Gladys Bentley (1907-1960) was a blues pianist, singer, performer, and drag king pioneer.
Born in Philadelphia, she moved to New York City at the age of 16 and began her career as a performer at Harry Hansberry's Clam House on 133rd Street, one of the city's most notorious gay speakeasies. In the early 1930s, she headlined at Harlem's Ubangi Club, where she was backed up by a chorus line of drag queens. She dressed in men's clothes (including a signature tuxedo and top hat), played piano, and sang her own raunchy lyrics to popular tunes of the day in a deep, growling voice while flirting with women in the audience. Bentley was openly lesbian early in her career, but during the McCarthy Era in the 1950s, she started wearing dresses and married (within five months of meeting) Charles Roberts, age 28, a cook, in a civil ceremony in Santa Barbara, California, in 1952. Roberts later denied that they had ever married. Bentley also studied to be a minister, claiming to have been "cured" by taking female hormones. In an effort to describe her supposed "cure" for homosexuality she wrote an essay, "I Am a Woman Again," for Ebony magazine in which she stated she had undergone an operation, which "helped change her life again.” She died of pneumonia in 1960, aged 52.