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As our modern media landscape has shifted to provide ever-greater access to information and entertainment, so too have individuals become more disconnected from traditional sites of meaning making. David Foster Wallace’s magnum opus Infinite Jest embodies our quintessentially American individualism within the new context of postmodernist fragmentation and information overload. Within Wallace’s tragicomic vision of the future, those shifting foundations engender vicious cycles of solipsistic existence which threaten not only the death of the individual, but the collapse of our American society as a whole.The purpose of this paper is to synthesize critical theories in post-structuralism with studies on entertainment, addiction, and media, in order to better understand the attrition of public faith in institutions in the post-truth era of politics, and to better understand to what extent entertainment itself may act as a countervailing force for that attrition. In the course of this paper, I use Infinite Jest as an inflection point in literature, signaling a shift away from the nihilistic symptoms of the postmodern era in an attempt to reinject meaning, truth, and trust into our society. Going beyond the New Sincerity movement that Wallace called for in a 1993 essay, Infinite Jest signals an attempt by fiction writers at the turn of the millennium to expose the ways our sociopolitical systems are failing to adapt to the social simulacra presented by new media. They warn of postmodernism’s ideology habituating its citizens into solipsistic loops, as this new cultural fabric wraps individuals ever more tightly into isolated existences. Infinite Jest on its own may fall short of providing clear answers as to how to escape the problems generated by this changing media landscape, but nonetheless establishes pivotal preventative and rehabilitative steps to rebuild the foundation of the social sphere.