In this paper, I examine the life of Billy Tipton, a jazz musician who lived most of his life in Spokane, Washington, as a prominent entertainer and pianist. He is significant because he was a transgender performer who never underwent gender reassignment surgery and passed successfully throughout his adult life, with his assigned gender only being revealed upon his death. He lives largely in the public eye as an inspirational early trans performer, with perhaps the most notable tributes being the opera “Billy” based on his life and staged in Olympia, Washington (performed only three times), a jazz musical, ''The Slow Drag,'' which was performed Off Broadway and the Billy Tipton Memorial Saxophone Quartet, a feminist all-woman saxophone quartet based in Seattle.