Leading with the Chin focuses on the Esquire writings of James Baldwin, Truman Capote, Raymond Carver, Don DeLillo, Norman Mailer, and Tim O'Brien to examine how these authors negotiated important shifts in American masculinity. Using the works of these six authors as case studies, Leading with the Chin argues that Esquire permitted writers to confront national fantasies of American masculinity as they were impacted by the rise of neoliberalism, civil rights and gay rights, and the cultural dominance of the professional-managerial class. Applying the methodologies of periodical studies and the theoretical concerns of masculinity studies, this book recontextualizes the prose and fiction of these authors by analyzing them in the material context of the magazine. Relating each author's articulation of masculinity to the advertisements, editorials, and articles published in each issue, Leading with the Chin shows that Esquire reflected and helped to shape the forces that structured American masculinity in the twentieth century.