14. Gladys Bentley, Performer

Gladys Bentley was an immensely talented gender-bending icon of the 1920s and 1930s Harlem. An open lesbian, Bentley belted out feminist anthems and flirted with women in the crowds at her shows, prompting them to sing raunchy lyrics at her in return. She was one of many queer and gender-bending black performers in the Harlem art scene. Sadly, with the rise of McCarthyism, she underwent hormone “gay conversion” type treatment to attempt to be heterosexual out of fear of blacklisting or worse.



