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A youthful boy screams as his head is forcefully gripped, a large thumb digging into his face as his father's powerful hand holds him by the neck. That moment from The Sacrifice of Isaac visits the Uffizi Gallery, creating unease through the artist's harrowing portrayal of the tormented child from the biblical narrative. It appears as if Abraham, instructed by God to kill his son, could snap his spinal column with a solitary turn. However Abraham's preferred approach involves the metallic steel knife he holds in his other palm, prepared to slit Isaac's throat. A definite element stands out – whomever modeled as the sacrifice for this breathtaking work demonstrated remarkable expressive skill. There exists not just dread, surprise and pleading in his darkened gaze but also deep sorrow that a guardian could betray him so completely.

The artist adopted a familiar biblical tale and transformed it so fresh and visceral that its horrors appeared to unfold right in front of the viewer

Viewing in front of the painting, viewers recognize this as a real countenance, an precise depiction of a adolescent subject, because the same youth – recognizable by his disheveled hair and nearly black eyes – features in several additional paintings by the master. In every case, that highly emotional visage dominates the scene. In Youth With a Ram, he gazes playfully from the shadows while embracing a lamb. In Victorious Cupid, he grins with a hardness learned on the city's alleys, his black feathery appendages demonic, a unclothed child running chaos in a well-to-do residence.

Victorious Cupid, presently exhibited at a British gallery, represents one of the most embarrassing artworks ever created. Viewers feel totally unsettled gazing at it. The god of love, whose darts fill people with often agonizing longing, is shown as a extremely tangible, brightly illuminated nude form, standing over overturned items that include musical devices, a music score, metal armor and an architect's T-square. This heap of possessions echoes, intentionally, the mathematical and architectural gear scattered across the floor in the German master's engraving Melencolia I – except in this case, the melancholic mess is created by this smirking Cupid and the turmoil he can release.

"Love looks not with the vision, but with the mind, / And thus is winged Love depicted sightless," penned Shakespeare, just prior to this painting was produced around 1601. But Caravaggio's Cupid is not unseeing. He gazes straight at the observer. That face – sardonic and rosy-cheeked, looking with brazen assurance as he poses naked – is the identical one that screams in terror in The Sacrifice of Isaac.

When Michelangelo Merisi da Caravaggio painted his three images of the same unusual-looking youth in the Eternal City at the dawn of the seventeenth century, he was the most celebrated religious artist in a metropolis enflamed by religious revival. The Sacrifice of Isaac demonstrates why he was sought to decorate churches: he could take a scriptural story that had been portrayed numerous occasions previously and render it so fresh, so raw and physical that the terror appeared to be happening directly in front of the spectator.

Yet there existed a different side to Caravaggio, evident as soon as he arrived in the capital in the cold season that concluded 1592, as a artist in his initial twenties with no mentor or supporter in the urban center, just skill and boldness. Most of the paintings with which he caught the sacred city's eye were anything but devout. That could be the very first resides in London's art museum. A youth opens his crimson mouth in a yell of agony: while reaching out his dirty digits for a fruit, he has rather been bitten. Boy Bitten By a Lizard is sensuality amid poverty: observers can see the painter's gloomy room mirrored in the murky liquid of the transparent container.

The boy sports a rose-colored flower in his coiffure – a symbol of the erotic trade in early modern art. Northern Italian painters such as Titian and Jacopo Palma depicted prostitutes grasping blooms and, in a painting destroyed in the second world war but documented through photographs, the master represented a renowned female courtesan, clutching a posy to her bosom. The message of all these botanical indicators is clear: intimacy for purchase.

What are we to interpret of the artist's sensual portrayals of youths – and of one boy in specific? It is a question that has divided his interpreters since he achieved widespread recognition in the twentieth century. The complicated past reality is that the artist was neither the homosexual hero that, for example, the filmmaker presented on film in his 1986 movie Caravaggio, nor so entirely devout that, as certain art scholars unbelievably assert, his Youth Holding Fruit is in fact a portrait of Christ.

His initial works indeed make explicit erotic suggestions, or even offers. It's as if Caravaggio, then a penniless young artist, identified with Rome's sex workers, selling himself to survive. In the Uffizi, with this thought in consideration, observers might look to another initial creation, the sixteenth-century masterwork Bacchus, in which the deity of alcohol gazes calmly at you as he starts to undo the black ribbon of his robe.

A few annums following Bacchus, what could have driven Caravaggio to create Amor Vincit Omnia for the art patron Vincenzo Giustiniani, when he was finally growing nearly established with prestigious ecclesiastical commissions? This profane pagan god revives the erotic challenges of his initial paintings but in a more intense, uneasy manner. Half a century afterwards, its secret seemed obvious: it was a portrait of the painter's companion. A English traveller viewed the painting in about the mid-seventeenth century and was told its subject has "the body & face of [Caravaggio's|his] owne youth or assistant that laid with him". The name of this adolescent was Cecco.

The artist had been dead for about 40 years when this account was recorded.