The late nineteenth century saw the publication of the first medical texts in western Europe that defined a condition known as inversion—a concept that set the precedent for modern categories such as homosexual and transgender. However, prior to their official medicalization, ideas about race, sex, and sexuality that informed twentieth-century identity constructions were already circulating in mass culture and musical entertainment. This dissertation investigates musical, sonic, and performative means through which gendered and sexual difference were articulated in nineteenth-century U.S.-American culture. I argue that musical and theatrical performance are not merely sites where identities are represented; rather, performance plays a key role in the formation and maintenance of those identities. Chapter 1 deals with staged impersonation—encompassing racial and ethnic impersonation, as well as female and male impersonation in which both actors and characters are white. By contextualizing impersonation within a) a broader cultural zeitgeist of illusion, hoaxing, and curiosity, b) contemporary racial ideologies, and c) contemporary journalism about cross-dressing people off the stage, I argue that this genre instructed audiences to understand cross-dressing, passing, or otherwise gender nonconforming people to be impersonating something they were not. Chapter 2 examines a repertoire of popular songs that depict Oscar Wilde and the aesthetic movement. Through practice-based musical performance and analysis of physical gestures, I argue that these songs articulated ideas about Wilde’s sexual otherness that could not be expressed in print. Chapter 3 looks at the writings and musicking of an individual, Ralph Werther-Jennie June, who identified h/imself as an androgyne, or fairie. I explore musical and performative means through which Werther-June articulates h/is experience of sexual difference, and also navigates through states of extreme abjection. I conclude with a discussion of Todd Haynes’ 1998 film, Velvet Goldmine, which demonstrates the persisting centrality of performative tropes and techniques such as innuendo, camp, and impersonation to queer expression, representation, and reception in U.S.-American culture—and displays the tendency of prevailing queer narratives to be about both white people and imposture, despite those narratives being built upon racialized rubrics, and cultural work done by people of color.