The publication of the thitherto unavailable original scroll of On the Road in 2007 marked a decisive point for Beat scholarship. Enabling line-by-line comparison, the two versions could suddenly be placed under proper scrutiny, and Kerouac’s revisions set up against the established myth of the novel’s creation. How should we understand the revisions? To supply a contribution to an answer, this paper will map the artistic as well as personal trajectory of Jack Kerouac throughout the 1950s. Basing my analysis largely on correspondence, I will show how Kerouac constantly oscillated between different positions and attitudes within the space of literary production. The essay will argue that Kerouac’s pursuit of literary prestige, stood side by side with the always-present alternative of satisfying the demands of the large audience. If we add to this Kerouac’s obsession with his imagined audience it becomes clear that his final work resulted from more than his own aesthetic preferences. Devoting a section to his aesthetic program, I will explore to what extent editorial revisions, even seemingly minor ones, compromised his original text in significant ways. Keeping in mind his erratic trajectory, and adding to it Warren French’s complementary observation that Kerouac’s personality was violently split, will allow us to identify an equally contradictory literary self-expression. Thus comparing On the Road with Visions of Cody (the latter emerged through the revisions of the former), Kerouac’s literary expression can be said to manifest itself in two fundamentally different ways. In Road as a reifying gesture that mystifies man’s connection with the earth, and, in Visions as an opposite gesture of dereification that seeks to disclose the source of man-made products that have become reified. Proposing that the autobiographical component of Kerouac’s writing is essentially a gesture of dereification, the essay will argue that editorial revisions of such works inescapably destabilize the unity between experienced reality and textual representation.