This study focuses on contemporary issues to examine the subjective perceptions of the contemporary individuals regarding the American Dream through postmodern and post-postmodern lenses in American writer David Foster Wallace's books. The selected novels provide divergent portrayals of the American nation culture and individuals. They present the paradoxical experience of postmodernism as their starting point and focus on the Americans' emotional responsiveness to how it feels to live in modern times in America while still trying to pursue their national dream as well. The specific reasons and symptoms burdening the self in the contemporary world are analyzed according to the accounts of postmodern approaches of the period. To re-humanize the subject the self is reconsidered in combination with viewpoints of the recent movement post-postmodernism. The influences of the new era and the American Dream are traced to gain a better insight and manage a deeper investigation. This research takes a closer look at the ideology behind the American Dream and the way it is reflected in contemporary times. The scope of the study covers David Foster Wallace's three novels and situates his stance as an author in postmodern and post-postmodern literature. The nation and its citizens are analyzed from the perspective of Wallace through his three influential novels and his essays will also provide insight to the study.