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This paper examines the relationship between widowhood and political agency in Canto 37 of Orlando furioso. Ariosto famously begins the canto by singling out Vittoria Colonna as the ideal widow, praising her poetic immortalization of her husband as so exemplary that she surpasses even the classical paragon Artemisia, who drank her husband’s ashes and built him a magnificent funeral monument. I consider this praise in conjunction with the fictional widow Drusilla, whose tale of betrayal at the hands of the tyrant Marganorre’s son, and her bloody reprisal, takes up the rest of this canto concerned with wifely devotion and widowly vengeance. I posit Drusilla as herself a composite of several exemplars, both widowed and not—Camma, Dido, Judith, Lucretia—whose drastic actions contributed to civic and societal change, and discuss the ensuant implications for both Marganorre’s fictional kingdom, and, more importantly, Colonna’s own political and poetic identity.