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

The young lad cries out while his head is forcefully gripped, a massive digit digging into his cheek as his parent's mighty palm grasps him by the throat. This moment from Abraham's Sacrifice appears in the Florentine museum, evoking unease through the artist's harrowing rendition of the tormented youth from the scriptural narrative. The painting seems as if the patriarch, commanded by the Divine to kill his offspring, could snap his neck with a solitary twist. Yet the father's preferred method involves the silvery grey blade he grips in his other hand, prepared to cut the boy's neck. One certain aspect stands out – whomever posed as the sacrifice for this astonishing piece demonstrated remarkable acting skill. Within exists not only dread, surprise and begging in his shadowed eyes but also profound grief that a guardian could abandon him so completely.

The artist adopted a familiar biblical tale and made it so fresh and raw that its horrors seemed to unfold right in view of you

Standing before the painting, viewers recognize this as a real face, an accurate record of a young subject, because the identical youth – identifiable by his tousled locks and almost black pupils – appears in several additional works by Caravaggio. In each instance, that richly expressive face dominates the composition. In John the Baptist, he peers playfully from the darkness while holding a lamb. In Amor Vincit Omnia, he grins with a hardness learned on the city's streets, his dark plumed appendages sinister, a unclothed adolescent creating riot in a well-to-do residence.

Victorious Cupid, currently displayed at a British gallery, represents one of the most discomfiting masterpieces ever created. Observers feel completely disoriented looking at it. The god of love, whose darts fill people with frequently agonizing desire, is portrayed as a extremely real, brightly lit nude figure, standing over toppled-over items that include musical instruments, a musical score, metal armour and an architect's ruler. This pile of items resembles, deliberately, the geometric and construction equipment strewn across the floor in Albrecht Dürer's engraving Melancholy – except in this case, the gloomy disorder is caused by this grinning deity and the mayhem he can unleash.

"Love sees not with the eyes, but with the soul, / And thus is winged Love painted sightless," penned the Bard, just before this painting was created around 1601. But the painter's Cupid is not blind. He stares straight at you. That countenance – sardonic and ruddy-faced, looking with brazen confidence as he struts unclothed – is the same one that screams in terror in Abraham's Test.

When Michelangelo Merisi da Caravaggio painted his multiple portrayals of the same unusual-looking kid in the Eternal City at the start of the 17th century, he was the highly celebrated sacred painter in a city enflamed by religious renewal. Abraham's Offering demonstrates why he was commissioned to decorate sanctuaries: he could adopt a scriptural story that had been depicted numerous occasions previously and make it so new, so unfiltered and visceral that the terror seemed to be occurring directly in front of the spectator.

However there was a different aspect to Caravaggio, apparent as quickly as he arrived in Rome in the cold season that ended 1592, as a painter in his early twenties with no teacher or patron in the city, just skill and audacity. Most of the paintings with which he caught the holy metropolis's attention were anything but holy. What could be the very earliest hangs in the UK's art museum. A youth opens his crimson mouth in a scream of agony: while reaching out his filthy fingers for a cherry, he has rather been attacked. Boy Bitten By a Lizard is eroticism amid squalor: viewers can discern the painter's dismal chamber mirrored in the cloudy waters of the transparent container.

The boy wears a rose-colored flower in his hair – a symbol of the erotic commerce in Renaissance painting. Venetian artists such as Titian and Jacopo Palma portrayed courtesans holding flowers and, in a work lost in the second world war but documented through photographs, the master represented a famous woman courtesan, holding a bouquet to her bosom. The message of all these floral signifiers is clear: intimacy for sale.

What are we to make of the artist's sensual depictions of youths – and of one adolescent in specific? It is a question that has divided his interpreters since he gained mega-fame in the 1980s. The complicated historical truth is that the artist was neither the homosexual hero that, for example, Derek Jarman put on screen in his twentieth-century film Caravaggio, nor so entirely devout that, as certain artistic historians unbelievably assert, his Boy With a Basket of Fruit is in fact a portrait of Jesus.

His early paintings do make explicit sexual suggestions, or including propositions. It's as if the painter, then a penniless young creator, aligned with the city's prostitutes, selling himself to survive. In the Uffizi, with this idea in mind, observers might turn to another initial creation, the 1596 masterpiece the god of wine, in which the god of wine stares coolly at the spectator as he starts to undo the dark ribbon of his garment.

A several years after the wine deity, what could have motivated Caravaggio to paint Amor Vincit Omnia for the artistic collector Vincenzo Giustiniani, when he was at last growing almost established with important ecclesiastical commissions? This profane pagan deity revives the erotic provocations of his initial paintings but in a increasingly intense, uneasy manner. Fifty years later, its secret seemed clear: it was a portrait of Caravaggio's companion. A British traveller viewed the painting in about 1649 and was informed its figure has "the body & face of [Caravaggio's|his] own youth or servant that laid with him". The identity of this adolescent was Cecco.

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

Jennifer Boyd
Jennifer Boyd

A seasoned entrepreneur and digital strategist with over a decade of experience in scaling tech startups and mentoring founders.