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Cupid; it also calls to mind the many ancient Greek legends about images of art so deceptively convincing that they seemed real – the painted grapes of Xeuxis which, as Pliny the Elder relates, fooled the birds into pecking at them, or the statue of a woman infused with such love by the sculptor Pygmalion that she actually came to life and stepped down off her pedestal. In painting the Sleeping Cupid, Caravaggio was making his own contribution to the imaginary art gallery of the classical past – and living up to the classical compliment that had so recently been paid to him at his investiture as a Knight of Malta. He had been dubbed the new Apelles, and now he was wittily acting the part.

There was yet another layer of allusion for the learned Francesco dell’Antella to enjoy as he contemplated his new possession, this time to a more recent work of art. The subject of Cupid asleep was famously associated with Caravaggio’s namesake, Michelangelo Buonarroti. When Michelangelo was young, he had created a sculpture of a Sleeping Cupid so perfectly classical in spirit that he was able to pass it off as a genuine antique work of art. Giorgio Vasari tells the story:

[He] set himself to make from another piece of marble a Cupid that was sleeping, of the size of life. This, when finished, was shown … to Lorenzo di Pier Francesco [Medici] as a beautiful thing, and he, having pronounced the same judgement, said to Michelangelo: ‘If you were to bury it under ground and then send it to Rome treated in such a manner as to make it look old, I am certain that it would pass for an antique, and you would thus obtain much more for it than by selling it here.’ It is said that Michelangelo handled it in such a manner as to make it appear an antique; nor is there any reason to marvel at that, seeing as he had genius enough to do it, and even more.68

Michelangelo Buonarroti had created a sculpture of Cupid to rival the masterpieces of antiquity. Now Michelangelo Merisi was vying with him by emulating that very act of classical emulation. Implicit in the gesture was the Renaissance conceit of the paragone, a contest between different art forms. Michelangelo, the sculptor, had given tangible form to his Sleeping Cupid. Caravaggio, the painter, could not do that. But he could create a greater illusion of flesh and blood, and he could use his mastery of chiaroscuro to evoke the light of approaching dawn.

The Sleeping Cupid is essentially a jeu d’esprit. But it is also a vitally important painting for the understanding of Caravaggio’s work as a whole, demonstrating his high degree of erudition and establishing beyond any doubt an explicit spirit of competition with Michelangelo, which had seemed at least implicit in so many of his Roman paintings, from The Calling of St Matthew onwards. Francesco dell’Antella made the comparison overtly when he went out of his way to show the picture to a great-nephew of Michelangelo named Francesco Buonarroti, who was also a Knight of Malta; and he then actually sent the work to Florence in the hope that the most celebrated member of the modern Buonarroti family, Fra Francesco’s brother, the poet and dramatist Michelangelo the Younger, would give his opinion of it. Michelangelo the Younger clearly did see this rivalrous homage to his great-uncle’s marble Cupid, because on 24 April 1610, dell’Antella wrote to him to say: ‘I value now more than before my Cupid, after hearing the praise of your Lordship for which I kiss your hand.’69

APELLES IN PRISON

The perennially spiky Caravaggio was celebrated on Malta. In his own estimation he had always been a valent’huomo. Now he was truly being treated like one. Alof de Wignacourt was delighted with the painter’s work for the order. According to Bellori, he was so impressed by the enormous new altarpiece for the Oratory of St John that ‘as a reward, beside the honour of the Cross, the Grand Master put a gold chain around Caravaggio’s neck, and made him a gift of two slaves, along with other signs of esteem and appreciation for his work’.70 Finally, Caravaggio had got