Through the analysis of modes of representation in three works, Fear and Loathing in Las Vegas (1971) by Hunter S. Thompson, Catch-22 (1961) by Joseph Heller, and The Crying of Lot 49 (1965) by Thomas Pynchon, I will explore the utilization of the non-representational mode in Cold War era literature as encouraged by the pervading paranoia and excess consumerism which marked the cultural landscape of the late 1950s, 60s, and early 70s. In embracing aspects of the counterculture, these authors turned to the non-representational mode, to varying degrees, in an attempt to better convey their own understanding of the cultural reality in which they lived. Therefore, mimesis as the dominant mode of depicting reality was, at least partially, abandoned by these authors as a result of the unique cultural conditions of the Cold War period, and the three enumerated works serve as a focal and grounding point in this discussion due both to their popular appeal and the manner in which they depict the cultural context in question. Further, these shifts in modes of representation, insofar as they are confined to the novelistic structure, help to contextualize the dominant literary shift of the latter half of the 20th century from modernist to postmodernist thinking within these cultural phenomena, thus placing these texts into a dialogue which has often excluded any tracings of similarity through representation.