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The hobo is an often overlooked figure that plays a key role in Jack Kerouac’s life and his magnum opus On the Road (1957). The first endeavor of this thesis is presenting the theory that Kerouac’s most prominent influences were hobo authors, rather than those historically claimed by Kerouac, and it appears the hobo had an even greater impact on his writing than Kerouac’s contemporary Beat figures, Neal Cassady, Allen Ginsberg, and William Burroughs. Various biographical details of Kerouac and other Beats intertwine with the political legacy of the hobo and specifically with two works of hobo literature: Woody Guthrie’s Bound for Glory (1943) and Jack Black’s You Can’t Win (1926). Kerouac’s On the Road shares striking similarities with the aforementioned works in both style and theme. The second undertaking is presenting and analyzing John Lennon’s work, Boxcar Politics: The Hobo in U.S. Culture and Literature, 1869-1965 (2014). I utilize Lennon’s Marxist-based theory, “Boxcar Politics,” to demonstrate Jack Kerouac’s hobos are agents capable of political resistance, not simply hopeless ghosts lacking political resistance as Lennon claims in his last chapter of Boxcar Politics where he discusses his take on the hobo’s role in On the Road. Furthermore, I argue that Kerouac’s depictions changed the way Americans retrospectively view the hobo. Once despised by the media and public, the hobo is now a grandfatherly icon of American expansion and adventure. Kerouac’s On the Road greatly contributed to transforming hobos to heroes. Today, the popularity and awards of “proto-Beats” like Bob Dylan exemplify America’s now companionable relationship with the American hobo.