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Over an active career of more than fifty years, Alessandro Magnasco developed a highly original painterly manner which, when combined with picaresque subject matter adapted from Spanish literature, presented viewers with images of literary pícaros in many guises (beggars, gypsies, soldiers, and monks), social and religious deviants cast in fictitious landscapes and interiors. I am not the first to propose that Magnasco's paintings share thematic and iconographic affinities with the picaresque literary genre, but this study is the first to confront the conceptual and methodological consequences of proposing such intertextual relationships. From the beginning, this study has sought to expand upon other scholars' limited interpretations of Magnasco's "picaresque" oeuvre. To date, these interpretations have lacked the textual endorsement of primary source materials (the original content of the novels and novellas), and none has made use of the conceptual resources available through contemporary literary scholarship, in which genre typologies, reception theories, and notions of fictitiousness have all been gainfully applied to picaresque texts. This study mitigates these deficits, expanding the operative definition of a picaresque text to include pictorial representations of comparable content, to the end of justifying other scholars' habits of calling Magnasco's paintings "picaresque." I have tested the relataionship of a number of works—by Magnasco and his forebears—to the most paradigmatic picaresque novels: including the anonymous texts "Lazarillo de Tormes" and "Estebanillo González," Alemán's "Guzmán de Alfarache," Quevedo's "La vida del buscón," Cervantes's "Novelas ejemplares," and Lesage's "Gil Blas de Santillane." This study explores the painter's use of genre conventions like stock characters (the beggar boy, lazy soldier, inquisitor, galley slave, disenfranchised nobleman), typological settings (the roadside tavern, bandits' lair, inquisitorial prison, gypsy encampment), and thematic schemas (hunger, servitude, imprisonment, self-aggrandizement through costume and deportment), such that viewers may consider the paintings as dialogically related to the novels. I conclude that audiences might thus perceive the images as representing pictorial fictions analogous to the literary fictions created and conventionalized by the picaresque author.