This essay explores how the Cold War conflict between the U.S. and the Soviet Union led to a tremendous reorganization of how Americans thought about identity, especially queer identity. The author discusses the activism of homosexual organizers who worked against state repression and then traces the shifting ways Cold War-era novels, plays, and poetry take up the subject of queerness and re-imagine the social possibilities for the homosexual citizen. The work of Tennessee Williams, Patricia Highsmith, and James Baldwin portrays same-sex desire as a social problem and records an overwhelming anxiety about the characters who are aligned with such desires. Later texts by writers such as Audre Lorde and Cherríe Moraga situate same-sex desire as a means of radical critique and as a site of connection. They make legible the active repression of gender and sexual nonconformity. This essay illustrates how ideas of queer freedom arise and transform in the shadow of repression.