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F. Scott Fitzgerald’s “The Cruise of the Rolling Junk” remains a critically neglected text. This article proposes that one reason for this neglect is that the work has yet to be placed into any greater critical context. It remedies this problem by analyzing the essay in the context of the American road narrative. Specifically, the reading places Fitzgerald’s work within its own historical moment by recognizing how it both distances itself from and yet is complicit in the romantic idea of travel as expressed by the twentieth-century travel orator Burton Holmes. Through a close reading of the text, the article argues that while Fitzgerald attempts to break from the overly picturesque view of travel and adventure that colored much early travel and road literature in an effort to highlight the sense of identity loss (in terms of self and world), he is, in the end, unsuccessful in fully accomplishing his own narrative goal. However, in his attempt, Fitzgerald does place himself within the greater conversation of the American road narrative and helps to complicate traditional theories of American road literature.