Caravaggio left Cesari, determined to make his own way after a heated argument. At this point he forged some extremely important friendships, with the painter Prospero Orsi, the architect Onorio Longhi, and the sixteen-year-old Sicilian artist Mario Minniti. Orsi, established in the profession, introduced him to influential collectors; Longhi, more balefully, introduced him to the world of Roman street-brawls. Minniti served Caravaggio as a model and, years later, would be instrumental in helping him to obtain important commissions in Sicily. Ostensibly, the first archival reference to Caravaggio in a contemporary document from Rome is the listing of his name, with that of Prospero Orsi as his partner, as an ‘assistante’ in a procession in October 1594 in honour of St. Luke. The earliest informative account of his life in the city is a court transcript dated 11 July 1597, when Caravaggio and Prospero Orsi were witnesses to a crime near San Luigi de’ Francesi.

An early published notice on Caravaggio, dating from 1604 and describing his lifestyle three years previously recounts that “after a fortnight’s work he will swagger about for a month or two with a sword at his side and a servant following him, from one ball-court to the next, ever ready to engage in a fight or an argument, so that it is most awkward to get along with him.” In 1606 he killed a young man in a brawl, possibly unintentionally, and fled from Rome with a death sentence hanging over him. The Fortune Teller, his first composition with more than one figure, shows a boy, likely Minniti, having his palm read by a gypsy girl, who is stealthily removing his ring as she strokes his hand.

The theme was quite new for Rome, and proved immensely influential over the next century and beyond. This, however, was in the future: at the time, Caravaggio sold it for practically nothing. The Cardsharps—showing another naïve youth of privilege falling the victim of card cheats—is even more psychologically complex, and perhaps Caravaggio’s first true masterpiece. Like The Fortune Teller, it was immensely popular, and over 50 copies survive. More importantly, it attracted the patronage of Cardinal Francesco Maria del Monte, one of the leading connoisseurs in Rome. For Del Monte and his wealthy art-loving circle, Caravaggio executed a number of intimate chamber-pieces —The Musicians, The Lute Player, a tipsy Bacchus, an allegorical but realistic Boy Bitten by a Lizard—featuring Minniti and other adolescent models.

Caravaggio’s first paintings on religious themes returned to realism, and the emergence of remarkable spirituality. The first of these was the Penitent Magdalene, showing Mary Magdalene at the moment when she has turned from her life as a courtesan and sits weeping on the floor, her jewels scattered around her. “It seemed not a religious painting at all … a girl sitting on a low wooden stool drying her hair … Where was the repentance … suffering … promise of salvation?” It was understated, in the Lombard manner, not histrionic in the Roman manner of the time. It was followed by others in the same style: Saint Catherine; Martha and Mary Magdalene; Judith Beheading Holofernes; a Sacrifice of Isaac; a Saint Francis of Assisi in Ecstasy; and a Rest on the Flight into Egypt. These works, while viewed by a comparatively limited circle, increased Caravaggio’s fame with both connoisseurs and his fellow artists. But a true reputation would depend on public commissions, and for these it was necessary to look to the Church.