What exactly was Caravaggio's black-winged deity of desire? What secrets that masterwork reveals about the rogue genius

A youthful boy cries out while his skull is firmly gripped, a massive thumb digging into his cheek as his father's powerful palm grasps him by the neck. This scene from The Sacrifice of Isaac appears in the Florentine museum, evoking unease through Caravaggio's harrowing portrayal of the tormented youth from the biblical account. It seems as if Abraham, instructed by the Divine to sacrifice his son, could break his spinal column with a solitary twist. Yet Abraham's preferred method involves the metallic steel knife he holds in his remaining hand, prepared to slit the boy's neck. A certain element stands out – whoever posed as Isaac for this astonishing piece demonstrated remarkable expressive skill. Within exists not just dread, shock and begging in his shadowed eyes but also profound sorrow that a guardian could betray him so completely.

The artist took a familiar scriptural story and made it so vibrant and visceral that its terrors seemed to unfold directly in view of you

Standing before the painting, viewers recognize this as a actual countenance, an accurate depiction of a adolescent subject, because the same youth – recognizable by his tousled hair and almost black pupils – appears in two additional works by Caravaggio. In each case, that richly expressive face dominates the composition. In John the Baptist, he gazes mischievously from the darkness while holding a lamb. In Amor Vincit Omnia, he smirks with a toughness learned on the city's alleys, his black feathery appendages demonic, a unclothed adolescent running riot in a well-to-do dwelling.

Amor Vincit Omnia, currently exhibited at a London gallery, represents one of the most embarrassing artworks ever painted. Viewers feel completely unsettled gazing at it. Cupid, whose darts fill people with frequently painful longing, is portrayed as a very tangible, brightly lit nude form, straddling overturned objects that comprise stringed devices, a musical score, plate armour and an architect's ruler. This pile of possessions resembles, intentionally, the geometric and architectural equipment scattered across the floor in Albrecht Dürer's print Melancholy – save in this case, the gloomy disorder is created by this smirking Cupid and the mayhem he can unleash.

"Love sees not with the vision, but with the mind, / And therefore is feathered Love depicted blind," wrote Shakespeare, just before this painting was created around the early 1600s. But Caravaggio's Cupid is not blind. He stares directly at you. That face – sardonic and ruddy-cheeked, looking with brazen assurance as he poses unclothed – is the same one that shrieks in terror in The Sacrifice of Isaac.

As Michelangelo Merisi da Caravaggio created his multiple images of the identical distinctive-looking youth in Rome at the dawn of the seventeenth century, he was the highly celebrated religious artist in a city ignited by religious renewal. The Sacrifice of Isaac demonstrates why he was commissioned to adorn churches: he could adopt a scriptural story that had been depicted numerous occasions before and make it so new, so raw and visceral that the terror seemed to be occurring directly in front of the spectator.

However there was another aspect to the artist, evident as soon as he arrived in the capital in the cold season that ended the sixteenth century, as a artist in his initial twenties with no teacher or supporter in the urban center, just talent and audacity. Most of the paintings with which he captured the sacred city's eye were everything but holy. That may be the absolute earliest resides in London's art museum. A youth opens his crimson mouth in a scream of agony: while stretching out his dirty fingers for a fruit, he has instead been bitten. Boy Bitten By a Lizard is eroticism amid squalor: observers can discern Caravaggio's dismal chamber mirrored in the cloudy waters of the transparent container.

The boy wears a rose-colored blossom in his coiffure – a emblem of the sex trade in early modern art. Venetian artists such as Titian and Jacopo Palma depicted courtesans holding blooms and, in a painting destroyed in the second world war but known through photographs, Caravaggio portrayed a renowned female prostitute, clutching a bouquet to her bosom. The meaning of all these botanical indicators is obvious: intimacy for sale.

How are we to interpret of Caravaggio's erotic depictions of youths – and of a particular adolescent in particular? It is a question that has split his commentators since he achieved mega-fame in the twentieth century. The complicated historical reality is that the artist was not the queer hero that, for instance, Derek Jarman put on screen in his twentieth-century movie Caravaggio, nor so entirely pious that, as some art scholars unbelievably claim, his Boy With a Basket of Fruit is in fact a portrait of Jesus.

His initial works do make overt erotic implications, or even propositions. It's as if the painter, then a penniless young creator, aligned with the city's sex workers, offering himself to live. In the Uffizi, with this idea in consideration, viewers might look to another early creation, the 1596 masterwork the god of wine, in which the god of alcohol gazes coolly at the spectator as he starts to untie the dark sash of his garment.

A several years following Bacchus, what could have driven the artist to create Amor Vincit Omnia for the artistic collector the nobleman, when he was at last growing almost respectable with important church projects? This profane non-Christian god resurrects the sexual provocations of his early works but in a increasingly powerful, unsettling manner. Fifty years afterwards, its hidden meaning seemed obvious: it was a portrait of Caravaggio's lover. A British traveller saw Victorious Cupid in about 1649 and was told its subject has "the physique and countenance of [Caravaggio's|his] owne boy or servant that slept with him". The identity of this boy was Francesco.

The artist had been dead for about forty annums when this account was recorded.

Ellen Byrd
Ellen Byrd

Tech enthusiast and digital strategist with a passion for exploring emerging technologies and their impact on society.