Summary Gladys Bentley (1907-1960) the eldest of four in a Trinidadian immigrant family, left Philadelphia, Pennsylvania at age 16 to join New York's Harlem Renaissance jazz scene. She became an instant sensation after performing at the most popular gay speakeasy, the Clam House, and soon headlined shows and toured the country as a pianist and singer. In a time when homosexuality was widely considered sinful and deviant, Bentley wore men's clothing -- a tuxedo and top hat -- and became famous for her lesbian-themed lyrics covering popular tunes of the day, and for openly flirting with women in the audience. At the height of her popularity, Bentley staged highly produced jazz cabaret performances at the Ubangi Club, where she was joined on stage by a chorus line of female impersonators. But a convergence of circumstances -- the anti-gay sentiments of the time period, numerous states enacting legislation outlawing gender cross-dressing, and the scrutiny and disapproval of the African American church -- had a chilling effect on Bentley's career. In the 1950s, succumbing to "Lavender Scare" pressure from the McCarthy Era harassment of the LGBTQ+ community, Bentley said of her gender identity, "I am a woman again!" and started performing in women's clothing. She died of complications from a flu virus while studying to become an ordained minister. Interviewees: Cookie Woolner, Assistant Professor of History, University of Memphis and author of The Famous Lady Lovers; Dwandalyn Reece, Curator of Music and Performing Arts at the Smithsonian Institution's National Museum of African American History and Culture; Shirlette Ammons, award-winning poet and musician, and songwriter of debut album, "Twilight for Gladys Bentley."

• Documentary
• Biography
• History