Gladys Bentley

Birth name: Gladys Alberta Bentley (aka Barbara “Bobbie” Minton)
Birthplace: Philadelphia, Pennsylvania, USA
August 12, 1907 – January 18, 1960
Years Active: 1923 – 1960

In the early 20th century, Blues singer and pianist Gladys Bentley was one of the most popular and successful entertainers in New York City. Bentley regularly performed in a tuxedo with tails and a matching top hat. Her chosen attire was a brave and bold representation of her fluid gender identity and outspoken lesbian sexuality, which she proudly lived both onstage and off. With Louis Armstrong and Duke Ellington, Gladys Bentley was one of the prominent musicians during the Harlem Renaissance (1918-1937).

Born in Philadelphia, Pennsylvania, Bentley’s father was African American and her mother was an immigrant from the Caribbean island of Trinidad. Bentley expressed later in life, “It seems I was born different. At the age of nine, I stole my brother’s suits and began to feel more comfortable in boy’s clothes than in dresses.” Fleeing a home life rife with abuse, including increasing pressure to conform to the societal norms of the gender assigned to her at birth, Bentley moved to New York City in 1923 at the age of sixteen. An exceptional musician, she quickly found work as a pianist, singer, and performer at various clubs in the uptown Manhattan neighborhood of Harlem. Her arrival in Harlem was very well-timed.

With the Harlem Renaissance thriving in the 1920s, Bentley soon became one of the most celebrated (and highest paid) entertainers of the era. African American creativity and culture flourished throughout the district, and within that community, so did a tolerance and celebration of sexual orientation and gender identity – a rarity in American society at the time. Bentley boldly presented a risqué live show that both titillated audiences with her bawdy banter and wowed them with her virtuosic musicality. Simultaneously, she developed a robust career as a recording artist, releasing music on the Okeh, Victor, Excelsior, Swingtime, and Flame record labels. Importantly, while Bentley was a pioneering star attraction in her own right, her valiant expression of personal identity and musical prowess was similar to the experiences of other American music legends of that time, like Blues trailblazers Ma Rainey and Bessie Smith.

Many of the entertainment venues in Harlem during these years were frequented by white patrons who came for both the exceptional performances and the illegal alcohol served during Prohibition. Once Prohibition ended in 1933 (and the attendance of whites at shows dropped off), Black performers, and especially gender nonconforming individuals like Gladys Bentley, received renewed harassment by local law enforcement. Frustrated by the discriminatory practices she was enduring in New York City and recognizing the opportunities to be had in the entertainment industry out west, Bentley moved to Los Angeles in 1937.

For a time, Bentley’s career was reinvigorated in California, both in Los Angeles and San Francisco (where she headlined at the city’s first lesbian bar). However, she faced more difficulties in the 1940s and 1950s. As McCarthyism swept across the nation in the 1950s, Bentley found herself targeted by the prevailing repressive trends throughout society and politics. Although she continued to perform and tour regularly, her live show’s ebullient charm diminished and she noticeably changed the attire she wore both onstage and off to conform to increasingly conservative societal demands. By the late 1950s, she had even taken to publicly discounting her younger lesbian and gender nonconforming self in print and on television. That period is now recognized as possibly the always media savvy Bentley trying to either professionally survive the harsh headwinds she faced in the 1950s or seeking some solace in the safety of heteronormativity, or both.

With an autobiography finished, the search on for a publisher, and having been recently trained as a minister, Bentley unexpectedly died in 1960. An African American musical and cultural legend, and a now-celebrated LGBTQ+ icon, Gladys Bentley helped pioneer a path that has been further paved by numerous Black artists in the decades since her death, including Sylvester and Janelle Monáe.