Gladys Bentley was a Harlem Renaissance blues singer and pianist famous not only for her roaring talent and vivacious stage performances but also for embracing her sexuality and living openly, for most of her life, as a lesbian.
Described as weighing 250 pounds wearing elegantly tailored male evening attire complete with bow ties and top hats -her signature piece being a white tuxedo with tails- she went by the stage name Bobbie Minton, she was one the highest paid black women in the US in the 1920’s reportedly raking a weekly salary of $125.00 at one point.
Born in Pennsylvania on August 12, 1907 to a Trinidadian mother and African-American father, she once recalled wearing suits belonging to her younger brothers to school and enduring ridicule for her preference for masculine attire. A serious crush on a female school teacher sent her parents in search of cure taking her various doctors. About growing up she told Ebony Magazine in a 50’s interview“It seems I was born different. At least, I always thought so….From the time I can remember anything, even as I was toddling, I never wanted a man to touch me…Soon I began to feel more comfortable in boys clothes than in dresses”. She left home for New York City at the ripe age of sixteen bound for Harlem- a then mecca for black artists and musicians described as the birthplace of the “New Negro” i.e. blacks taking pride in their race and demanding civil & political rights.
As for her talent she possessed an alto voice and fierce command of the piano and was infamous for creating bawdy parodies for tunes of the day infusing sexually charged content along with bluesy demure. She went
from performing at rent parties graduating to speakeasies and night clubs headlining the likes of The Cotton Club and The Apollo and later hosting her own weekly radio program. She was a staple at famed Harlem speakeasy, Harry Hansberry’s Clam House/The Clam House. By 1934 she was well established with her own musical revue made up of male drag queen dancers.
As for her personal life she once owned a luxurious Park Ave apartment equipped with servants and publicly wed a white female lover in a civil ceremony. With the prohibition of alcohol during the Great Depression and diminishing tolerance Bentley moved to Los Angeles to live with mother, Mary Mote (Bentley). She became a hit in Bay Area gay bars where she cultivated a less bawdy act and local authorities prohibited her from sporting trousers during her show. She recorded music with record label Excelsior in the 1940’s which included songs Find Out What He Likes and Notoriety Papa.
By the 1950’s Bentley cleaned up her act and started donning dresses claiming to have cured her lesbianism now being at peace- possibly due to fear of persecution as openly gay/well known lesbian. She penned an interview for Ebony titled ” I Am A Woman Again” talking about a cure through ingesting female hormones. She claimed to be married to a columnist- J.T Gibson who later denied the union. She later married Charles Robertson, a man sixteen years her junior; the union ended in divorce. Still she performed and appeared twice on Groucho Marx’s television show You Bet Your Life. Though born in Pennsylvania she often said she was from Port of Spain, Trinidad. Bentley died suddenly at age 52 in 1960 from the flu in LA.
Gladys Bentley on “You Bet Your Life”