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Drawing attention to both characters and landscapes, this essay proposes a reading of F. Scott Fitzgerald’s Trimalchio that assesses its differences from and similarities to The Great Gatsby. In the first part of the essay a comparison between the two novels shows that the behavior and features of Jay Gatsby in Trimalchio are borrowed from Petronius’s Trimalchio and Homer’s Odysseus. As a consequence, the first Jay Gatsby turns out to be a more vulgar and astute version of his second and more successful incarnation; he is, nevertheless, a coherent persona. We have ultimately two Gatsbys and, therefore, two different novels. In spite of that, these two texts share the same literary landscape, of which Fitzgerald was evidently sure from the very beginning of his composition process. The second part of the essay focuses on the ways in which Fitzgerald consciously grafted into Gatsby’s American landscape the imperialistic vision exposed in Joseph Conrad’s Heart of Darkness. In this respect, the opposition Fitzgerald—through his narrator Nick Carraway—established between the East and Midwest of the USA also allows for a surprising but compelling connection with David Foster Wallace, an author strongly anchored in his Midwestern point of view.