Gladys Alberta Bentley
Her career as a singer, pianist and entertainer saw a boost in the 1920s when she appeared at Harry Hansberry’s Clam House in New York in the 1920s, as a black, lesbian, cross-dressing performer. Bentley was well noted for her signature tuxedo and top hat and her deep, growling voice while flirting with women in the audience. When speakeasy in Harlem declined, the openly lesbian entertainer moved to California where she was billed as “America’s Greatest Sepia Piano Player” and the “Brown Bomber of Sophisticated Songs”. Yet, for wearing men’s clothing, she regularly came under attacks and criticisms and this affected her musical career. She would later start wearing women’s clothes before getting married.