Gladys Bentley was born in Philadelphia in 1907 to a Trinidadian woman and an American man. She was the oldest of four children and, in her own words, neither wanted nor loved, because her mother had wanted a boy and was bitterly disappointed.
As a child, Bentley developed tender feelings for a female teacher and was often sent home for going to school in boys’ clothes. Her parents took her from doctor to doctor in an attempt to fix what they perceived as a deviation from traditionally feminine behaviour.
At sixteen, Bentley moved to New York. A talented singer and pianist, she was soon offered $400 by a Broadway agent to record eight tracks. But wanting to play to live audiences, Bentley also started filling in for unavailable entertainers in bars until one night she heard that the Mad House in Harlem needed a pianist. Even though they were looking for a male performer, she convinced the boss to let her play and wowed audience and owner to such an extent that she was immediately offered a regular contract.
In Harlem, Bentley was free to be herself. From the early 1920s to the mid 1930s, in what came to be known as the Harlem Renaissance, blacks and whites, homosexuals and heterosexual were brought together in Harlem by Prohibition and their joyous, alcohol-fuelled rebellion against it. It was the decade of the “New Negro”, when African Americans poured in from the whole country and became unprecedentedly prominent in literature, art, music and political debate.
Bentley thrived in such environment. She embraced her sexuality and “bulldagger” (or butch) identity and made it part of her performance. While as a blues singer she followed the trope of the down-on-her-luck woman mistreated by men, as a nightclub entertainer Bentley donned masculine outfits and haircuts, flirted with women, and performed sexually charged songs whose lyrics were often a rewritten, bawdy version of popular white ballads. She is considered one of the first drag kings, and impersonated that kind of mock, stereotyped masculinity that is typical of drag acts. However she did not try to pass for a man, nor was she preoccupied with concealing her love for women off the stage. Unlike other queer black female performers of the time, Bentley was open about her sexual orientation and at one point claimed to have married a woman.
Even though occasionally outraged, the public loved Bentley’s performance, her raucous act and lewd lyrics. From her first performance at the Mad House, Bentley’s ascent to fame was rapid and, for a while, unstoppable. She played in some of Harlem’s most famous clubs and speakeasies, such as Harry Hansberry’s Clam House and the Lafayette Theatre, and she recorded with a number of labels, including Okeh and Victor. As her popularity and her wages rose, she moved from Harlem to Park Avenue and enjoyed a degree of luxury she had never known before.
The financial crash of 1929 and the Depression that followed dealt a severe blow to Harlem, but Bentley remained popular throughout the first half of the 1930s, when, even after many of the clubs she used to sing in had shut down, she was still performing in Harlem’s Ubangi club.
In 1937 she moved to California, where she kept performing to enthusiastic audiences. However, the harassment she had occasionally experienced in Harlem for wearing men clothes and flaunting her sexuality intensified and in the 1950s the fear and paranoia of the McCarthy era stripped her of the assuredness of her early career.
In 1952, an article by Bentley titled “I Am a Woman Again” was published in Ebony magazine. Bentley claimed to have sought a hormonal treatment to enable her to love men the way she used to love women. The article is illustrated by photographs of her preparing the bed and dinner for her husband. One of them is captioned: “Miss Bentley enjoys [the] domestic role which she shunned for years.” Bentley claims to seek redemption and be looking for forgiveness, but some believe that she stepped back into the closet because she was worried about her career and the responsibility of taking care of her mother. She was briefly married to a man but it is likely that she kept having relationships with women.
In the 1950s while keeping on recording, Bentley became a prominent member of the Temple of Love in Christ Church, Inc and was ordained a minister. One of her last public appearances was on Groucho Marx’s TV show You Bet Your Life, where, now in a dress and with long hair, she claimed she had 500 songs at hand and showed the charisma and verve of her early years. She had just finished writing her memoir, If This Be Sin, but had not found a publisher.
She died of pneumonia in January 1960.