This period of the painter’s life, when his fortunes began to rise, also marks his first appearances in the criminal archives of Rome. He is mentioned in testimony given in July 1597 by a barber named Luca, in connection with a murky and ultimately unsolved case involving a missing cloak and a dagger:

This painter is a stocky young man…with a thin black beard, thick eyebrows and black eyes, who goes dressed all in black, in a rather disorderly fashion, wearing black hose that is a little bit threadbare, and who has a thick head of hair, long over his forehead.

Caravaggio, who wore black not because it was fashionable but probably because it enabled him to evade detection in Rome’s unlit streets at night, would be arrested on numerous occasions over the succeeding years. A strong flavour of the artist’s proud and acerbic character is conveyed by his own words in court following his detention on May 4, 1598, for bearing arms in a public place: “I was arrested last night…because I was carrying a sword. I carry the sword by right because I am Painter to Cardinal del Monte. I am in his service and live in his house. I am entered on his household payroll.”

The German etcher and art historian Joachim von Sandrart (1606–88) wrote a short account of Caravaggio during his years in Rome, remarking that he liked to go around “in the company of his young friends, mostly brash, swaggering fellows—painters and swordsmen—who lived by the motto nec spe, nec metu, ‘without hope, without fear.’ ” His friends included the painters Orsi, Minniti, and Orazio Gentileschi as well the architect Onorio Longhi, a man so hot-tempered that he would be described by a later biographer as having “a head that smoked.” Caravaggio also associated with a number of Rome’s prostitutes and courtesans, notably Fillide Melandroni, a woman from Siena who served as his model for a number of pictures painted in the late 1590s: Martha and Mary Magdalene; the startlingly sadistic-erotic Judith Beheading Holofernes, in which she saws at the neck of the tyrant with her sword in a setting more reminiscent of a Roman bordello than the Assyrian general’s tent described in the Apocrypha; and the haunting Saint Catherine of Alexandria, shown embracing the sword of her own martyrdom with the tenderness of a lover’s caress.

It was with those works, in which he placed sacred figures in a modern setting and in modern dress, using a live model posed before him, that Caravaggio perfected the method that would bring him both fame and notoriety. He also began at this time to develop his characteristically extreme technique of chiaroscuro, darkening his shadows to produce stark contrasts of light and dark, a method eloquently described by Bellori:

He went so far in this style that he never showed any of his figures in open daylight, but instead found a way to place them in the darkness of a closed room, placing a lamp high so that the light would fall straight down, revealing the principal part of the body and leaving the rest in shadow.

Caravaggio’s association with his model for these pictures, Melandroni, may have been personal as well as professional. It was illegal for women to model for painters in Rome at the time, so employing a prostitute was a convenient way of getting around the legislation. Caravaggio would be linked to a number of other prostitutes during his time in Rome, and there is circumstantial evidence to suggest that he actually operated as a pimp in the time when he was not painting for Cardinal del Monte or his other patrons: an arrangement that would have provided him with free models and casual sexual encounters on demand, as well as extra income. Caravaggio’s association with Melandroni certainly fueled the animosity that would develop, during the years that followed, with a man named Ranuccio Tomassoni. Tomassoni was Melandroni’s pimp during the years when she began modeling for Caravaggio and may well have resented the painter’s connection to her. In any case, the triangular relationship produced a simmering antagonism between the two men. Tomassoni was a dangerous man to have as an enemy, with powerful connections in the city: one of his brothers, Giovan Francesco, was caporione, or area commander, of the Campo Marzio district; another, Alessandro, was accorded the honour of being buried in the Pantheon in Rome.