David with the Head of Goliath

Emerging from a wall of shadow, a young David stands holding the head of the fallen giant Goliath. Caravaggio painted this scene around 1610, in the final stretch of a life full of trouble and turmoil. The Italian master was famous for chiaroscuro, a bold play of light and dark, and it shines through here. David's bare shoulder and the folds of his white cloth catch the light and seem to float, while everything behind him dissolves into black.

The real twist lies in Goliath's face. Many experts think Caravaggio painted his own features onto the severed head. At the time he was a wanted man, having killed someone in a brawl, and he sent this painting to Rome in the hope of winning a pardon. Instead of triumph, David wears an expression closer to pity, gazing at his defeated enemy with something like sorrow. Coming from an artist who knew guilt and remorse all too well, the mood feels less like a hero's victory and more like a confession painted in oil.