Bawdy Facts About Gladys Bentley, The Dapper Diva

January 28, 2021 | Dancy Mason

Bawdy Facts About Gladys Bentley, The Dapper Diva

In the 1920s, speakeasies ruled New York City, and Gladys Bentley ruled the speakeasies. Inside these hidden, smoky rooms, Bentley astounded and scandalized audiences with her booming voice, her impeccably tailored suits, and her raunchy lyrics. But once the lights went down, no one knew the tragedy going on behind the scenes. Here are bawdy facts about Gladys Bentley.

Note: Although some historians view Bentley as a trans-masculine figure, she used she/her pronouns throughout her life. This article reflects that.

Gladys Bentley Facts

1. Her Mother Rejected Her

Gladys Bentley came into this world on August 12, 1907 as the eldest child of George Bentley and his wife Mary Mote. But trouble started as soon as Gladys was born. Her mother had desperately wanted a boy, and when the nurses told her she had a little girl instead, the matriarch refused to even touch her baby. It only got worse from there.

Gladys Bentley FactsWikimedia Commons


2. Her Childhood Was Tragic

Gladys’s mother never seemed to get over the shock of having her firstborn be a daughter. When she brought little Gladys home, she refused to nurse the girl, leaving Bentley’s grandmother to raise the infant on a bottle for six months. Eventually, Gladys grew old enough to notice this icy upbringing—and the consequences were devastating.

Gladys Bentley FactsPxHere

3. She Learned To Hate Men

According to Bentley herself, her dysfunctional relationship with her mother shaped the rest of her life in intense ways. She began to resent her brothers and didn’t want men to touch her, yet she also started wearing boys’ clothes and suits instead of skirts and blouses, partly in a bid to emulate who her mother wanted her to be. Well, it backfired.

Robert Johnson FactsShutterstock

4. She Was “Unladylike”

Though Bentley was in the process of finding herself, these discoveries only made her family more disgusted with her. Already a big girl, her parents and siblings saw this masculine turn as shamefully “unladylike,” while her classmates teased her at school. Fed up and at the brink of her sanity, Bentley resorted to drastic measures.

Clara Barton FactsShutterstock

5. She Made A Great Escape

Even as a teenage girl of 16, Bentley had grown into a headstrong young woman, and she was sick and tired of feeling rejected. So she did what many 16-year-olds only dream of: She ran away from home to go seek stardom in Harlem, New York, the epicentre of Black bohemian culture at the time. What she found was absolute infamy.

Gladys Bentley FactsWikimedia Commons

6. She Had “Forbidden” Desires

When Bentley ran away from home, she was certainly disillusioned with her family—but she was also hiding a huge secret. Since she was a schoolgirl, she had started daydreaming about her female teachers, and developing intimate feelings for the women she knew. At the time, she didn’t understand her desires…but all that was about to change in a big way.

Gladys Bentley FactsAmerican Masters, PBS

7. She Went To Secret Parties

The teenage Bentley was in way over her head when she moved to Harlem, and she needed to find work, stat. Her beginnings weren’t humble, though; they were scandalous. She started to perform at prohibition-era “rent parties,” soirees that charged guests a fee to come enjoy a house party with booze and entertainment. Still, Bentley had bigger dreams on her mind.

Adelaide Hall factsGetty Images

8. She Had A Hidden Talent

Eventually, Bentley got tired of performing for small crowds, and began looking for gigs at bona fide clubs around New York. She found one, alright. She’d always been good at the piano, and heard through a friend one night that the notorious gay speakeasy the Clam House was looking for a pianist. There was just one huge problem.

Gladys Bentley FactsShutterstock

9. She Gave A Virtuoso Performance

See, the Clam House was actually looking for a male pianist. Think this stopped Gladys Bentley? Heck no. She marched right over one night during a packed audience and met the club’s skeptical boss, Harry Hansberry. Then she proceeded to blow his mind. As Bentley put it, “My hands fairly flew over the keys.” And the response was legendary.

Gladys Bentley FactsShutterstock

10. She Brought An Audience To Their Knees

When Bentley finished her performance, the room burst into applause. They’d seen talent before, but they’d never seen talent like this. According to Bentley, one of the white customers came over, placed a crisp five-dollar bill in her hand, and begged her to play something else, saying, “We don’t care what it is. Just play.” And Bentley was just getting started.

Gladys Bentley FactsPxHere

11. She Had A Signature Style

Gladys Bentley had waited years for this moment, and she wasted no time grabbing the opportunity with both hands. She changed her stage name (briefly) to Barbara “Bobbie” Minton, and upgraded her clothing style to "white full dress shirts, stiff collars, [and] small bow ties” with a signature top hat. It wouldn’t be long before she shot to fame.

Gladys Bentley FactsAmerican Masters, PBS

12. She Had A Big Claim To Fame

Within weeks of starting her gig at the Clam House, Bentley transformed the whole joint—literally. Audience members started raving about her stage presence at the piano, so much so that the club even changed its name to “Barbara’s Exclusive Club” to take the most advantage of Bentley’s fame and notoriety…while they still could.

Gladys Bentley FactsShutterstock

13. She Performed At A Notorious Venue

Gladys Bentley wasn’t just popular with the common people; she had all of New York eating out of the palm of her hand. Her performances at the Clam House attracted luminaries like poet Langston Hughes and the photographer Carl Van Vechten, who both sang her praises. After a long climb, Bentley had finally made it to the top—but with stardom came scandal.

Gladys Bentley FactsWikimedia Commons

14. She Had Expensive Tastes

Bentley always had expensive tastes; she just never had the bank account to match. That all changed in the blink of an eye. When she eventually left the Clam House for the swanky Ubangi Club on Park Avenue, she reportedly rented an extravagant penthouse apartment that would have raised her mother’s eyebrows. Then again, there were rumors that would have made her mother straight-up faint…

Justin Timberlake factsGetty Images

15. She Took Scandalous Lovers

Gladys Bentley knew how to live life to the fullest, and with her large, bodacious build and flashy sense of style, she had no problem getting women to fall into bed with her. Some even claimed that her infamous penthouse, complete with a coterie of servants and a car, actually belonged to one of Bentley’s rich lesbian lovers. Get it, Gladys.

Brenda Frazier FactsWallpaper Flare

16. She Kissed And Told

Thing is, Bentley didn’t keep her private life private, not by a long shot. Her songs revealed all her dirty little secrets. When she got up on stage every night in her top hat and tails, she sang loud and proud about “sissies” and “bulldaggers,” and her lyrics often illustrated her lesbian affairs in very explicit terms. And she didn’t stop there.

Gladys Bentley FactsShutterstock

17. She Was A Dirty Girl

Want just a taste of Gladys Bentley’s scorching lyrics? Try this on for size: For one of her sweatiest performances, Bentley combined the titles and lyrics of the popular songs “Sweet Alice Blue Gown” and “Georgia Brown” to make one mightily controversial ditty about—er, how do I put this—the backdoor bedroom act. Yow.

Gladys Bentley FactsAmerican Masters, PBS

18. She Seduced Her Fans

One of Bentley’s signature performance moves was to flirt shamelessly with women in the audience. This happened even at her star-studded Hollywood shows, which would have the likes of Mary Astor and Barbara Stanwyck watching from the audience. The best part? When Bentley came up to a hot young thing, she had one go-to move…

Barbara Stanwyck FactsWikipedia

19. She Had A Go-To Pickup Line

When Bentley approached young, impressionable women at her clubs, she would often get them in the mood by asking them to sing dirty lyrics into her microphone. No doubt, Gladys Bentley won a fair few beautiful conquests in her day by picking them out of the crowd and mixing business with pleasure. Heck, I volunteer as tribute.

Gladys Bentley FactsShutterstock

20. She Had A Scandalous Marriage

In 1931, Gladys Bentley was at the top of her game, and was one of the most sought-after performers—and lovers—in the United States. So, she went ahead and did something truly scandalous. That year, she claimed that she married an unknown woman in a civil ceremony in Atlantic City, a practically unheard-of move. On top of that, the news got out in a sensational way.

Gladys Bentley FactsShutterstock

21. She Loved To Gossip

At the time, the comings and goings of Bentley’s inner boudoir were public knowledge, and that was just how she liked it. In fact, she was often the source. It was Bentley who told a gossip columnist that she’d just tied the knot. Even better, when the columnist asked, “Well, who’s the man?” Bentley’s reply was oh-so-satisfying. She scoffed and said, “Man? It’s a woman.”

Gladys Bentley FactsShutterstock

22. She Was A Bad Girl

Bentley didn’t do anything by halves. So when it came to her unnamed paramour, it wasn’t just that she took a woman as her wife that raised people’s eyebrows. According to the stories, Bentley’s new partner was also a white woman. Yep, Bentley did that, and in the middle of segregated America to boot. Her biggest dramas, however, were yet to come.

Gladys Bentley FactsAmerican Masters, PBS

23. She Got Kicked Out Of A Nightclub

With lyrics like hers, controversy came knocking on Bentley’s door soon enough. While performing at the Manhattan nightclub King’s Terrace, the “masculine garbed smut-singing entertainer,” as one audience member put it, quickly got the authorities to shut the whole place down with her performance. Looking back, this might have been a bad omen.

Gladys Bentley FactsAmerican Masters, PBS

24. She Chased Stardom

By 1933, Bentley had parlayed her fame into country-wide domination. She had a recording contract for her raunchy songs, put out a series of records with her broad, booming voice, and was just positioning herself to take over the bright lights of Broadway. It couldn’t have been going better…but a rapid downfall was just around the corner.

Robert Johnson FactsShutterstock

25. An Old Friend Dealt Her A Cruel Betrayal

Just as Gladys Bentley was taking center-stage on Broadway, her old Clam House boss Harry Hansberry came out of the woodwork to ruin her life. Jealous of her immense success and the fact she’d moved on from his club, Hansberry sued her, claiming she hadn’t completed her contract with him. And then he went after everything she held dear.

Best day on the jobUnsplash

26. She Landed In The Supreme Court

Hansberry was so vengeful, he wasn’t content to just sue Bentley; he also tried to prevent her from seeking any further success. He demanded she stop trying to perform on Broadway, and took his suit all the way up to the Supreme Court. Once more, I ask: Did Gladys Bentley care? Heck no. She went to Broadway anyway—but she would live to regret it.

Joan Rivers factsNeedpix

27. The Crowds Turned On Her

Bentley made her spectacular debut on the Great White Way in 1933…until it turned into an utter disaster. She’d made a scandalous name for herself singing her dirty songs, and audiences came out in droves. But they weren’t all there for the right reasons. Some pearl-clutching patrons complained, and the city’s response was swift and brutal.

Gladys Bentley FactsGetty Images

28. She Was Public Enemy Number One

Within months of Bentley’s entrance into Broadway, the authorities had cottoned onto to her risqué shows, and they made sure to nip them right in the bud. When Bentley showed up for a given performance, she’d soon find that officers had locked up her venues in an attempt to drive away her business. The ploy worked a little too well.

Princess Alice of Battenberg FactsShutterstock

29. She Had A Failed Comeback

By 1934, just a year after her debut, Gladys Bentley had to give up on her Broadway baby dreams, and she slunk back to Ubangi Club with her white coat tails between her legs. Yet although the singer still brought the house down, her comeback only lasted three short years. Before long, Bentley’s world got turned upside down again.

Gladys Bentley FactsYou Bet Your Life, NBC

30. She Experienced A Tragic Downfall

When prohibition ended in the 1930s, it was a slow, painful death for Bentley’s career, and her speakeasy gigs started to dry up as booze flooded the public markets. Inevitably, even the vaunted Ubangi club closed its doors in 1937, kicking Bentley out along with its regular clientele. The performer had survived a harsh life up until this point, but she was about to spiral out of control.

Winston Churchill factsWikimedia Commons

31. She Tried To Rebrand Herself

Oh, Bentley tried her best to make it work—and it almost did. She relocated to southern California, marketing herself as “America’s Greatest Sepia Piano Player” and “The Brown Bomber of Sophisticated Songs,” a cheeky nod to her inelegant lyrical double entendres. Yet in California, Bentley only got into some silver screen drama.

The Beach Boys FactsFlickr

32. She Was An Outlaw

While Bentley was in California, the halcyon days of the liberal Roaring Twenties transformed into conservatism almost overnight, and she didn’t find as many friendly faces in her crowds. Suddenly, she had to get a special permit to wear men’s clothing for her performances, and endured heckling on the streets. Maybe that’s why things took a turn for the tragic…

Gladys Bentley FactsShutterstock

33. She Married A Surprising Person

While in Los Angeles, Bentley was up to her usual tricks in the beginning—frequenting and performing at gay bars and scoping out beautiful new lovers. Then, she made a jaw-dropping decision. Bentley, who never seemed to look at a man before, married the very manly J.T. Gipson shortly after arriving on the West coast. Was Bentley slowly unraveling? Well, just you wait.

Gladys Bentley FactsAmerican Masters, PBS

34. She Wrote A Tell-All Article

In the summer of 1952, while married to Gipson, Bentley penned an article for Ebony magazine looking back on her stardom and her personal life. The headline sent shockwaves through America. “I Am A Woman Again,” Bentley declared, disavowing the gender-bending performances that had made her famous. And that was the least of her revelations.

Horrible First Impressions FactsUnsplash

35. She Made A Heartbreaking Confession

“I Am A Woman Again” is a fraught, heartbreaking artifact of Bentley’s life. In it, she not only repudiates her homosexuality, but also her entire identity before that moment, revealing that she now only wears dresses and other acceptable housewife attire in order to please her husband and herself. Sadly, Bentley’s confessions don’t stop there.

Gladys Bentley FactsAmerican Masters, PBS

36. She Went To Drastic Measures

Not content with changing her outward appearance, in the 1950s Bentley began to change her insides as well, going to a doctor and beginning to take female hormones to “overcome” her more masculine traits. Bentley was so desperate to change, she submitted to the expensive injections three times a week for an entire half a year.

Gladys Bentley FactsShutterstock

37. She Had A Steamy Romance

By the 1950s, Gladys Bentley was making some even more rash decisions. In 1952, her first husband J.T. Gipson passed, but the spitfire performer didn’t wait until he was cold in his grave to jump into bed…with yet another man. That year, Bentley took up with kitchen cook Charles Roberts, marrying him after a whirlwind courtship. It did not end well.

Gladys Bentley FactsAmerican Masters, PBS

38. She Liked Younger Men

The red flags were there from the start when it came to Charles Roberts. For one, while Bentley was a full-grown woman at 45 years old, Roberts was a measly 28 years old and not a match for her or her outsized reputation. So maybe it’s no surprise that the lovebirds split up less than a year into their relationship—and more heartache was to come.

Babe Paley FactsShutterstock

39. Her Lover Accused Her Of Lying

Whatever her reasons for marrying men, Gladys Bentley sure didn’t know how to pick them. By some accounts, Bentley’s marriage with Roberts was brief and tragic, but according to Roberts himself, it didn’t happen at all. Yep, the young cook later denied ever having a wedding ceremony with the singer. That one had to hurt.

Elizabeth of Russia FactsShutterstock

40. She Made A Huge Sacrifice

For all her revelations in her Ebony article, Bentley’s confessions may not be what they seem. Today, experts believe that the article and her marriages were not actually true representations of her identity, but rather her attempts to conform to the newly conservative standards of the day so she could survive. Or there might have been a more cynical reason…

Gladys Bentley FactsAmerican Masters, PBS

41. She Did Anything For The Limelight

Gladys Bentley was a consummate show woman, and she simply didn’t know how to let a publicity opportunity pass her by. Some have argued that her shocking tell-all was, at least partly, Bentley’s way of staying relevant. As one historian put it, “She knew what was popular, what she could do, and what people would pay to see.”

And in the end, she’d have to grab that fame back with both hands.

Gladys Bentley FactsYou Bet Your Life, NBC

42. She Tried Desperately To Stay Relevant

In many ways, Bentley never stopped trying to be in the spotlight, even as her audiences waned and the world changed around her. On May 15, 1958, she appeared on Groucho Marx’s quiz series You Bet Your Life, where she played piano and sang the jazz classic “Them There Eyes.” Little did anyone know, however, that Bentley didn’t have much time left.

Gladys Bentley FactsYou Bet Your Life, NBC

43. She Was A “Drag King”

When Gladys Bentley performed in speakeasies, especially at the beginning of her career, a curious thing started happening. Places would bill her as a male impersonator or even an actual male performer, thanks to her dapper styling and masculine energy. This “drag king” persona has formed part of her legacy to this day. But it’s more complicated than all that…

Katharine Hepburn FactsShutterstock

44. She Was An Enigma

In truth, Gladys Bentley has been a mystery for decades. Not only did her own time not know what to do with her, but Bentley’s impact is also still a hot topic now. Although Bentley used feminine pronouns in her public life, some experts believe she would have been a transgender man today, while others insist she only played with gender expectations and never tried to “pass” as a man.

Samuel L. Jackson QuizShutterstock

45. She Had A Final Transformation

In the late 1950s, Bentley’s repentance for her star-studded sins took a turn towards God, and she got involved in her local Church and began studying to be a minister. Like everything she did, she did this whole hog, and got ordained at the beginning of the 1960s. It was supposed to be a new chapter in her life, and then tragedy hit.

Stonehenge FactsPikist

46. She Met A Tragic Fate

On January 18, 1960, when Bentley was still just 52 years old, she passed quite suddenly in her Los Angeles home. When word got around that the great Gladys Bentley was no longer with us, her old friends and fans must have been shocked and looking for answers. Yet the reality behind her death was far too simple, and far too tragic.

Mae West FactsShutterstock

47. She Was Gone Too Soon

In the end, the booming, bodacious, and vivacious singer succumbed to the relatively common ailment of pneumonia, which came on quickly and didn’t let her go. In her brief years, Bentley had seen America transform from a hedonistic party to a strait-laced society, and she came out the other side just as changed herself. But she still had one more legacy left.

Wilt Chamberlain factsShutterstock

48. She Made A Huge Revelation

There may be one final bizarre touch to the already strange life of Gladys Bentley. In her Ebony tell-all “I Am A Woman,” Bentley mentions yet another husband, a sailor named Don, who she claims seduced her, turned her straight, and set her on the path to “womanhood” again. The details of this courtship, however, are…shady.

Gladys Bentley FactsAmerican Masters, PBS

49. She Had An Extra Husband

Bentley met Don when he phoned her up one day, claiming to know a mutual friend. Over the course of their acquaintance, Bentley came to realize Don was a “normal” man who was utterly devoted to her, and they eventually started a romantic relationship and even, according to Bentley, married. But there’s something very disturbing about this story.

Rejected Proposals factsWikipedia

50. She May Have Told A Whopper

Though Gladys Bentley notes that her marriage to Don didn’t work out, it still seems like something out of a fairy tale—and perhaps it’s just as untrue as a fairy tale, too. The singer was infamous for making up juicy stories about herself, and this “Don” remains a vague figure in Bentley's life. To her dying day, Gladys Bentley knew how to build a mystery.

Gladys Bentley FactsAmerican Masters, PBS

Sources: 1, 2, 3, 4

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