Sometimes, the line between "drag artist" and "performer who is queer" becomes incredibly blurry and hard to define.
One of the most famous queer artists of the Harlem renaissance was Gladys Bentley, who was openly a lesbian and who wore men's clothing as a part of her stage persona.
Bentley sometimes used the term "male impersonator" as a way of being able to wear masculine attire on stage, but she was never fully pretending to be male. She was always being herself.
A virtuouso piano player, she was called "America's Greatest Sepia Piano Player" and the "Brown Bomber of Sophisticated Songs" She headlined at places like Cotton Club and the Ubangi Club, and always drew in massive crowds.
Described by Langston Hughes, "For two or three amazing years, Miss Bentley sat, and played piano all night long … with scarcely a break between the notes, sliding from one song to another, with a powerful and continuous underbeat of jungle rhythm. Miss Bentley was an amazing exhibition of musical energy – a large, dark, masculine lady, whose feet pounded the floor while her fingers pounded the keyboard – a perfect piece of African sculpture, animated by her own rhythm."
Gladys Bentley was far from being the only queer woman blues singer of the day. Lucille Bogan, Bessie Smith and Ma Rainey also had sexual relationships with women, and sang songs about same-sex desire and "bulldaggers."
Even still, Bentley stood out for her unabashed queerness. When performing at the Ubangi Club, she had a chorus line of drag queens performing behind her.
As time wore on and America became more conservative, Bentley's career struggled. In the 1950s, she renounced her old ways and claimed she had been "cured" of lesbianism and "become a woman again" through a regimen of estrogen shots. It was the only way she was able to maintain a career through the McCarthy era.