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Lesbian drag and male impersonation continue to exist as elusive aspects of queer history despite the contemporary popularization of drag queens. Rising out of Black working-class Harlem and performed predominantly by queer women, its performance has been subjected to layers of media erasure despite a prolific history. Gladys Bentley’s life and iconographic career are a testament to the early fortitude and magnetism of the art form’s pioneers.

“It seems I am born different.” Bentley would write reflecting on her decades-long career in an article for Ebony Magazine. Her formative years of becoming a nightlife legend are recounted in firsthand accounts, including none other than Harlem royalty Langston Hughes and, rightfully, her own.

Emerging at Harlem rent parties at just age 16, she’d grow to sell out speakeasy shows in the coming years. Leaving audiences dizzied by their own fascination with gender expression and sexual liberation—a microcosm of Harlem’s cultural revolution —she was the epitome of self-expression’s possibilities despite prohibition-era restlessness and Jim Crow-era morality politics.

With a voice warmly captivating sold-out audiences nightly, the shows, for many, grew akin to recognizing your reflection in the mirror for the first time. Beyond the expectations of well-mannered femininity was the allure of female masculinity that Bentley proved women could exude.

Expressing early romantic interest in a female schoolteacher and wearing her brother’s suits to class despite her family’s pleading, Gladys Bentley radiated the charm of nonconformity from the jump. In reaction to this, her mother took her “from doctor to doctor,” another cold shoulder in an already-strained mother-daughter relationship.

Much like her mother, it’s no secret these doctors didn’t have Gladys’ interest in mind; they were there to apply Freudian sexology morals of the 1920s. Newly naming and subsequently demonizing female homosexuality alongside its growing associations with masculine fashion and mannerisms.

"An atmosphere of whispering surrounded [her] in the house” as she grew into youth, she’d write. A suffocating feeling queer people know is a permeating call to leave. She was bursting at the seams of the life she was instructed to live and on the verge of living the one she dared to.

She’d make the leap, quickly coming of age amid Harlem’s prospering urban blues, exuding unmistakable niche and talent. Confidently gliding between speakeasy tables in a signature white-tailed suit, she’d serenade women with effortless wit. Crafting double entendres under gravitational tones of vibrato and scandalously turning out living room classics with newfound queer meanings. The songs’ original pronouns were swapped, unashamedly announcing her lesbian identity under ambient stage lighting.

Even in 1920s Harlem, despite many of its celebrated artists being remembered for their contributions to queer culture, speaking one’s queer identity out loud was still rather unheard of.

The blues genre in Harlem was radiant with possibilities for artists and listeners alike. Holding a long history of ingenuity, it became a medium for cultural liberation and sexual expression. Paving the way for Gladys Bentley to experiment with gender nonconformity and a lesbian identity through the genre’s plasticity. Lyrics reaching into a future where one might exist comfortably in multitudes of queerness.

Her article for Ebony magazine was curiously titled “I Am a Woman Again.” In which Bentley writes her life story through both legacy and repentance. Chalking up her initial belief in being “born different” to a misunderstanding.

She’d state, “In later years I learned that ‘different’ people are made, not born.” Her personal narrative was becoming more consistent with Freudian sexologists rather than the visceral understanding of queerness she’d long ago formed in childhood. The condemning new take on her life story conceivably stemmed from many pressures central to the McCarthyism era, specifically that of gender and sexual conformity.

It was a personal history written as two stories at once, the gallant former life still shining through beneath the post-war conservatism of the 1950s. The article’s clipped photos sit in that contradiction, featuring her displaying a younger self in extravagant drag and smiling as wide as in her speakeasy days as she held up the album for the camera.

Author James F. Wilson parallels Gladys Bentley’s “I Am a Woman Again” article to the cultural uproar that Radclyffe Hall’s The Well of Loneliness created in establishing the model of a masculine lesbian identity.  Whether Bentley fulfilled the archetype of Stephen, the book’s main character, after thorough reading or simply produced her “mannish” demeanor by coincidence is unclear. There is certainly merit in the fact that Bentley nearly replicates the psychoanalysis of Stephan’s character’s queerness, summarized by an unloving mother disappointed that her daughter wasn’t born a son. Bentley’s own mother assumed all girls were “fated for trouble,” a justification for emotional withholding.

Both Bentley’s career and Hall’s novel would reach a fever pitch in 1928. Their concurrent stories of maternal neglect easily fit into the sexologists’ depictions of unloving and emotionally unavailable mothers being used as an explanation for “sexual inversion.” The environmental narrative here explains away their lesbian identity as something fixable, a fault of one’s upbringing, and not innate. Gladys’ story is relatively convincing to an audience primed to expect heterosexuality as the standard outcome, adorned with pictures of her living a domesticated life and telling the love stories of back-to-back marriages to men.

Late into her career and in traditionally feminine attire, Bentley is seen performing the Billie Holiday number “Them There Eyes” in the only stage footage of her to exist. Dropping the signature Gladys Bentley iconography and promoting a recent biography of hers titled “If This Be Sin” in her introduction.

The video then flips to Bentley taking hold of the piano, the room filling with her stunning rolling tone. Keys pounding a waltz of the song through to an image of a larger history not recorded: once handsomely dressed to the nines in her white-tailed suit and slicked-back hair, her voice buzzing well into dawn’s break. Crescendoing at the words, “they sparkle, they bubble” during the Holiday cover, she ecstatically slips into the lyrics, “gets you in a whole lotta trouble”–all but winking at the other two stage members.

The rebellion of the words, a tasting note of her earlier performances, eyes widening with elation so quick the unsuspecting guest might miss it. A gaze that says she once knew the feeling those words evoke intimately; the adrenaline in understanding the threat posed by laughing in the face of the status quo and doing it anyway.

Closing my eyes, the recording plays on; I see the late 1920s, her career’s peak. The background dancers are synchronous in the speakeasy haze, floorboards ricocheting the innuendos as one foot leads rhythm, the other commanding the pedals. Governing the stage, not as a man, a woman, or an impersonator, but as Gladys Bentley herself, unsatisfied with the neat stipulations of labeling her act.

Moreover, she’d face labeling through degrading program bills written to dehumanize her act. Terms like “bulldagger,” a racialized lesbian slur, were being used at length, and descriptions such as “Brown Bomber of Sophisticated Songs” targeted Bentley’s image and right to perform. The intersection of her identity as a Black gender-nonconforming lesbian, stirring the distorted fears of those who could benefit from her leaving the limelight or making herself small.

It was a time of rapid social change, one where those outside Harlem would flock to its streets with a growing hunger that polite society couldn’t satiate. Though after their quick fix, the neighborhood often remained only a spectacle in their minds, still inebriated with etiquette morals saturated in racism and intersecting class biases.

The withstanding of social cruelty Bentley endured throughout a lifetime would be enough to leave anyone depleted. Without a foundational community or those who can bear witness to our inner lives and not just our performance, it’s possible she confided in a life where she’d be guaranteed support.

Reading the Ebony article, I couldn’t help but feel something was missing, left wishing for one last quote or explanation from Bentley herself. The stark contrast in abandoning all traces of a fearless former image for traditional domesticity. No space for the person she once was. The pages adorned with pictures of her eyes averted and head down, completing household tasks, a cold contrast to the larger-than-life presence in her Harlem days.

Despite the article's intended finality, there remains a brief but revealing firsthand account from a friend in her final years. Upon visiting Bentley's home, two photographs rested side by side. She would confide that one contained an image of her husband, the other of her wife.

Many wrote in response to Bentley’s article and the new adoption of heterosexuality. One man particularly resonated with her story, not its thesis but rather the feelings it stirred. He’d share, “I know what she meant when she spoke of having lived a personal hell. I’m still living it…why there is so much contempt for us I do not know.”

It becomes evident that Bentley’s largest qualm with living as openly queer was how lonely it becomes forced to live on the periphery of society. Her condemnation of others pursuing the life was a grave warning of what she endured, a possible desire to protect them from hardship before there was safety to be found in the organized queer community.

Though the article’s inception was likely in conjunction with social coercion and its foul play, it gives us insight into the unique perseverance of Bentley’s lifetime. She’d pass early in life at age 52, leaving some threads unanswered.

What’s to be remembered is the Gladys Bentley the world came to adore, in all her life’s debuts, her artistic resistance on Harlem’s stage of unabridged importance to the enduring and ever-evolving timeline of queer history. She was a visionary for what living an openly queer life could mean, and her legacy is a reminder of how to exist before permission is granted.