The massive cultural and social changes brought about by World War II and its aftermath enabled what came to be known as the “sexual revolution.” This chapter highlights some key novels and literary movements that responded to and helped shape the postwar discourse of sexual freedom. It attends first to battles over literary censorship in the first half of the 1960s, focusing on celebrated obscenity trials of the work of Henry Miller and William Burroughs. The chapter then turns to novelistic engagements with queer liberation, discussing the work of James Baldwin, Edmund White, Rita Mae Brown, and Leslie Feinberg, among others. Using these literary examples, it demonstrates how tensions between individualism and collectivism that are longstanding in the American political project play out in and are transformed by ideas of sexual liberation.