This dissertation offers the term “negative masculinity” as an analytic for a variety of ways of thinking about freedom in postwar American literature. This term is built in part by theories of freedom in American political thinking that value individualism and autonomy, and this dissertation connects core aesthetics of American subjectivity to the role of masculinity in a variety of literary narratives. In doing so, this dissertation offers a way to critically analyze postwar American narratives’ relationship between freedom and masculinity, and it argues for the ways in which forms of dissent can be legitimized against the totalizing force of hegemonic white masculinity. Its first chapter focuses on the ways in which individuality and community intersect with how freedom is imagined by way of Ken Kesey’s One Flew Over the Cuckoo’s Nest and John Okada’s No-No Boy. In the second chapter, James Baldwin’s Another Country and Colson Whitehead’s John Henry Days are placed in contrast to consider the historical differences that produce Baldwin’s pessimism and Whitehead’s utopianism in consideration of the role of negative masculinity for different histories of black masculinity. The third chapter considers how the evolving nature of American military conflict problematizes the war narrative, and it looks to contemporary American literature written by veterans of the wars in Iraq and Afghanistan for the ways in which they attempt to place their narratives within and outside of the history of American war literature. Lastly, this dissertation’s fourth chapter considers the modern, regressive form of masculinity in contemporary alt-right movements, and it uses Bret Easton Ellis’s American Psycho to understand the disconnect between reality and fantasy in the performance of mastery. Each of these chapters are read with this analytic of negative masculinity in mind, and the term proposed here offers a way to reconsider the relationship between freedom, masculinity, and subjectivity throughout the literary narratives of postwar American literature.