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This article interprets Poe’s tales of perversity as Hegelian critiques of the antebellum culture of sentiment. Whereas progressive author-activists like Emerson and Stowe honored the benign impulses of the moral sentiment theorized by eighteenth-century philosophers, Poe, in such tales as The Narrative of Arthur Gordon Pym, “The Black Cat,” and “The Imp of the Perverse,” ventriloquized this discourse of “sensus communis” to insist instead upon the malignity of the so-called “sixth sense.” Replacing Adam Smith’s sympathetic “man within the breast” with Descartes’s “evil genius,” Poe held that the man within the breast is an agonistic “Arch-Fiend,” a demonic “imp” who prompts us to do violence to both self and other. Thus, although Poe was in many respects sympathetic to contemporaneous sentimental critiques of reason—critiques that challenged Kant’s association of morality with reason alone—he also sought to complicate their frequently monological understanding of affective morality. In so doing, Poe not only articulated a conservative skepticism regarding the putatively benign nature of humans; he also posited that liberal subjectivity is, paradoxically, self-annihilating—a point that renders the “imp of the perverse” a poetical correlative of the Hegelian process of “tarrying with the negative,” one illustrative of the cunning of unreason.