This essay investigates the evolving portrayal of the biblical heroine Judith in early Baroque Italy through an interdisciplinary analysis that foregrounds the dialogue between dramatic literature and visual art. It traces the transformation of Judith’s character from an emblem of unambiguous virtue to a figure marked by the paradoxes of piety, beauty, and violent agency. Focusing on select theatrical works by Alberti, Salvadori, and Della Valle, alongside paintings by Caravaggio, Artemisia Gentileschi, Cristofano Allori, and Fede Galizia, the study demonstrates how these parallel artistic traditions engaged in a reciprocal exchange of themes and imagery. By exploring this interplay, the essay reveals how representations of Judith both reflected and influenced contemporary cultural attitudes toward female power, seduction, and heroism within the context of religious and societal conventions. Particular attention is given to the role of patronage and the expectations of intended audiences in shaping these interpretations. Ultimately, the essay argues that the Baroque period constructed Judith as a deeply ambivalent figure, emblematic of the era’s simultaneous fascination with and anxiety about female agency.