Gladys Bentley: greatest lesbian singer you never heard of

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Gladys Bentley

On December 30 1947, North Hollywood’s Doll House advertised the risk-gay Gladys Bentley as their entertainment for the following night. It was no doubt one hell of a New Year’s Eve party.

Gladys Bentley was one of the most memorable live acts ever to tread a stage. She sang, danced, cracked jokes, and flirted with the audience – well, the women, anyway.

The Valley Times reported that Gladys would perform some of the cheekier original numbers she’d so far held back. Gladys wrote her own innuendo-laden lyrics to the popular tunes of the day. She designed the choruses for audiences to sing along.

Risqué, they called her act: sexually suggestive and liable to shock. Hence the Doll House’s wordplay: risk-gay. Gladys was risqué, and she was gay.

Gladys Bentley

Born in 1907, Gladys Bentley realised she was a lesbian at a young age. After her parents took her to doctors looking for a ‘cure’, she ran away from home at 16. She arrived in Harlem during Prohibition, a time of bootleg liquor and riotous speakeasies.

Initially, Gladys performed at ‘rent’ parties. People needing money for rent charged admission and laid on entertainment, food and alcohol.

After working up her act, she auditioned at an illegal gay bar advertising for a male pianist. As she later wrote, she convinced the club owner she was the equal of any male pianist.

“The boss was reluctant to give me a chance. I finally convinced him. My hands fairly flew over the keys. When I had finished my first number, the burst of applause was terrific…

“One of the unique things about my act was the way I dressed. I wore immaculate full white dress shirts with stiff collars, small bow ties and shirts, oxfords, short Eton jackets and hair cut straight back.”

Soon one of the hottest acts in town, Gladys also became one of the highest-paid. She lived for a while with a wealthy girlfriend in a Park Avenue penthouse and, in 1928, married another woman. She told a newspaper gossip columnist about her marriage.

“Well, who’s the man?”

“Man?” laughed Gladys, “It’s a woman.”

Big, Black, undoubtedly Beautiful, and Butch AF

But her success also attracted unfavourable attention. Gladys was defiantly herself, and that always pisses off defenders of the status quo.

She was Big, Black, undoubtedly Beautiful, and Butch AF, a ‘bulldagger’ in the lingo of the day. But she made no attempt to pass as a man. She wore heavy stage makeup, and her tailor-made tuxedo highlighted her bust. She was proudly and loudly a lesbian.

During Prohibition, a single complaint could lead to the demise of a club. They all operated illegally. Following a complaint about a ‘masculine garbed smut-singing entertainer’, the cops chained the doors shut on one venue where Gladys performed.

Even as the headline act of a lavish review, she risked closure with whingers whining about her suggestive lyrics, but also this time about the ‘pansy’ lineup. Gladys was performing with a chorus line of twenty female impersonators.

In 1937, she moved to San Francisco. She worked on and off at Mona’s, a lesbian bar established in 1934. She also toured. The owner of the Doll House told the papers, it took three years of trying before he managed to book Gladys Bentley for his venue.

McCarthy era

Post-WWII, Gladys struggled to find the same high-paying gigs. Persecution during the McCarthy era deterred venues from employing ‘deviants’.

Gladys adapted. In 1952, she authored a feature article in Ebony Magazine titled ‘I Am Woman Again’. She basically renounced lesbianism and claimed to be ‘normal’ following an operation and hormone treatment.

Scholars differ over whether Gladys Bentley actually underwent some form of conversion therapy or simply ‘played’ the press in order to continue her career.

In 1958, she appeared on Groucho Marx’s You Bet Your Life TV show (below). Sadly, she died of influenza a couple of years later, at just 52 years of age.

Gladys Bentley knew her way around words. She wrote her own lyrics, and by the 1950s, her repertoire included over 500 songs.

So, it’s worth looking at a few sentences the talented wordsmith wrote in that 1952 article. They lead this writer to think Gladys Bentley still knew exactly who she was. But she also recognised the role she needed to play to resurrect her career.

“Some of us wear the symbols and badges of our non-conformity. Others, seeking to avoid the censure of society, hide behind respectable fronts, always haunted by the fear of exposure and ostracism. Society shuns us. The unscrupulous exploit us. Very few people can understand us. In fact, a great number of us do not understand ourselves.”


Read about more famous lesbians from the past.

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Destiny Rogers

Destiny Rogers embarked on her career in the media industry immediately after high school, initially joining Mirror News, which later evolved into News Ltd. She fondly recalls editing Ian Byford's 'Passing Glances: A History of Gay Cairns' as one of her most fulfilling projects. Additionally, Destiny co-researched and co-wrote 'The Queen's Ball', chronicling the history of the world's longest-running continuous queer event. Her investigative work on the history of Australia's COON Cheese and Edward Coon culminated in the publication 'COON: More Holes than Swiss Cheese', a collaborative effort with Dr. Stephen Hagan. Destiny's journey at QNews began as a feature writer, and she was subsequently elevated to the role of Managing Editor of QNews Magazine in 2018. However, in July 2022, she decided to resign from this role to refocus on research and feature writing. For contact, please reach out at

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