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In the Old Testament story, Judith seduces and deceives Holofernes, eventually cutting off his head. Despite the many versions produced throughout history, the biblical story - and the outcome - essentially remain the same. Holofernes always loses his head. This, however, is not the case in the realm of art. Pictorial representations of the Book of Judith can be found as early as the eighth century in Europe, steadily increasing throughout the Middle Ages and booming in the Early Renaissance. Amongst these Renaissance adaptations are images of Judith planning the beheading, raising her sword in the instant before, stowing away the head immediately after, and returning home with the aftermath. But never the decapitation itself. That is, until the year 1599 and the emergence of Caravaggio. Unlike the many artists before him, the early Baroque master decisively places the dramatic climax of the story at the immediate center of his canvas, and in a form which is so radically realistic and shockingly brutal that it carries no true predecessors in the entire history of art. This text pursues a deeper understanding of the artistic anomaly which is Caravaggio's Judith Beheading Holofernes.