This work is a historical biography of Gladys Bentley and her blues music. She was a cross-dressing entertainer from the Harlem Renaissance and performed popular songs with added, sometimes improvised sexual innuendo. This study considers the performances of her recorded and written material as trans music, meaning, that black music provided a platform to determine racial, gendered, and sexual cultural expressions changing over time, however, always rooted in black vernacular culture. Using showbills, promotional material, studio recordings and short autobiography, this study follows Bentley’s career as “male impersonator” and the effects lesbian/gay (queer) culture had on her blues. Also, I demonstrate how trans narratives coincide with Bentley’s personal life and how Bentley’s transition to woman offers scholars to consider how narration and historicization archive ‘trans’ in a way that obscures the nuances of queer performance that challenge and resist cisnormative structures and symbols of power. I refer to Black Queer Studies, Black Trans Studies, music history and biography to demonstrate how Black music culture operates as a “trans analytic.” Understanding Black music as a trans music, offers us a historical culture that finds queerness and gender transgression before Gay Liberation made them legible in public and political discourse.