David with the Head of Goliath is a painting by the Italian Baroque artist Caravaggio. It is housed in the Galleria Borghese, Rome. The painting, which was in the collection of Cardinal Scipione Borghese in 1650, has been dated as early as 1605 and as late as 1609–1610, with more recent scholars tending towards the former.

The immediate inspiration for Caravaggio was a work by a follower of Giorgione, c.1510, but Caravaggio captures the drama more effectively by having the head dangling from David's hand and dripping blood, rather than resting on a ledge. The sword in David's hand carries an abbreviated inscription H-AS OS; this has been interpreted as an abbreviation of the Latin phrase humilitas occidit superbiam ("humility kills pride").

It has been said that all artists portray themselves in their work. As over-generalized as this statement may seem, it does seem applicable to David with the Head of Goliath. The face of Goliath bears a striking resemblance to portraits of Caravaggio as an adult.

Regardless of the identities of those portrayed in this intense painting, the emotion with which the painting is charged is still palpable today. The conflict of small vs. massive, the bittersweet victory of winning the fight at the expense of a human life, and the futility of a giant bully against a boy who knows what he must do, is all too evident.

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