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A youthful boy cries out while his skull is firmly gripped, a massive digit pressing into his cheek as his father's mighty palm grasps him by the throat. That moment from The Sacrifice of Isaac appears in the Uffizi Gallery, evoking distress through Caravaggio's chilling rendition of the suffering youth from the scriptural account. The painting appears as if Abraham, commanded by the Divine to sacrifice his son, could snap his spinal column with a single turn. However the father's preferred method involves the metallic grey knife he grips in his other palm, prepared to cut the boy's neck. A definite element remains – whomever modeled as Isaac for this astonishing piece demonstrated remarkable acting skill. There exists not just fear, shock and pleading in his shadowed gaze but additionally deep sorrow that a protector could abandon him so utterly.

The artist took a well-known biblical tale and made it so vibrant and raw that its terrors seemed to unfold right in view of the viewer

Viewing before the painting, viewers identify this as a real face, an precise depiction of a young subject, because the same youth – identifiable by his tousled hair and nearly dark pupils – features in two other works by Caravaggio. In each case, that highly expressive face commands the scene. In John the Baptist, he peers playfully from the darkness while embracing a lamb. In Victorious Cupid, he smirks with a toughness acquired on the city's alleys, his black plumed appendages demonic, a naked adolescent creating chaos in a affluent dwelling.

Amor Vincit Omnia, currently displayed at a London museum, constitutes one of the most discomfiting artworks ever created. Viewers feel totally disoriented looking at it. Cupid, whose darts inspire people with frequently agonizing longing, is portrayed as a very tangible, brightly illuminated unclothed form, straddling toppled-over objects that comprise stringed instruments, a musical manuscript, plate armour and an builder's ruler. This heap of possessions resembles, intentionally, the geometric and construction equipment scattered across the floor in the German master's engraving Melancholy – except here, the gloomy disorder is caused by this grinning Cupid and the mayhem he can unleash.

"Love looks not with the vision, but with the soul, / And thus is feathered Love painted sightless," wrote the Bard, just prior to this work was produced around 1601. But the painter's god is not blind. He stares straight at you. That face – sardonic and ruddy-faced, looking with bold confidence as he struts naked – is the same one that shrieks in terror in The Sacrifice of Isaac.

As the Italian master painted his multiple portrayals of the identical unusual-appearing kid in Rome at the dawn of the seventeenth century, he was the highly acclaimed religious painter in a metropolis enflamed by Catholic revival. Abraham's Offering reveals why he was commissioned to adorn sanctuaries: he could take a biblical story that had been depicted many times before and render it so fresh, so raw and visceral that the horror seemed to be occurring immediately before the spectator.

However there was another side to Caravaggio, evident as soon as he came in Rome in the cold season that ended the sixteenth century, as a artist in his early twenties with no mentor or patron in the urban center, only talent and boldness. The majority of the works with which he caught the sacred city's attention were anything but holy. That may be the very first resides in London's National Gallery. A young man parts his crimson lips in a yell of pain: while reaching out his dirty digits for a cherry, he has rather been attacked. Boy Bitten By a Lizard is sensuality amid squalor: viewers can discern the painter's gloomy chamber reflected in the cloudy waters of the glass container.

The boy sports a pink flower in his coiffure – a emblem of the sex trade in Renaissance art. Northern Italian artists such as Titian and Palma Vecchio portrayed courtesans holding flowers and, in a painting lost in the WWII but known through images, Caravaggio portrayed a renowned woman courtesan, clutching a bouquet to her bosom. The message of all these floral signifiers is clear: sex for purchase.

What are we to make of Caravaggio's erotic portrayals of youths – and of a particular adolescent in particular? It is a inquiry that has split his commentators since he achieved mega-fame in the twentieth century. The complicated historical truth is that the artist was neither the queer hero that, for instance, the filmmaker put on screen in his 1986 movie about the artist, nor so completely devout that, as certain art historians improbably claim, his Boy With a Basket of Fruit is actually a likeness of Jesus.

His early works do offer overt erotic suggestions, or even offers. It's as if Caravaggio, then a penniless youthful artist, aligned with the city's sex workers, selling himself to survive. In the Florentine gallery, with this thought in consideration, viewers might look 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 starts to untie the dark sash of his garment.

A several years after Bacchus, what could have motivated the artist to create Amor Vincit Omnia for the artistic patron the nobleman, when he was at last becoming nearly respectable with important ecclesiastical commissions? This profane pagan god resurrects the sexual challenges of his initial paintings but in a increasingly powerful, uneasy manner. Fifty years later, its hidden meaning seemed obvious: 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 youth or assistant that laid with him". The name of this adolescent was Cecco.

The painter had been deceased for about 40 annums when this account was documented.