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Cross-Dressing Blues Artist Gladys Bentley Was ‘Out’ Ahead of Her Time

In 1934, New York City’s King’s Terrace nightclub faced closure after complaints about its “dirty songs.” The venue had been hosting a troupe led by Gladys Bentley, an audacious piano-playing blues artist who thrilled and scandalized audiences with her provocative music.

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Gladys Bentley. Wikipedia photo.
Gladys Bentley. Wikipedia photo.

By Tamara Shiloh

In 1934, New York City’s King’s Terrace nightclub faced closure after complaints about its “dirty songs.” The venue had been hosting a troupe led by Gladys Bentley, an audacious piano-playing blues artist who thrilled and scandalized audiences with her provocative music.

Born in Phila., Pa., Bentley arrived in Harlem around 1925 at the age of 16 and became part of the vibrant artistic community during the influential Harlem Renaissance. Proudly embracing her identity as an African American woman who loved other women, donned men’s clothing, and sang risqué songs, Bentley challenged societal norms.

Although Bentley’s performances prevented her from gaining mainstream recognition and limited her inclusion in history books, her portraits now grace the African American History Museum’s music collections.

Starting her career in Harlem’s rent party circuit, Bentley wowed audiences with her deep, growling voice and scatting skills. She fearlessly added explicit lyrics to popular tunes, leaving a lasting impact on her listeners.

While her popularity soared in the rent party scene, Bentley also pursued opportunities in established Harlem nightclubs. At the Mad House on 133rd Street, she convinced the skeptical boss to give her a chance.

Bentley’s energetic piano-playing and unique style of fashion, featuring immaculate dress shirts, bow ties, oxfords, and short Eton jackets, set her apart as a “male impersonator.” Her flirtatious interactions with women in the audience captivated all who witnessed her performances.

As Bentley’s career flourished, she graced prominent Harlem venues such as the Cotton Club and the Clam House, a renowned gay speakeasy. Her act attracted diverse audiences, including both African Americans and white patrons. Writers like Carl van Vechten were drawn to Bentley’s talent, featuring her as a character in their works.

In the 1930s, she headlined at Harlem’s Ubangi house, where she was backed by a chorus line of drag queens.

With the repeal of Prohibition, the club scene in Harlem declined. She relocated to Southern California, where she was billed as “America’s Greatest Sepia Piano Player” and the “Brown Bomber of Sophisticated Songs” according to Wikipedia. She continued performing in upscale venues but in a more subdued manner than her earlier days in Harlem. Harassed for wearing men’s clothing, she began facing scrutiny during the repressive McCarthy era in the 1950s.

In a 1952 article for Ebony magazine titled “I Am a Woman Again,” Bentley shared her life story. She recounted her glamorous life as a performer and her personal struggles existing in a realm between traditional gender boundaries. Bentley claimed to have undergone medical treatment that awakened her “womanliness” and mentioned her marriages. However, the veracity of these claims remains uncertain.

Bentley continued her career for a few more years but succumbed to pneumonia in 1960. Today, her story is being rediscovered and celebrated as that of a gender outlaw and a pioneer of self-expression.

Bentley’s defiance of societal norms serves as a reminder of the power of self-expression, resilience, and the courage to challenge expectations. Her legacy inspires individuals to embrace their true selves fearlessly.

Bentley’s contributions to the Harlem Renaissance and her unyielding embrace of her identity remain impactful. Her audacity and refusal to conform continue to inspire generations. Gladys Bentley, an extraordinary performer, trailblazer, and symbol of empowerment, leaves a lasting impression on those who follow her path.

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