This project explores the roles and representation of angst in three of Jack Kerouac's novels: On the Road, Tristessa, and Big Sur. These novels especially lend themselves to an analysis of the angst perpetuated by modernity in mid twentieth-century America. The works have a narrator in common, albeit referred to by different names in each, representative of the author (Kerouac) himself. The projection of anxiety due to various ailments in relation to post-war America are specifically concentrated on in this analysis. The identification and dealing with this arrangement comprise the subject of this thesis. A generation of disconnected youth describes the majority of the cohort in post-World War II America. The novels of Jack Kerouac, in particular On the Road and other works in The Duluoz Legend (Kerouac's cannon), project the experiences of the Beat Generation; who, embody more than any other, the notion of disenfranchisement. The thriving dominant middle class made Kerouac and the Beats uneasy with their attitude toward institutionalized employment, the pursuit of money, consumerism, and the repressed conformist values implemented in the name of morality. Jack Kerouac encapsulated best, the mode of energetic unease that motivated the behavior of the dominant (White males) in the mid twentieth-century. Kerouac's writing is ultimately about the search for meaning and identity in an ostensibly fuming and meaningless environment. It is through The Duluoz Legend, specifically On the Road, Tristessa, and Big Sur, that Kerouac is able to testify to the angst felt by the lost generation of the late 1940's and 1950's. Despite Kerouac's inability to accept society on its own terms, his revelations still attract the curious and excluded. Kerouac's mid-century malaise illustrates his characterization of the sensitive, impressionable, and angst ridden disposition that continues to accompany the reality today; that, the American dream is no longer tenable, and in fact, disparaging.