Gladys Bentley (also known by the stage name Barbara “Bobbie” Minton) was a blues pianist, singer, performer, and drag king pioneer. She was born in Philadelphia in 1907. At the age of 16 she moved to New York to pursue a music career during the peak of the Harlem Renaissance. She Rose to fame performing at rent parties, Harry Hansberry’s Clam House, and later Ubangi Club (1934–1937), where she starred with a chorus line of drag queens. She also performed in venues like the Apollo Theater and the Cotton Club, Bentley was one of Harlem’s most visible lesbian entertainers during the Renaissance.
Described by Langston Hughes as “an amazing exhibition of musical energy”, Gladys Bentley dressed up in men’s attire: she was known for her signature tuxedo, top hat and bow tie. She performed bold, bawdy parodies of popular songs of that era in her deep, growling voice and flirted openly with the women in the crowd challenging gender and sexual norms through her performances. Bentley was also one of the highest paid Black women of her time. During her peak she lived in luxury in her apartment in Park Avenue. Gladys Bentley was openly lesbian during the height of her fame and she was known to have multiple female lovers. She was also rumored to be married to a white woman in the 1930s. In 1937 she moved to Los Angeles and then, in 1942 to San Francisco. There, she performed at queer venue’s like Mona;s Club 440. During this period of time she signed with Okeh Records (1929) and recorded blues songs about women wronged by men.
Her popularity declined during the McCarthy Era, when she returned to Los ANgeles and performed at Rose Room until 1952. In 1945 she signed with Excelsior to record heteronormative songs due to political pressure. At that period of time, she began wearing dresses, and married a man (Charles Roberts) in 1952 — a marriage he later denied. She also claimed to be “cured” of homosexuality via hormones and wrote about it in Ebony magazine (“I Am a Woman Again”).
Gladys Bentley died of pneumonia in 1960, at the age of 53.
Gladys Bentley on "You Bet Your Life"
"Portrait of Gladys Bentley (2)." Photograph. 1925. Digital Transgender Archive, https://www.digitaltransgenderarchive.net/files/4f16c3064
"Gladys Bentley: A New Blues Star." Clipping. 1928. Digital Transgender Archive, https://www.digitaltransgenderarchive.net/files/4m90dv69g
"Gladys Bentley and Willie Bryant." Photograph. 1936. Digital Transgender Archive, https://www.digitaltransgenderarchive.net/files/kp78gg56z