This Women’s History Month, as women and queer people in the United States face growing challenges to their bodily autonomy, it’s encouraging to turn to audacious women from the past who also lived through challenging times. My forthcoming book, The Famous Lady Lovers: Black Women and Queer Desire Before Stonewall, is filled with stories of women who surmounted life in the Jim Crow era to craft the relationships they desired, and Gladys Bentley was one of the boldest of them all.

Bentley was the most popular and infamous speakeasy performer in Prohibition-era New York. A large, masculine, Black woman—a “bulldagger,” in the language of her day—she was known for wearing a white tuxedo and top hat onstage while expertly playing the piano and singing dirty versions of popular songs to rapt “slumming” audiences. She even married her white girlfriend in a well-publicized Atlantic City wedding ceremony.

There is a rich history of “male impersonators” on the popular American stage going back to the 19th century, who today are often known as “drag kings.” Some of these performers actively crafted male personae, but others like Bentley used the category of male impersonator just to be their masculine selves, on and off the stage.

In the 1920s, lesbian identity was just becoming visible in America popular culture, but it was still generally viewed as immoral, criminal, and akin to a mental illness. Despite this, Bentley was able to make a successful living being her openly queer self, a rarity for the time. She made sapphism more visible in a time of changing ideas about sex and gender, as women were entering more professions and having fewer children.

Her performances often involved going into the audience and flirting with all the female patrons. One reviewer wrote she “sang wicked blues in a deep contralto voice” and “bemoaned her girlfriend who had deserted her for another woman.” As Bentley sang, she went from table to table, and “much to the delight of the audience, every once in a while she’d feign recognition only to find disappointment upon closer inspection.” As for her bawdy songs, one included the lyrics, “It’s a helluva situation up at Yale / As a means of recreation / They rely on masturbation / It’s a helluva situation up at Yale.”

The early 20th century was still a conservative time in many ways, but the banning of alcohol from 1920 to 1933 created illicit spaces in northern cities like speakeasies and rent parties, which offered temporary freedom from social norms. Hundreds of thousands of Southern African Americans went to these cities in search of new opportunities, in what became known as the Great Migration. And Black soldiers who had served in World War I came home with a renewed sense of racial pride. This led to an explosion of Black literature, music, art, and performance often referred to as the Harlem Renaissance. All these factors helped make Harlem the epicenter of the era, where Gladys Bentley rose to fame.

Born in 1907, Bentley relocated to New York from Philadelphia as a teenager after her parents kicked her out for being queer. Incredibly talented on the piano, she soon started performing professionally. By the late 1920s, she was so successful that for a while she had a Harlem club named after her, not to mention a Park Avenue apartment, servants, and a beautiful car.