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A youthful boy cries out while his skull is firmly gripped, a massive thumb digging into his cheek as his father's powerful hand grasps him by the throat. This scene from The Sacrifice of Isaac appears in the Uffizi Gallery, evoking unease through the artist's chilling portrayal of the suffering youth from the scriptural narrative. It appears as if Abraham, instructed by the Divine to kill his son, could snap his neck with a solitary turn. However the father's preferred approach involves the silvery steel knife he holds in his remaining palm, ready to cut Isaac's throat. One certain aspect remains – whomever posed as the sacrifice for this breathtaking work displayed extraordinary expressive skill. There exists not just fear, shock and pleading in his darkened gaze but also deep grief that a protector could betray him so completely.

He adopted a well-known biblical tale and made it so vibrant and raw that its horrors seemed to unfold directly in view of the viewer

Standing before the artwork, observers identify this as a actual face, an precise depiction of a adolescent subject, because the identical youth – identifiable by his disheveled hair and almost black eyes – features in several other works by Caravaggio. In each case, that richly emotional face commands the scene. In John the Baptist, he gazes playfully from the darkness while embracing a ram. In Victorious Cupid, he smirks with a hardness acquired on the city's streets, his black plumed appendages sinister, a naked child running chaos in a affluent dwelling.

Amor Vincit Omnia, currently displayed at a British gallery, represents one of the most discomfiting masterpieces ever created. Viewers feel totally disoriented looking at it. The god of love, whose darts inspire people with frequently agonizing desire, is portrayed as a very tangible, brightly illuminated nude form, standing over overturned items that include stringed instruments, a music manuscript, plate armor and an builder's ruler. This heap of items echoes, deliberately, the geometric and architectural gear strewn across the floor in the German master's engraving Melencolia I – save in this case, the gloomy mess is created by this grinning Cupid and the turmoil he can release.

"Love sees not with the vision, but with the soul, / And thus is feathered Love depicted blind," penned the Bard, just prior to this painting was created around 1601. But the painter's Cupid is not unseeing. He stares straight at you. That countenance – ironic and ruddy-cheeked, looking with brazen assurance as he poses unclothed – is the identical one that screams in terror in Abraham's Test.

As Michelangelo Merisi da Caravaggio created his multiple images of the identical distinctive-appearing youth in the Eternal City at the start of the seventeenth century, he was the highly acclaimed religious painter in a city enflamed by religious revival. The Sacrifice of Isaac reveals why he was commissioned to adorn churches: he could adopt a biblical story that had been portrayed numerous times previously and make it so new, so unfiltered and visceral that the horror seemed to be occurring immediately before you.

However there existed another side to the artist, evident as quickly as he arrived in Rome in the winter that ended the sixteenth century, as a painter in his initial 20s with no mentor or patron in the city, only skill and audacity. The majority of the paintings with which he captured the holy city's attention were anything but devout. That could be the very first hangs in London's National Gallery. A youth parts his red lips in a scream of pain: while reaching out his filthy fingers for a fruit, he has instead been attacked. Boy Bitten By a Lizard is eroticism amid squalor: viewers can see the painter's dismal room reflected in the cloudy liquid of the glass vase.

The adolescent sports a rose-colored blossom in his coiffure – a symbol of the erotic trade in Renaissance art. Venetian painters such as Titian and Jacopo Palma depicted courtesans grasping flowers and, in a work destroyed in the WWII but known through images, Caravaggio represented a famous woman courtesan, clutching a posy to her bosom. The message of all these floral signifiers is obvious: sex for purchase.

How are we to interpret of Caravaggio's sensual depictions of youths – and of one adolescent in specific? It is a inquiry that has divided his commentators ever since he achieved mega-fame in the 1980s. The complicated past truth is that the painter was neither the homosexual icon that, for instance, the filmmaker put on screen in his 1986 film about the artist, nor so completely devout that, as some artistic historians unbelievably claim, his Youth Holding Fruit is in fact a portrait of Christ.

His initial works indeed make explicit sexual implications, or even offers. It's as if the painter, then a penniless young artist, aligned with the city's sex workers, selling himself to live. In the Uffizi, with this thought in mind, observers might turn to an additional initial work, the 1596 masterpiece the god of wine, in which the god of alcohol stares coolly at the spectator as he begins to undo the black ribbon of his garment.

A several years following Bacchus, what could have motivated the artist to create Victorious Cupid for the artistic collector Vincenzo Giustiniani, when he was at last becoming almost respectable with prestigious ecclesiastical projects? This unholy pagan deity revives the sexual provocations of his initial paintings but in a increasingly powerful, uneasy way. Fifty years later, its secret seemed obvious: it was a representation of the painter's companion. A English traveller viewed Victorious Cupid in about 1649 and was told its subject has "the physique and countenance of [Caravaggio's|his] owne youth or servant that slept with him". The identity of this boy was Francesco.

The painter had been deceased for about forty years when this account was documented.