Women’s History Month: Gladys Bentley


Born in Philadelphia in 1907, Gladys Bentley didn’t push boundaries as much as she obliterated them.

Bentley was a pianist, a blues singer, an entertainer, and a provocateur. Later in her life, during an interview with Ebony magazine, she stated that “It seems I was born different. At least, I always thought I was.” As a child, she shunned dresses and wore her brother’s suits. She had crushes on her female teachers. Her behavior was deemed “unladylike” and, wanting to “cure her”, her family sent her to doctors. Finally, at the age of 16, Gladys ran away to NYC.

She eventually made her way to Harlem, where, for a while, she made a living as an entertainer at “rent parties”. Her big break came when she answered an ad for a pianist.

The only problem? The ad specified a male pianist.

Gladys wasn’t going to let that stop her. In fact, according to some accounts, that’s when Gladys began performing in men’s clothing: “white full dress shirts, stiff collars, small bow ties, oxfords, short Eton jackets, and hair cut straight back”.

And thus, a star was born.

The Harlem Renaissance was a massively important time in American art, literature, theatre, music and intellectual thought. And Gladys, in the middle of it all, navigated her way through as a woman, on her own terms. Dressed in men’s attire, she performed at some of the hottest clubs of the era, like The Cotton Club as well as the gay speakeasy The Clam Club. She “sang raunchy songs laced with double-entendres that thrilled and scandalized her audiences.”, and flirted with women in the audience. Oh, and she was often backed up by scantily-clad male dancers, sometimes in drag.

She was, what one observer described as a “masculine garbed smut-singing entertainer”

What’s not to like, right?

She was also wildly popular, not just with Black Harlem residents, but with white customers who would head uptown to let their hair down. At the height of her Harlem popularity, Gladys made enough money to live on Park Avenue, and at one point, spilled some serious tea: she’d married a white woman in a civil union.

There was a lot going on in the 1920 and 1930s. A LOT.

For all we think about views of sexuality and gender progressing on a linear timeline, they really haven’t. Right now, in 2021, where we are still fighting to recognize trans rights, gender diversity, and same-sex equality, it seems bizarre to think that a century ago, folks seemed a hell of a lot more progressive than they do now.

But in some ways, they were.

But all good things must come to an end, right?

By the end of the 1930s, prohibition had ended, and the club circuit started to fade. Gladys moved to California and “continued recording music, touring and performing in upscale supper clubs and bars,” though with a much toned-down version of her earlier shows.

And then the 1950s–that aberration of a decade–came a calling, dragging McCarthyism in its wake. And the US went from a time when Black and white customers sat together drinking hooch listening to a gay, Black woman dressed in a tux sing dirty songs, to a time when even the whiff of being gay was lumped in with communism and other things considered “Un-American”. Gladys, always savvy to the court of public opinion, or perhaps merely as a means of self-preservation, started wearing dresses, and claimed to have rediscovered her “womanliness”. She alleged to have married a man (who later denied it). Whether or not she was playing a role to avoid persecution is hard to know. Or perhaps Gladys was living her best life the whole damn time, however she saw fit, wherever, however, and with whomever.

She was, as author Jim Wilson refers to her, a “gender outlaw” who was “just defiant in who she was”.

In 1960, Gladys Bentley died of pneumonia, aged 52.

There are a lot of historians who predict we will see a resurgence of the “roaring 20s” in our post-Covid era, living big and bold lives to their fullest.

I think Gladys would have liked that.

Happy Women’s History Month!

Talk to me, Goose.

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