This chapter offers a a brief survey of Mailer’s ongoing artistic responses and reactions to the postmodern period. Mailer is indebted to his Modernist predecessors but also experiments with perspective and structure in a way that aligns him more closely with definitions of Postmodernism. While this is most evident in his avant-garde films, it is also apparent in the self-referential nature and thematic focus of his nonfiction, as well as in his preoccupation with notions of metamorphosis.