In 1868 Annie Hindle brought to the American variety theater male impersonation, in which a female character vocalist assumed a realistically male stage persona to sing men’s comic songs about courting women. But Hindle’s gender-transgressive behavior was not limited to the stage: her romantic relationships were primarily with other women, twice disguising herself in male dress to marry. Despite what appears a clear connection between the onset of male impersonation, gender-transgressive dress, and same-sex desire, scholarship on male impersonation has treated a reading of Hindle’s act that engages with the category of sexuality as speculative. Through an examination of Hindle’s repertoire and performance context, this thesis demonstrates that her performance should be read as a form of sexual commentary. Because in the nineteenth-century United States male dress signaled that a woman engaged in same-sex practices, this thesis reads male impersonation as a recognizable representation of unconventional sexual identity.