Bentley, Gladys, 1907-1960

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;

Gladys Alberta Bentley; August 12, 1907, Philadelphia, PA – January 18, 1960, Los Angeles, CA; career skyrocketed when she appeared at Harry Hansberry's Clam House in New York in the 1920s, as a black, lesbian, cross-dressing performer; 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 with women in the audience; Bentley was born in Philadelphia, the daughter of George L. Bentley, an American, and his wife, Mary Mote, a Trinidadian; moved to New York City from Philadelphia at the age of 16; her stage name at the time, Barbara "Bobbie" Minton; began performing at the Ubangi Club on Park Avenue; In 1933, Bentley found herself in the middle of a Supreme Court battle with Harry Hansberry and Nat Palein. Hansberry and Palein sued Bentley to prohibit her from taking her musical to the Broadway division. Hansberry insisted that the club had been built around the popularity of Bentley's success and that he owned a five-year contract over Bentley and her raunchy songs. The duo insisted that Bentley left them high and dry at the rise of the club and wanted to pursue other interests that she could financially benefit from; In 1931, Bentley had a public marriage to a white woman during a civil ceremony in New Jersey whose identity remains unknown. When she relocated to Los Angeles, she married J. T. Gipson, who died in 1952,[15] the same year in which she married Charles Roberts, a cook in Los Angeles; they were married in Santa Barbara, California, went on a honeymoon in Mexico,[15] and had a five-month-long courtship before their divorce. Roberts denied ever marrying her; Bentley died of pneumonia unexpectedly at her home in Los Angeles on January 8, 1960, aged 52.[1] It was initially believed to be the Asian flu but later turned into "pneumonia." At the time of her death, she had been more involved in the church and had just been ordained as a minister despite never getting her official paperwork.