This study is a multidisciplinary work that draws on fields of literature, cultural studies, philosophy, and politics in order to explore the representation of cultural otherness in three selected contemporary American novels: Plowing the Dark (2000) by Richard Powers, Terrorist (2006) by John Updike, and Point Omega (2010) by Don DeLillo. Using the theory of Orientalism by Edward Said and postmodern thoughts by Jacques Lacan, Slavoj Zizek, and Jean Baudrillard as sub-theories, this book builds a perception on the Western Orientalist and neo-Orientalist representation(s) of the Arab Islamic world. The order of these novels, regardless to their chronology, articulates three Orientalist representations that speak of each author's personal perception of East and West in the context of three different political events: Iran Hostage Crisis (1979), 9/11 terrorist attacks, and the War on Iraq (2003). By situating the three selected novels within the Orientalist discourse, and by exploring their reflections on postmodern American society, the study examines the various strategies of Orientalist (mis)representation as conditioned by American postmodernity.