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São Paulo's nightlife is often considered the most lively in Brazil, and is popularly considered a point of attraction in the city. A major component of this nightlife are the variety of establishments aimed at queer people, especially gay men and trans women. Some of the most popular and highly praised literary portrayals of São Paulo, such as the fictional work of Marcelino Freire and the creative nonfiction of Chico Felitti, focus on queer spaces. These works, however, often juxtapose violence and decadence with a sense of sexual liberation and creativity encountered in this nightlife. I propose that this juxtaposition echoes anxieties that arose during a time when queer Brazilians in the largest cities began to transform their discourse around sexual orientation and gender identity in the 1970s and 1980s. Through an analysis of Freire's Nossos ossos (2013) and Felitti's recent works Ricardo e Vânia (2019) and Rainhas da noite (2023), I will explore the way these new queer identities were breaking away from older Brazilian discourses on gender, sexuality and national identity in the abertura and early democratization period. Nevertheless, I posit that both Freire and Felitti utilize gay and trans characters to tell broader stories about Brazil.