Gladys Alberta Bentley (August 12, 1907 – January 18,1960) was a popular blues singer, pianist, and entertainer during the Harlem Renaissance.

Gladys’ career took off when they performed at Harry Hansberry's Clam House, a famous gay speakeasy in New York in the 1920s. Bentley was a black, queer performer who often wore men's clothing. Historians have often described Gladys as a lesbian but there is plenty of evidence to suggest Gladys identified as a trans man.

In the early 1930s, Gladys became the star of Harlem's Ubangi Club, performing with a group of drag queens. Gladys was known for their distinctive style, wearing a tail coat and top hat, playing the piano, and singing her own playful, sometimes risqué lyrics in a deep voice. They were also known to flirt with women in the audience during their shows. Gladys was arrested many times during their career for ‘dressing as a man’. It is alleged Gladys would often be released from jail the following morning in their top hat and suit and head straight back to the club to perform.