early age, Bentley defied gender normative behaviors and femininity. She was larger in size and preferred to wear her brother's suits instead of dresses or blouses. As a result of her lack of gender conformity, she was teased by her classmates and often ostracized by her family and peers. Bentley recalled dreaming and being infatuated with her primary school female teachers but did not understand those feelings until later on in her life. Bentley's behavior was seen as abnormal and "unladylike" which led to her family sending her to doctors to fix Bentley's desires. Later psychiatrists would coin Bentley's non-heteronormative behavior as "extreme social maladjustment." Due to her inability to feel conformable and her family's inability to accept her as she was, Bentley ran away from home at the age of 16 to begin her life in New York City. Career She moved from Philadelphia to Harlem, a neighborhood in New York City in 1925 at the age of 16. She heard that Harry Hansberry's Clam House on 133rd Street, one of the city's most notorious gay speakeasies, needed a male pianist. This is when she began performing in men's attire ("white full dress shirts, stiff collars, small bow ties, oxfords, short Eton jackets, and hair cut straight back"), and here she perfected her act and became popular and successful. Her salary started at $35 per week plus tips and went to $125 per week, and the club was soon renamed Barbara's Exclusive Club, after her stage name at the time, Barbara "Bobbie" Minton. She then began performing at the Ubangi Club on Park Avenue, got an accompanist on piano, and was successful enough to own a "$300/month apartment in Park Ave. With servants and a nice car" (although some have said that she was living in the penthouse of one of her lesbian lovers). She toured the country, some destinations being Cleveland, Pittsburgh, Chicago, and Hollywood, where she was well liked by Cesar Romero, Hugh Herbert, Cary Grant, Barbara Stanwyck, and other celebrities. Bentley had great talent as a piano player, singer, and entertainer. Her performances were "comical, sweet and risqué" for the era and the audience. In her music, she called out men and openly sang about sexual relationships which was seen as risqué behavior at the time. Even more, she often sang about "sissies" and "bulldaggers" and, through innuendo or more literally, about her female lovers, and