The amazing Gladys Bentley (August 12, 1907 – January 18, 1960) was an American blues singer during the beginning of Harlem’s Renaissance in the 1920’s.Bentley was born in Philadelphia, Pennsylvania, the daughter of American George L. Bentley and his wife, a Trinidadian, Mary Mote. She appeared at Harry Hansberry’s Clam House on 133rd Street, one of New York City’s most notorious gay speakeasies, in the 1920s, and headlined in the early thirties 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 white tuxedo. shoes, cane and top hat), played piano, and sang her own raunchy lyrics to popular tunes of the day in a deep, growling voice while flirting outrageously with women in the audience.
On the decline of the Harlem speakeasies with the repeal of Prohibition, she relocated to southern California, where she was billed as “America’s Greatest Sepia Piano Player”, and the “Brown Bomber of Sophisticated Songs”. She was frequently harassed for wearing men’s clothing. She claimed that she had married a white woman in Atlantic City.
Bentley was openly lesbian during her early career, but during the McCarthy Era, she started wearing dresses, married a man at the age of 28 named Charles Roberts. Charles Roberts was a cook who she married (within 5 months of meeting) in a civil ceremony in Santa Barbara, CA in 1952. Mr. Roberts later denied that they ever married.
Bentley also studied to be a minister, claiming to have been “cured” by taking female hormones. In an effort to give more knowledge about her “cure” she authored an Ebony magazine story called “I am a woman again”, in which she stated she had undergone an operation, which “helped change her life again”.She died, aged 52, from pneumonia in 1960.
Fictional characters based on Bentley appeared in Carl Van Vechten’s Parties, Clement Woods’s Deep River, and Blair Niles’s Strange Brother. She recorded for the OKeh, Victor, Excelsior, and Flame labels.
Here she is performing on Groucho Marx‘s “You Bet Your Life” show – love her back and forth with Groucho: