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This essay explores the connection between architectural tropes and sexual rhetoric in Melville’s short story “I and My Chimney.” The argument focuses on the inversion of conventional hierarchies such as top/bottom, straight/crooked, masculine/feminine, and natural/depraved. These inversions are all centered on the massive chimney of the story, guiding the rhetorical redistribution of unspoken queer desire through inverted parallels and a preoccupation with all things “backwards.” The trope of verticality combines with Melville’s use of different back-turning syntactical devices, such as periodic sentences and hypotaxis, to disrupt the forward motion of the plot. An analysis of rhetorical schemes such as polyptoton further reveals how Melville’s linguistic confusions disrupt the sexual hierarchy of phallus and anus to an extent that compels us to reconsider the phallo-centrism that Melville critics have argued is more or less universal to his style. The “backwardness” of Melville’s rhetoric expresses an inexpressible desire that can only be represented by a prose style turned against itself, which mimics the narrator’s resistance towards normative living arrangements of the mid-nineteenth century.