The Picture of Dorian Gray is rightly famous for its haunting plot about a work of art that betrays the intimate secrets of both artist and model. But the motif of the magically revealing portrait predates Wilde and comprises several important narrative functions and themes in nineteenth-century fiction before the fin-de-siècle. This essay revisits Wilde’s novel by way of exploring a frequently overlooked connection: the motif of the uncannily revealing portrait was, in fact, a recurrent, if not a regular, feature of earlier nineteenth-century American literature, including key works by Nathaniel Hawthorne, Edgar Allan Poe, and Henry James. The critical tendency to emphasize the contexts of English aestheticism and French decadence—and the influence of Pater and Huysmans, in particular—has yielded a keen appreciation of The Picture of Dorian Gray’s relation to the history of sexuality; indeed, its pivotal role in that history is a now-familiar comprehension of the novel. But the American sources examined here—in particular, Hawthorne’s “The Prophetic Pictures” (1837), Poe’s “The Oval Portrait” (1842), and James’s “The Story of a Masterpiece” (1868) and “The Liar” (1888)—highlight the formal complexities of Wilde’s work, as well as thematic concerns. At least part of the novel’s lasting genius, this chapter contends, lies in its transatlantic genealogy: Wilde learned from his American predecessors how to work within and against a censorship-prone and puritanical dominant culture—and to do so by a canny use of uncanny generic devices.