Who exactly was the black-winged god of desire? What insights that masterpiece reveals about the rebellious genius

The youthful lad cries out as his skull is firmly gripped, a massive thumb digging into his face as his parent's powerful palm grasps him by the neck. That moment from The Sacrifice of Isaac visits the Uffizi Gallery, evoking distress through the artist's chilling portrayal of the suffering youth from the biblical account. It appears as if Abraham, instructed by the Divine to kill his offspring, could snap his neck with a solitary twist. However Abraham's chosen approach involves the silvery grey blade he grips in his remaining hand, ready to cut the boy's throat. One certain element stands out – whoever modeled as Isaac for this breathtaking piece displayed remarkable expressive skill. There exists not only fear, shock and pleading in his darkened gaze but additionally deep grief that a protector could betray him so completely.

He adopted a familiar scriptural story and made it so fresh and visceral that its terrors appeared to happen right in front of the viewer

Viewing before the painting, observers identify this as a real countenance, an precise record of a young subject, because the same youth – identifiable by his tousled locks and nearly black eyes – features in two additional paintings by the master. In each case, that richly expressive face commands the composition. In John the Baptist, he gazes mischievously from the shadows while embracing a ram. In Victorious Cupid, he grins with a toughness learned on the city's streets, his dark plumed wings demonic, a naked adolescent running riot in a well-to-do residence.

Victorious Cupid, presently displayed at a British museum, constitutes one of the most embarrassing artworks ever painted. Observers feel totally unsettled looking at it. Cupid, whose darts fill people with often agonizing longing, is shown as a very tangible, vividly illuminated unclothed figure, straddling overturned objects that include musical devices, a musical manuscript, metal armour and an architect's T-square. This pile of items resembles, intentionally, the geometric and architectural gear scattered across the ground in Albrecht Dürer's print Melancholy – save in this case, the melancholic disorder is caused by this grinning Cupid and the mayhem he can unleash.

"Love looks not with the eyes, but with the soul, / And therefore is feathered Love painted sightless," wrote the Bard, just prior to this work was created around 1601. But Caravaggio's Cupid is not blind. He stares straight at the observer. That countenance – sardonic and rosy-faced, looking with brazen assurance as he poses naked – is the identical one that screams in fear in The Sacrifice of Isaac.

As the Italian master painted his multiple portrayals of the same distinctive-looking kid in Rome at the start of the seventeenth century, he was the most acclaimed sacred artist in a city ignited by Catholic renewal. The Sacrifice of Isaac demonstrates why he was commissioned to decorate churches: he could adopt a biblical story that had been portrayed many times before and make it so new, so raw and physical that the horror appeared to be occurring directly in front of the spectator.

Yet there existed a different side to Caravaggio, apparent as soon as he arrived in the capital in the winter that concluded 1592, as a artist in his initial twenties with no teacher or supporter in the urban center, just talent and audacity. The majority of the works with which he captured the sacred metropolis's attention were anything but devout. That may be the absolute earliest resides in London's National Gallery. A youth parts his crimson lips in a scream of pain: while stretching out his dirty digits for a cherry, he has rather been bitten. Boy Bitten By a Lizard is sensuality amid squalor: viewers can see the painter's dismal room reflected in the cloudy liquid of the glass vase.

The adolescent wears a pink flower in his coiffure – a emblem of the sex commerce in early modern painting. Venetian painters such as Tiziano and Jacopo Palma depicted courtesans holding blooms and, in a painting lost in the WWII but known through photographs, Caravaggio portrayed a renowned woman courtesan, clutching a posy to her chest. The meaning of all these botanical signifiers is clear: sex for sale.

How are we to make of the artist's sensual portrayals of boys – and of one boy in specific? It is a inquiry that has split his interpreters since he gained widespread recognition in the twentieth century. The complicated historical reality is that the artist was neither the homosexual icon that, for instance, Derek Jarman presented on screen in his 1986 film about the artist, nor so entirely pious that, as some artistic historians unbelievably assert, his Youth Holding Fruit is actually a likeness of Jesus.

His initial paintings do make explicit erotic suggestions, or even offers. It's as if Caravaggio, then a penniless young artist, aligned with the city's sex workers, selling himself to survive. In the Florentine gallery, with this idea in mind, viewers might look to an additional early creation, the 1596 masterpiece the god of wine, in which the deity of alcohol gazes coolly at the spectator as he starts to undo the black sash of his robe.

A few years following the wine deity, what could have motivated the artist to create Amor Vincit Omnia for the artistic collector the nobleman, when he was at last becoming almost established with important church commissions? This unholy non-Christian god revives the erotic challenges of his initial paintings but in a more powerful, uneasy manner. Fifty years afterwards, its hidden meaning seemed clear: it was a representation of Caravaggio's companion. A British traveller saw Victorious Cupid in about 1649 and was informed its figure has "the body & face of [Caravaggio's|his] own boy or assistant that slept with him". The identity of this boy was Cecco.

The painter had been dead for about forty annums when this story was documented.

Margaret Wong
Margaret Wong

A thoughtful writer and life enthusiast passionate about sharing authentic stories and inspiring others through personal growth.