Both Jack Kerouac and Ernest Hemingway were once regarded as spokespersons for their generations. One was a member of the Beat Generation, while the other was associated with the “Lost Generation.” This thesis is a comparative analysis of four texts; two by Kerouac and two by Hemingway. The primary texts are as follows: On the Road, Satori in Paris, The Sun Also Rises, and A Moveable Feast. The first three have been defined as romans a clef, while the last is a memoir. In terms of composition, it is clear that all of these texts have their geneses in biography. One of the main focuses of this thesis is the problematic relationship between fact and fiction. How do we distinguish autobiographical writing from fiction when narratives, such as the roman a clef, are derived from actual experiences in the author’s life? As constructs, the “Beat Generation” and the “Lost Generation” both seem to be founded upon what critics have termed “the dialectics of the sacred and the profane.” In relation to this concept, Myth is also an important subject in this thesis. Besides myth, this thesis also discusses mythopoeia, i.e. myth-making, in terms of how the authors construct their personas through narrative writing. Critics have often spoken of thematic similarities between The Sun Also Rises and On the Road; this thesis is also an investigation of the thematic similarities and dissimilarities between the two writers.