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This paper explores the artistic dialogue between Belgian painter James Ensor and American writer Edgar Allan Poe, focusing on how Ensor's illustrations reinterpret Poe's stories through a lens of social, political, and religious critique. Rather than emphasizing Poe's horror or detective elements, Ensor gravitates toward tales that reflect his own preoccupations: human folly, religious hypocrisy, death, and conformity. Through detailed analysis of Ensor's visual responses to «The Tell-Tale Heart», «The Black Cat», and «The Devil in the Belfry», the study reveals how Ensor's art «guides the fancy» by exposing undercurrents of martyrdom, duplicity, and public gullibility. Ensor's work does not merely illustrate Poe's texts but transforms them into complex, layered commentaries on 19th-century anxieties, aligning with Poe's own aesthetic principles of suggestiveness and complexity.