Bentley was open about being a lesbian and used her gender bending act to great advantage during the "anything goes" 1920's. Born in Pennsylvania, she left home at 16 to make her way to New York to be part of the Harlem Renaissance and to find a more tolerant community to thrive in. In her words, "It seems I was born different. At least, I always thought so...From the time I can remember anything, even as I was toddling, I never wanted a man to touch me...Soon I began to feel more comfortable in boys clothes than in dresses."
She got her start singing at rent parties and buffet flats, moving on to speakeasies and night clubs eventually headlining at the Clam House (one of New York's most notorious gay speakeasies) and the Ubangi Club. She wowed audiences in her signature top hat and spotless white tuxedo, using her powerful voice to belt out raunchy parodies of popular blues songs and show tunes in front of a chorus line of drag queens. She was openly flirtatious with the women in the audience and made the gossip columns often, even claiming to have married a white woman in Atlantic City, N.J.
During the Depression, many of the clubs of "Jungle Alley" in Harlem closed and the social climate was less tolerant of personalities outside what was considered the social norm. Bentley moved with her mother to Los Angeles in 1937 and was able to continue performing successfully, especially during World War 2 in the bars on the West Coast that catered to gays and lesbians in the service. She was a popular performer among lesbians at Joquin's El Rancho in Los Angeles and Mona's 440 Club in San Francisco despite her frequent run-in's with the law for wearing men's clothing. She also made many successful recordings but they were incredibly tame compared to her live act and never used her lesbian lyrics.
By the 50's, the pall of McCarthyism in U.S. politics made being openly gay a dangerous proposition. For Bentley, who had been one of the most open performers about her sexuality, it was a serious issue. With an aging mother to support and fear for her own survival, she started wearing dresses and toning down her act. She claimed to have married newspaper columnist J.T. Gibson (who denied they had wed) and in 1952 she did marry a man 16 years her junior who she would later divorce. She also wrote a desperate article for Ebony magazine claiming to have been cured of her homosexuality by taking female hormones. Through it all, she continued to perform until her death from a flu epidemic in 1960 at the age of 52.
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