The postmodern movement is best understood as a literary and artistic progression that arose from the ashes of modernism sometime in the twentieth century. It appears that this movement has undergone yet another transformation in recent years, with writer David Foster Wallace and director David Lynch at the forefront of this advancement. In order to better understand the innovative qualities found within the works of these auteurs, I must first examine the elements that shaped the modern movement, as well as the cultural shifts in the late 1950s and early 1960s that led to the emergence of postmodernism. By looking closely at postmodernism's roots, through the lens of Jean-Franc_ois Lyotard, Fredric Jameson, and John Barth, we can better grasp this movement's cultural and artistic significance. The heart of my thesis lies within the examination of three non-fiction journalistic writings by Wallace: "A Supposedly Fun Thing I'll Never Do Again," "David Lynch Keeps His Head," and "Host." I hope to demonstrate how these specific essays violate traditional textual boundaries in order to say something new about contemporary culture. I will also examine Lynch's most recent film, Inland Empire, which strays from the conventional boundaries of Hollywood filmmaking in order to present an unorthodox cinematic perspective. By looking closely at these particular texts, I seek to gain a better understanding in how Wallace and Lynch have found new, perhaps even post-postmodern voices to describe the disillusionment, anxiety, and fear felt within post-9/11 American society. What can readers and viewers take away from such creations? This is the primary focus of my research, as well as to explore where postmodernism can go next -- if indeed there is anywhere left to go.