In classical music there has been an effort in recent years to bring to light those whose artistic output contributed to their genre or era but were not as well-memorialized as their caucasian heteronormative male counterparts. So, what about artist-musicians, and those adjacent to them, who lived outside the gender constructs of their contemporary hegemony? What contributions did they purposefully or inadvertently make? What is their reception history and how were these histories documented? Queer Studies in- and outside of musicology has made strides to recognize the existence of historic queer and gender nonconforming individuals. Generally speaking, the aim has been to legitimize the gender spectrum and to make the lives of these noteworthy individuals known. Still it’s impossible for us to know how these gender non-conformists would have categorized their own gender in the Early Modern and Modern Periods were they to have the same terminology as we have today. In this thesis I will cite figures from plays and broadsheet ballads of the 17th century, the developing opera genre in France in the early 18th century, the “low style” in London society and theater in the early 19th century, through to the Reconstructionist United States. By illuminating queer and gender nonconforming individuals and the performative acts that defined their personal lives, I show that these communities have always existed in some iteration and in many facets of the musical universe. What emerges is a centuries-old artistic lineage between gender non-conforming people that has yet to be fully explored.