This volume offers new insight into the breadth of contexts that inform Norman Mailer’s body of work. It examines important literary, critical, theoretical, cultural, and historical frameworks for Mailer’s writing, highlighting the ways his work reflects the concerns of twentieth and twenty-first century America. This book traces Mailer’s literary influences; his contributions to a variety of literary genres; his participation in the American political sphere; the philosophical, religious, and gendered contexts that shape his work; and the iconic American figures he profiled. The book concludes with reflections on Mailer’s literary and cultural legacy, emphasizing his advocacy for literary freedom and the contemporary resonance of his work.