married a man (who later denied that they ever married), and studied to be a minister, claiming to have been "cured" by taking female hormones. She died, aged 52, from pneumonia in 1960.
Fictional characters based on Bentley appeared in Carl Van Vechten's Parties, Clement Woods's Deep River, and Blair Niles's Strange Brother. She recorded for the OKeh, Victor, Excelsior, and Flame labels.
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