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Gladys Bentley: ‘The Brown Bomber of Sophisticated Songs’

Gladys Bentley was born in 1907 in Philly to her Trinidadian immigrant mother and Black American father. She was the youngest of four siblings. She stated, “It seems I was born different. At least, I always thought I was," in an interview with Ebony magazine. She defied gender norms from a young age, often wearing her brother’s clothes and crushing on her female teachers; her family even sent her to doctors to ‘fix’ these behaviors.

At the age of 16, Gladys ran away to Harlem to pursue entertainment in New York City. The 1920’s ushered in the Prohibition Era, and as a result, the rise of speakeasies and gay/queer underground bars. Beginning under the stage name Barbara “Bobbie” Minton, she got her start performing at private parties, but soon made her way to many well-known venues like the Cotton Club and Clam House. Gladys sang the Blues with a deep, loud, growly voice, accompanied by scat singing techniques while her hands quite literally flew across the piano. The songs and lyrics that she sang were shocking to most, with risqué and provocative themes. Her interest in women was no secret when it came to her songs. She was a rowdy entertainer and flirted with her audience, developing allure in her talents and disregard for social norm. Her top hat and tux were exceptionally unprecedented.

Bentley wished to take her performances to Broadway but was blocked by a Supreme Court battle in which the owners of a club she previously worked in decided to sue her for leaving their business. Still, the defiant Gladys went to Broadway in 1933, but was faced with police opposition who locked the doors to places she would have performed. Unfortunately but not surprisingly, Black talent & existence are still blockaded by police today- almost a hundred years later.

The success of Gladys Bentley was not linear. The main attraction at the Ubangi Club from 1934-1937 was Bentley’s musical performances accompanied by a chorus of 8 male dancers dressed in drag. At the height of her heyday, she lived in a Park Ave apartment and claimed that she and her white female partner received a civil union in New jersey. When Prohibition was repealed, Bentley lost popularity with the decline of both speakeasies and tolerance for openly gay people. World War II brought some of that popularity back for her as gay bars expanded along the West coast, where she relocated to Los Angeles to live with her mother. As laws changed, there was a point where Gladys had to carry specific permits to allow her to perform in men’s clothing, for which she was frequently harassed.

In the later years of her career, Gladys had a shift in identity. The 1952 self-written article titled, “I Am A Woman Again” for Ebony magazine outlined Bentley’s reawakening of femininity, and mentioned her being “cured” with medical treatment. Gladys was rumored to have married a man (although he denies they ever married) and she began wearing dresses. She also started studying for ordained ministry, but never completed. This was likely a response to the hostility of McCarthy Era homophobia and anti-communism.

In 1960 at the age of 52, Gladys Bentley died unexpectedly from the flu in L.A.

While Gladys’ fame was highest during the 20’s and 30’s, she will be remembered for her groundbreaking performances and iconic appearances. A large, loud, and proud

Black queer woman, Bentley highlighted the Harlem Renaissance with her talent. Her impact reaches beyond her glory days singing in gay clubs, as she stands as one of the most popular Black entertainers in the country. Gladys reminds us that Black or white, man or woman, queer or not, music is a channel for self expression that connects us all.

Listen to her here.


Reference: Smithsonian Magazine,, and Wikipedia

By Josie Thompson

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