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 signaturetuxedo 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.