Bentley, Gladys, 1907-1960

Gladys Alberta Bentley (August 12, 1907 – January 18, 1960)[1] was an American blues singer, pianist, and entertainer during the Harlem Renaissance.

Her career skyrocketed when she appeared at Harry Hansberry's Clam House in New York in the 1920s, as a black, lesbian, cross-dressing performer. She headlined in the early 1930s 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 tail coat and top hat), played piano, and sang her own raunchy lyrics to popular tunes of the day in a deep, growling voice while flirting 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 tried to continue her musical career but did not achieve as much success as she had had in the past. Bentley was openly lesbian early in her career, but during the McCarthy Era she started wearing dresses and married, claiming to have been cured by taking female hormones...

In her top hat and tuxedo, Bentley belted gender-bending original blues numbers and lewd parodies of popular songs, eventually becoming Harlem royalty. When not accompanying herself with a dazzling piano, the mightily built singer often swept through the audience, flirting with women in the crowd and soliciting dirty lyrics from them as she sang; By the early 1930s, Bentley was Harlem’s most famous lesbian figure — a significant distinction, given that gay, lesbian and gender-defying writers and performers were flourishing during the Harlem Renaissance. For a time, she was among the best-known black entertainers in the United States; But Bentley was the first prominent performer of her era to embrace a trans identity, implicating her body differently in these acts of musical defiance. (Throughout her life, Bentley used female pronouns to describe herself — at least in public.); Gladys Bentley was born on Aug. 12, 1907, to Mary Bentley, who was from Trinidad, and George Bentley, an American, and she was raised in Philadelphia; In 1923, at 16, she left home for New York City, where the Harlem Renaissance was already in high gear; But it was at the Clam House — Harlem’s most popular gay-friendly speakeasy, on 133rd Street, nicknamed Swing Street for its countless underground clubs — that Bentley established herself as the main attraction; In 1937, Bentley left New York for Los Angeles. She became a leading entertainer there and in the Bay Area, though she sometimes had to wear skirts onstage to appease club owners; By 1958, she said she had completed an autobiography, “If This Be Sin,” but it was never published. Bentley died in 1960, from complications of the flu, at 52, while studying to become a Christian minister;