That was certainly the case at the Clam House, a Prohibition-era speakeasy in Harlem, where Gladys Bentley, one of the boldest performers of her era, held court.
In her top hat and tuxedo, Bentley belted gender-bending original blues numbers and lewd parodies of popular songs, eventually becoming Harlem royalty. When not accompanying herself with a dazzling piano, the mightily built singer often swept through the audience, flirting with women in the crowd and soliciting dirty lyrics from them as she sang.
By the early 1930s, Bentley was Harlem’s most famous lesbian figure — a significant distinction, given that gay, lesbian and gender-defying writers and performers were flourishing during the Harlem Renaissance. For a time, she was among the best-known black entertainers in the United States.
Bentley sang her bawdy, bossy songs in a thunderous voice, dipping down into a froglike growl or curling upward into a wail. In his 1940 autobiography, Langston Hughes called her “an amazing exhibition of musical energy — a large, dark, masculine lady, whose feet pounded the floor while her fingers pounded the keyboard — a perfect piece of African sculpture, animated by her own rhythm.”
In a letter to Countee Cullen, the Harlem socialite Harold Jackman wrote: “When Gladys sings ‘St. James Infirmary,’ it makes you weep your heart out.”
Indeed, Bentley knew her success was built on talent as much as notoriety. “The world has tramped to the doors of the places where I have performed to applaud my piano playing and song styling,” she wrote in a 1952 essay for Ebony. “Even though they knew me as a male impersonator, they still could appreciate my artistry as a performer.”
Bentley’s rise to fame demonstrated how liberated the Prohibition culture of the Harlem Renaissance had become, and how welcoming the blues tradition could be to gay expression. She often confronted male entitlement and sexual abuse in her lyrics, and declared her own sexual independence. This was, in fact, the continuation of a tradition begun by other singers of the early 20th century, particularly Bessie Smith, Ma Rainey and Lucille Bogan, who were some of the most vocal musician critics of patriarchy of their time.
But Bentley was the first prominent performer of her era to embrace a trans identity, implicating her body differently in these acts of musical defiance. (Throughout her life, Bentley used female pronouns to describe herself — at least in public.)
On a 1928 recording of her “Worried Blues,” for OKeh Records, Bentley sang: “What made you men folk treat us women like you do? / I don’t want no man that I got to give my money to.”
Between lines, she improvises vocal fills, uncannily mimicking a trumpet and hitting the notes spot on. On “How Much Can I Stand,” from later that year, she depicted an abusive relationship with a sense of wry humanity:
Women selling snakeskins and alligator tails
Trying to get money to get my man out of jail
How much of that dog can I stand?
Said I was an angel, he was bound to treat me right
Who in the devil ever heard of angels that get beat up every night?
How much of that dog can I stand?
Gladys Bentley was born on Aug. 12, 1907, to Mary Bentley, who was from Trinidad, and George Bentley, an American, and she was raised in Philadelphia. (While most sources list Philadelphia as Bentley’s birthplace, during a rare TV appearance in 1958, she told Groucho Marx that she was originally from Port of Spain, Trinidad.)
The eldest of four siblings, Bentley remembered her childhood as an unhappy one, and from an early age her parents worried about her attraction to women. But she poured her frustrations and self interrogations into music, and her talents as a pianist and songwriter showed themselves quickly. In 1923, at 16, she left home for New York City, where the Harlem Renaissance was already in high gear.
Bentley immediately began performing at house parties and at so-called buffet flats. These were illicit clubs, usually in brownstones, that offered music, alcohol, gambling and often prostitution. But it was at the Clam House — Harlem’s most popular gay-friendly speakeasy, on 133rd Street, nicknamed Swing Street for its countless underground clubs — that Bentley established herself as the main attraction.
Her reputation took off. The house became the talk of Harlem, attracting uptown bigwigs as well as celebrities from all over the city. Bentley’s performances there inspired characters in at least three novels based on Harlem’s night life, including Carl Van Vechten’s voyeuristic “Parties.”
The Clam House appears prominently on the cartoonist Elmer Simms Campbell’s “Night-Club Map of Harlem.” In the center of the image, just off Seventh Avenue, Campbell drew a sketch of Bentley at the piano, writing, “Gladys’ Clam House: Gladys Bentley wears a tuxedo and high hat.”
Bentley recorded intermittently in the ’20s and ’30s, but none of the recordings capture the licentious immersion of her live performances, and she was not widely played on the radio.
Instead, Bentley became a fixture of clubs across the city and eventually toured nationally. At the height of her fame, she said in the Ebony essay, she was living on Park Avenue with a team of servants, paying $300 a month in rent (over $5,000 in today’s dollars) and driving a luxury car. She told reporters that she had married a white woman at a ceremony in New Jersey, though the woman’s identity does not appear to have become public.
In the mid-30s, Bentley was the headliner at the Ubangi Club, running a stage show that featured flamboyantly dressed men dancing in a chorus line behind her. Advertisements for the show stated that she was in charge of a “cast of 30.” She sometimes appeared at the Apollo Theater and the Cotton Club, and held a residency at a club on Park Avenue in Midtown.
During Prohibition, lines blurred between mainstream night life and more illicit forms of entertainment. But over the course of the ’30s, after the 18th Amendment was repealed and the country found itself in the Depression, tolerance waned. Even as Bentley grew more popular, her celebrity became less acceptable — and performing south of Harlem became difficult. In 1934, a run at the King’s Terrace on 52nd Street was cut short under pressure from the police.
In 1937, Bentley left New York for Los Angeles. She became a leading entertainer there and in the Bay Area, though she sometimes had to wear skirts onstage to appease club owners. She was less restricted at Mona’s 440 Club, the first lesbian bar in San Francisco, which became her home base for a time.
The Red Scare brought a new wave of repressive social politics, and McCarthyite attacks on artists placed a particular target on homosexuals. Bentley never stopped touring, but she began to appear consistently in women’s clothing, and in the 1950s she claimed to have gotten married twice to men. (One of them, the journalist J. T. Gibson, denied it.) In 1952, the same year she signed a recording contract with the Swingtime label, she wrote in the Ebony essay (titled “I Am a Woman Again”) that she had undergone hormone treatments to help her identify as heterosexual.
By 1958, she said she had completed an autobiography, “If This Be Sin,” but it was never published. Bentley died in 1960, from complications of the flu, at 52, while studying to become a Christian minister.
For a time, she had been a monarch of the New York night: The simple mention of her name was enough to clue readers in. In October 1936, a New York Times entertainment columnist wrote: “The Ubangi Club, Harlem’s reigning hot spot, will offer a brand new revue tomorrow evening, featuring (of course) Gladys Bentley.”
In another article that month, The Times described the scene she cultivated: “The Ubangi still draws a mixed crowd, is noisy and intimate and gay — altogether Harlem.”