Caravaggio traveled to Rome, as many aspiring artists did, in search of work. The newly elected pope, Clement VIII, was determined to transform the city into the visible symbol of a revived and flourishing Catholic faith. New churches were being built and old churches remodeled, with altarpieces and sculptures commissioned in great numbers. At a rough estimate, about 2,000 artists lived and worked in the city, out of a total population of 100,000. They had their own quarter, an area of approximately two square miles between the Piazza del Popolo and the Piazza di Spagna, where they clustered in distinct communities according to their place of origin. Competition between the different groups, and between individual artists, was intense and frequently flared up into feuds and vendettas. Rome was a city of migrants—priests seeking preferment, pilgrims seeking salvation, mercenary soldiers seeking employment—as well as a place where social distinctions were more fluid than in other, more-feudal parts. Many hoping for fame and fortune in that opportunistic environment pretended to a higher social status than their birth merited and behaved according to a debased version of the old chivalric codes of honour, whereby the slightest perceived insult or injury was met with force. Caravaggio’s many fights and disagreements with others fit into that wider pattern of violence, so it would be wrong to see his behaviour, however apparently erratic, as freakish or exceptional.

To judge by the different accounts provided by his first biographers—Giovanni Baglione and the aforementioned Bellori and Mancini, all writing within living memory of Caravaggio—the artist’s early years in Rome were unsettled. At the start he lodged with a jobbing painter from Sicily named Lorenzo Siciliano, in whose workshop, says Bellori, “Caravaggio painted heads for a groat apiece and produced three a day.” Mancini reports that during that period Caravaggio also lodged with a beneficed priest of St. Peter’s named Pandolfo Pucci, whose hospitality left much to be desired: “He was given nothing but salad to eat in the evening.…After a few months he left…calling his benefactor and master ‘Monsignor Salad.’ ”

Caravaggio next spent some time in the studio of a minor Sienese painter called Antiveduto Grammatica. Then he moved to the workshop of Giuseppe Cesari, also known as Cavaliere d’Arpino, who was one of the most-prominent artists in Rome during the 1590s. Cesari was responsible for a number of monumental altarpieces and decorative schemes but employed Caravaggio merely to paint decorative borders or embellishments to his work: pictures of “flowers and fruit.” According to Bellori, Caravaggio resented the restriction to such lowly subject matter: “As he was working at these things against his will and feeling great regret to see himself kept from figures, he welcomed the opportunity offered by Prospero.” Two pictures by Caravaggio survive with a provenance that links them to the Cesari workshop: Boy with a Basket of Fruit and Self-Portrait as Bacchus (also called Sick Bacchus). Both were expropriated from Cesari by Scipione Borghese, the papal nephew, in the early 1600s and have remained in the Borghese collection ever since. They are subtle and bittersweet works, the first perhaps inspired by the divine longing of the Bridegroom in the Song of Songs, the second by the ancient association between art and the Roman god of wine and creative abandon. Given that each remained with Cesari after Caravaggio’s departure, it is possible that they had been painted as demonstration pieces: proof to his master that he could indeed paint more-ambitious subjects than flowers and fruit alone.

The artist’s time with Cesari appears to have ended badly, with an obscure accident involving a kick from a horse that left Caravaggio in the hospital of Santa Maria della Consolazione. According to Mancini, at about the start of 1595, after eight months in the Cesari workshop, he lodged with another priest: “Monsignor Fatin Petrigiani, who gave him the comfort of a room in which to live.” At about that time he met Prospero Orsi, a painter of grotesques, who (according to Bellori) encouraged Caravaggio to strike out on his own and paint directly for the market. Baglione adds that Caravaggio painted a number of self-portraits at that time—now presumed lost—and “a boy bitten by a lizard emerging from flowers and fruits; you could almost hear the boy scream, and it was all done meticulously.” The subject is dramatic, as might be expected of a work intended to pique the interest of Roman connoisseurs: a young man in a state of undress, picking at a bowl of fruit, is rudely interrupted by a lizard that bites his finger. It may have been intended as a parable of the punishments that attend the lascivious, with the snapping lizard symbolizing the pains of venereal disease.