Sleeping Cupid is an oil painting by Michelangelo Merisi da Caravaggio, from 1608. The work was started and completed in Malta and commissioned by Francesco Dell’Antella, Grand Knight of the Order of Malta. The theme of a sleeping cupid, holding an arrow in his hand and the bow set aside, represents the abandonment of worldly pleasures – and it is possible that Dell’Antella has ordered it as if to show the fulfilment of his vow of chastity. Against a dark background – a distinctive mark of the painter – a warm and intense beam of light shows the cupid lying naked and asleep, under a sharp contrast of light and shadow. An extreme realism reveals a mark on the character’s face, probably caused by a childhood illness, which Caravaggio might have portrayed from the observation of a sick child.