Postcard featuring Bentley's famous white tuxedo and top hat, circa 1937

Gladys Bentley Was The Gender Nonconforming, Lesbian Superstar Of The Harlem Renaissance

by BUST Magazine

Harlem Renaissance superstar Gladys Bentley brought infamy to her favorite venue—a notorious speakeasy called the Clam House—and created a gay nightlife scene 100 years ahead of its time.

Dressed in a tailored white tuxedo and backed up by a chorus line of female impersonators, singer/pianist Gladys Bentley was outrageous—even at a time when Harlem was legendary for its nightlife. A 1936 article in The Afro American described her stage act this way: “Prancing about in her cream-colored full dress suit, her hair closely chopped and slicked down into a pompadour, Miss Bentley (whom many mistake for a man) delivers her prize number ‘Nothing Now Perplexes Like the Sexes, Because When You See Them Switch, You Can’t Tell Which is Which.’” She was, the article hardly needed to add—but did—“one of the most notorious entertainers in all of Manhattan.”

Bentley’s notoriety followed her offstage, as well. A photo from 1931 shows the 24-year-old dressed in a shirt, tie, and suit jacket, with a fedora worn at a jaunty angle. She is wearing a skirt, but even so, this was daring street wear for a woman. Still more daring was the fact that she didn’t care to hide that she was a lesbian. One night in the early 1930s, she sidled up to Broadway columnist Louis Sobol and whispered in his ear: “I’m getting married and you’re invited.” When Sobol asked the identity of the lucky man, Bentley giggled. “Man? Why boy you’re crazy. I’m marryin’…,” and named another female singer.

Gladys Bentley was born in Philadelphia in 1907, the oldest of four children in a poor family. According to an article she wrote for Ebony in 1952, she always knew she was “different.” She loved wearing her brothers’ suits—a fondness that got her sent home from school on more than one occasion. Her size also set her apart. As an adult, the newspapers called her “bulky,” “ungainly,” and worse (“that ton of hot licorice”) as they praised her act; she even briefly recorded under the name “Fatso Bentley.”

Bentley in her black top hat and tuxBentley in her black top hat and tux

She felt older than her elementary school classmates, too. While they were at recess, Bentley stayed in with their teacher, cleaning erasers and performing other small chores. Sometimes the teacher let the girl comb what Bentley later remembered as “her long, beautiful hair.” During the day, Bentley wondered why she was so attracted to her teacher. At night, she dreamed of her. “I didn’t understand the meaning of those dreams,” she wrote in Ebony in 1952, “until later.” Perhaps her dawning awareness, along with the fact that her family had begun to drag her from doctor to doctor seeking a cure for her difference, are among the reasons Bentley left home at age 16. She headed straight to Harlem.

This was an excellent choice for a musically talented, gender nonconforming teenager in 1923. Harlem was becoming the center of African-American life in Manhattan just around the time of Bentley’s birth, when black realtors took advantage of an economic depression to buy apartment houses north of Central Park and offer them to black tenants. Harlem’s African-American population increased with the Great Migration of Southern blacks to Northern states, lured by industrial jobs vacated by whites mobilized for the First World War, as well as by a desire to escape Jim Crow. By the time Bentley arrived, the Harlem Renaissance was in full swing, with the area the center of African American political, religious, and cultural life in New York, and beyond. “They called themselves ‘New Negroes,’ Harlem was their capital, and they manifested a new militancy and pride,” wrote Bentley’s biographer, Eric Garber.

There was, however, another side to Prohibition-era Harlem. Whites flocked to the neighborhood to “engage in vices which they would not attempt in their own communities,” wrote a columnist for the Amsterdam News. Under the lenient administration of Mayor Jimmy Walker, the police looked away from speakeasy action even though the sale of alcohol was illegal under the Volstead Act. (A signature Harlem drink was a pink mixture of gin and wine called a “Top and Bottom.”) Marijuana was plentiful. And while homosexuality remained against the law, drag balls drew thousands of spectators, gay and straight, while bordello-like apartments called “buffet flats” offered the adventuresome all kinds of sexual experiences. Meanwhile, Harlem’s music scene was hopping. The Cotton Club is well remembered (run by the mob, it maintained a strict whites-only entrance policy), but there were dozens of other clubs: The Mad House, The Exclusive Club, The Plantation, The Yeah Man, Connie’s Inn, and Pod’s, to name but a few.

“A Night-Club Map of Harlem” shows speakeasy venues of 1932, including “Gladys’ Clam House”

Bentley played at rent parties (a house party where a hat is passed to help pay the rent) and at many of the aforementioned small clubs after her initial arrival in Harlem. She was playing for tips at Connie’s Inn one night when a friend told her that The Mad House was desperately looking for a replacement pianist. “But they want a boy,” her friend said. “There’s no better time for them to start using a girl,” Bentley replied. What Bentley described in Ebony as a “terrific burst of applause” after her first number at The Mad House convinced the manager she was right, and she was hired on the spot.

The Mad House gig paid the rent, but Harry Hansberry’s Clam House is the place where Bentley found fame. The Clam House was a narrow room holding only eight tables, located on the strip of West 133rd Street between Seventh Avenue and Lenox known as “Jungle Alley.” This moniker, along with that of The Ubangi Club, where Bentley regularly performed in the mid-1930s, are graphic indicators of how white visitors and those who sought to make money off of them viewed Harlem and its residents as primitive, exotic “others.” While race relations mostly remained calm, poet and Bentley fan Langston Hughes recalled in his 1940 memoir that, “Non-theatrical, non-intellectual Harlem was an unwilling victim of its own vogue. It didn’t like to be stared at by white folks.”

She was playing for tips at Connie’s Inn when a friend told her that The Mad House was looking for a pianist. “But they want a boy,” her friend said. “There’s no better time for them to start using a girl,” Bentley replied.

Photographer, novelist, and all-around scenemaker Carl Van Vechten was one of the white intellectuals who helped publicize Harlem as a destination for socialites looking for kicks. A friend and patron to Langston Hughes and other black artists and writers, Van Vechten was mesmerized by Gladys Bentley’s drag king persona almost as much as her musical talent. He quickly became a super fan, seeing her perform either at the Clam House or private parties (at least one in his own home) nearly 20 times in 1929 and 1930. He even gave Bentley her first white tuxedo, a look that became her trademark.

Postcard featuring Bentley's famous white tuxedo and top hat, circa 1937Postcard featuring Bentley’s famous white tuxedo and top hat, circa 1937

Van Vechten’s enthusiasm helped bring Bentley to the attention of white nightclub goers, but the show she put on was what made them come back and bring their friends. Dressed at first in what she later described as “immaculate white full-dress shirts with stiff collars, small bow ties [and] short Eton jackets,” her bobbed hair “slicked straight back,” Bentley accompanied herself on the piano as she sang parodies of popular songs that ranged from risqué to obscene. Consider, for example, her parody of “My Alice Blue Gown.” As sung in the Broadway musical Irene (1919), the original lyrics went like this:

“And the world seemed to smile all around
‘Til it wilted, I wore it,
I’ll always adore it
My sweet little Alice blue gown.”

Bentley’s parody was anything but sweet:

“And he said, ‘Dearie, please turn around’
And he shoved that big thing up my brown
He tore it. I bored it. Lord, how I adored it
My sweet little Alice blue gown.”

A straight and mournful version of “St. James Infirmary Blues” was also on her set list, but it was Bentley’s naughty lyrics and pounding piano that put  her on the map—literally: a 1932 “Night-Club Map of Harlem” renamed her preferred venue “Gladys’ Clam House.”

Bentley looking over a scrapbook of her career, circa 1952Bentley looking over a scrapbook of her career, circa 1952

The songs Bentley recorded for the Okeh record label in 1928 capture none of her bawdy appeal. They are straightforward blues, filled with tales of domestic abuse, poverty, and sorrow, leavened by Bentley’s piano and excellent vocal impression of a trumpet. “Washboard Get Together,” a 1930 recording with the Washboard Serenaders, is a wordless, up-tempo number that shows off Bentley’s superb scatting. However, it’s a recording from much later in her career that provides the best example of her teasing wordplay. “Boogie’n My Woogie” is a Bentley original recorded by the Gladys Bentley Quintette in 1945. Bentley pounds out a fantastic boogie beat, and joyously sings:

“There was a hip old lady who lived in a shoe
She had no children
She knew what to do!”

The singer describes the kind of man she likes, but then comes a gender-bending verse:

“I was in the army
now the war is through
look out pretty mama
I’m coming home to you.”

By 1930, Bentley was a bona fide star. Her name appeared almost daily in the show business gossip columns of both white and black newspapers across the United States. She had her own 15-minute radio show on KPCH in Hoboken, NJ. A fictionalized version of Bentley even made it into a pair of novels. Carl Van Vechten worked a reference to a “girl up there” in Harlem with hair “like a wet seal and when she pounds the piano the dawn comes up like thunder” into his comic 1930 novel, Parties. And Blair Niles’ 1931 novel, Strange Brother, included among its cast of characters, a large black piano player named Sybil, who entertains a racially mixed audience of gays and straights at a tiny nightspot called The Lobster Pot.

Bentley sporting her signature closely-cropped hair, box-tie, and pricey tuxedoBentley sporting her signature closely-cropped hair, box-tie, and pricey tuxedo

Celebrities also crowded into the dark, smoky Clam House to hear “La Bentley” (the columnist who so dubbed her then wondered if the pronoun should be masculine). Among them was actress Tallulah Bankhead, another salty dame with a fondness for women, who visited in 1931. Too many puzzle pieces are missing to know if there was a connection—and if there was, who influenced whom—but the following year, Marlene Dietrich showed up as a nightclub singer in a white tuxedo, tickling the chin of a female admirer, in the film Blonde Venus.

She had a line of six chorus boys behind her—sometimes dressed as sailors, sometimes as women. She sang specially written material with “conscious vulgarity….”

Bentley’s fame eventually became too large for the Clam House. She moved on to bigger and fancier nightclubs (or went “plumb hinkety” as one columnist described it), but her act wasn’t quite the same. She still dressed in a top hat and tails, and sang her dirty ditties, while sliding “in and out among the tables, teasing here, and provoking there.” But now she had an accompanist and a line of six chorus boys behind her—sometimes dressed as sailors, sometimes as women. She sang specially written material with “conscious vulgarity…. The old magic of the woman and the piano and the night and the rhythm being one is gone,” wrote Langston Hughes.

Bentley herself, on the other hand, recalled her transition to the clubs of Midtown Manhattan fondly. “I appeared in tailor-made clothes, top hat and tails, with a cane to match each costume,” she wrote in Ebony. “Two black outfits, one maroon, and a tan, grey, and white…. I was an immediate success.” She made strides in her personal life as well, departing her St. Nicolas Avenue apartment in Harlem to live among what one black newspaper referred to as “the ofay [a derogatory term for whites] socially prominent” in a swanky $300-a-month (about $5500 in 2016 dollars) apartment on Park Avenue, with servants and “a beautiful car.”

Not everyone was a fan. Vere E. Johns, a columnist at The New York Age, perhaps reacting to the “conscious vulgarity” on display, panned Bentley’s revue in 1934, and denigrated her sexuality along the way. The troupe “gave first class portrayals of sex perversion, as their form of entertainment, and I have it on the printed word of the Amsterdam News that theirs was no play-acting, but the real things.”

Indeed, Bentley could be seen “marching down Seventh Avenue attired in men’s clothes” any day of the week, recalled writer Wilbur Young, and appeared to thrive on the tongue-wagging “her odd habits” elicited. The “Man About Harlem” columnist at The New York Age (seemingly less uptight than Vere E. Johns) made note in 1936 of “the buxom Gladys Bentley entering the Alhambra [Theater] late Saturday afternoon while three chicks stood amazed.” And to top it all off, there was her rumored wedding to a white woman in a New Jersey civil ceremony.

Bentley and bandleader Willie Bryant, 1936Bentley and bandleader Willie Bryant, 1936

The repeal of Prohibition in 1933 darkened many of the speakeasies, while a 1935 Harlem riot scared off many whites from traveling uptown when they could legally drink closer to home anyway. The Clam House was “just another cellar” by 1938. Around the same time, a crackdown on risqué acts “also wrecked the drawing power of Gladys Bentley of Harlem, who preferred to wear male clothes and sing off-color songs,” according to columnist Ralph Matthews in The Afro-American.

This was a nonissue, because by that time, Bentley had moved to Los Angeles to be closer to her mother. Throughout the 1940s, she did club dates up and down California (including at Mona’s 440 Club, a legendary lesbian bar in San Francisco) as well as in Chicago and back in New York.

Then something odd happened. First came rumors in a 1949 issue of The Pittsburgh Courier that the formerly out and proud Bentley had “been confined to an institution after her recent marriage” to an unnamed man. Three years later, the same paper reported the confounding news that she had done “a complete switch from her top hat and tails personality to dresses and wigs for a feminine front.” The August 1952 issue of Ebony magazine then carried a shocking confession straight from Harlem’s foremost “bulldagger.” “I Am a Woman Again” was Gladys Bentley’s story of how “the miracle” of hormone treatments had helped her overcome “her strange affliction” and led to her happy marriage to “a well-known West Coast theatrical columnist.” In the article, Bentley recounted her career with pride, though her descriptions of her large salary, Park Avenue apartment, and servants were at odds with photos of her in what looks like a maid’s uniform, making dinner and turning back the bed covers “to make homecoming husband comfortable.”

Was this, as several historians suggest, a ploy to shield what remained of her career at a time when McCarthyism made public homosexuality more dangerous than ever? Was it because Bentley was becoming more religious? At the time of her much-too-early death in 1960 from pneumonia at age 52, she was waiting to be ordained as a minister in the Temple of Love In Christ, Inc.

Bentley, illustrator Prentiss Taylor, and singer Nora HoltBentley, illustrator Prentiss Taylor, and singer Nora Holt

No matter her intentions, her attempt at hetero-conformity seems to have met with limited success. The man she named as her “husband” later denied in print they were ever married. A 1957 Chicago Defender article on “The Third Sex” included Bentley in its salacious discussion of lesbianism, dredging up the ancient history that she used to wear men’s clothes, as well as the accusation that she had acted as “the husband to a number of women, both colored and white,” the latter detail adding a dash of racial horror. Bentley, the article went on, tried to change her ways by marrying a man, yet when a visiting friend asked about a pair of pictures on her dresser, Bentley replied: “That’s my husband (pointing to the male) and that’s my wife.”

In Bentley’s only filmed performance, a 1959 appearance on Groucho Marx’s game show, You Bet Your Life, she is dressed as a woman. She seems somewhat nervous and claims to be from Port-of-Spain, Trinidad (her mother’s birthplace). But her charisma shines through the moment she sits down at the piano to offer a smoking hot version of “Them There Eyes.” Those nights at The Clam House must have been something else, indeed.

You can hear all of Bentley’s recorded output, as well as view photos, ephemera, and her 1959 appearance on You Bet Your Life, on JD Doyle’s fantastic site,


Written by Lynn Peril


This article originally appeared in the October/November 2016 print edition of BUST Magazine. Subscribe today!

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