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Abstract This dissertation constructs an analytical history of gay theatre in Toronto from 1967 to 1985, a period that saw the radical reformation of the city’s gay community and its not-for-profit theatre industry. It undertakes this research using a cultural materialist theoretical frame that enables it to recover the history of gay theatre in Toronto and connect this history to the contemporary development of gay community and theatrical production in the city. By recovering the history of gay theatre in Toronto, this dissertation demonstrates its seminal importance to the history of gay culture in Canada, and to Canadian theatre history. To construct its narrative of gay theatre history in Toronto, this dissertation focuses on three pioneering gay playwrights, John Herbert, Robert Wallace, and Sky Gilbert, historically contextualizing these within three distinct eras of contemporary gay history and Toronto theatre history. Chapter one addresses the years prior to the decriminalization of homosexuality in Canada in 1969, analyzing the theatrical development of John Herbert’s Fortune and Men’s Eyes, and the political significance of the New York production’s tour to Toronto’s Central Library Theatre in October 1967. Chapter two examines the rise of gay liberation and the Alternative theatre movements, 1969 to 1976, recovering the production history of Robert Wallace’s long-neglected play, No Deposit, No Return. Chapter three investigates the backlash against gay liberation, the consolidation of gay community as a political minority, and the emergence of AIDS, 1977-1985, focusing on the early career of Sky Gilbert, and the significance of his play, Drag Queens on Trial. Paying close attention to the politics of gay identity and community in Toronto, and providing a thick description of the biographical, social, cultural, and political discourses that shaped the lives of these playwrights and impacted the production and reception of their plays, this dissertation reveals the important part gay theatre played in the reformation of Toronto’s gay community and its not-for-profit theatre industry in this foundational period.