Unidentified, Gladys Bentley,1927-1945. Collection of the National Museum of African American History and Culture.
Gender-Bending Blues: Performer Gladys Bentley began her blues career in the 1920s, singing at rent parties (held to raise rent money by charging attendees) and underground establishments in Harlem, New York. Openly gay, she sang remakes of popular tunes in a deep voice, dressed in her signature men's style of tuxedo and top hat. Drag performers often backed her up at New York's Ubangi Club; she also appeared at the Apollo Theater and the Cotton Club. In his 1945 autobiography, poet and writer Langston Hughes described her as, "An amazing exhibition of musical energy."
Learn more about this trailblazer on the Smithsonian Sidedoor podcast episode "Singing the Gender-Bending Blues."