Hailed as “an amazing exhibition of musical energy” by Langston Hughes, Gladys Bentley was a notable blues singer and provocateur.

In 1923, Bentley started her musical career as a teenager in Harlem, where she would play the piano at rent parties during the Prohibition era. In addition to being an impressive pianist, Bentley made her mark by performing covers of hit songs with gender-bent and explicit lyrics.

Bentley’s career took off in the late 1920s, when she was able to make it big on the nightclub circuit. She performed at the iconic gay speakeasy the Clam House and headlined at the Ubangi Club in the early 1930s, where she often performed with drag queens.

Throughout her career, Bentley was known for pushing the boundaries of race, gender and sexuality. She was famous for sporting a white tuxedo and top hat and having a raspy alto voice that meshed well with her suggestive lyrics. Bentley was also known to flirt with women in the audience.

Bentley’s rise to fame was a combination of talent and her unique ability to spin the press in her favour. Bentley would tell gossip columnists about her lesbian identity as a form of shock value, including a rumoured, and unofficial, marriage between herself and a white woman.

At the height of her career, Bentley was reportedly one of the highest-paid Black women in the U.S., but the end of Prohibition and the beginning of the Great Depression would curtail the artistic output of the Harlem Renaissance.

And due to the rise of McCarthyism in the 1950s, Bentley disavowed her queerness to salvage her career. In 1952, Bentley published the essay “I Am a Woman Again” in Ebony magazine, where she claimed she was “cured” of her lesbianism and that she was married to a man.

Bentley died in 1960 at the age of 52 due to pneumonia complications, but she is remembered today as a gender outlaw and reinventor during a time that wasn’t quite ready to accept her.