The progression of culture and literature in the three subsequent eras of Modernism, Postmodernism and Post Postmodernism since the late-20th-century can be considered as one of the vivid factors that has led to the chain of transformation of man. In Modernism, the superiority of authentic and governmental power over people was dominant and later in the era of Postmodernism or the late capitalism, the notion of fragmentation controlled the life of the people,but in the third one, Post Postmodernism, a freshgenus of humanism was introduced by innovative authors such as David Foster Wallace who, in his philosophy of writing, illustrates not only the pain and limitations of man but also the healing instruments. Philosophically speaking, through the critical gates of Wallace’, s philosophy, the subjectivity of man is given a niche, and thanks to the opportunity he has gained in the social networks, he could have made it possible to create a type of sharing and mutual communication amongst the fragmented individuals. That is to say, all alienated and limited individuals can have the role of active agents, communicators, and producers instead of being passive watchers, readers, and one-way communicators organized by the structures of the past eras. Therefore, the present study aims to investigate David Foster Wallace’, s (1962-2008) trilogy—, The Broom of the System (1987), Infinite Jest (1996), and The Pale King (2011)—, according to his philosophy of Post postmodernism.