Hunter S. Thompson is one of the most culturally pervasive American authors from the late twentieth century, yet there is little academic inquiry into his work. This is especially true for his early work as both an aspiring novelist and a fledgling journalist. This thesis explores his earliest complete work of fiction, The Rum Diary, focusing on the social and historical aspects that contributed to the compositions of the novel. Completed in the early 1960s and published in 1998, The Rum Diary presents an ideal opportunity for analyzing the evolution of Thompson’s entire career as a writer. An exploration of Thompson’s self-mythologization, modernist literary influences, and colonialist ideology lays the groundwork for further analysis of his early output.