How does this artwork elucidate its History?
In the 1590s, Caravaggio was working in Rome, and his success and wealth were increasing. However, the time in which he painted the two versions of the Medusa was characterized by several run-ins with the law.  In July 1597, Caravaggio and his partner Prospero Orsi became involved as witnesses in a crime that occurred near San Luigi de' Francesi. In one instance, a barber named Luca gave a testimony about Caravaggio where he provided a description regarding his mysterious attire:  "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." At the time, there was an unsolved case in which two items were reported as being missing—a dark cloak and a small dagger. As a result of his mysterious behavior and affiliation with cloaks, Caravaggio was arrested several times. He told authorities that he liked dressing in dark attire to avoid drawing unnecessary attention to himself, which was also why he preferred to make late night trips. On May 4, 1598, he was arrested again for possessing a sword in public, and defended himself by saying:   “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.”   
Caravaggio's paintings were never in tune with the idealized themes that were prevalent during the time period. Instead, he became more intrigued with the idea of realism and incorporated it into his paintings such as Boy with a Basket of Fruit, The Fortune Teller, The Cardsharps, Bacchus, and even The Musicians, which were all painted within the same time period. When he painted Medusa, Caravaggio hit a great milestone in his life - he was given a chance to decorate the Contarelli Chapel, in which he created realistic images regarding the life of St. Matthew himself. Some of these paintings include Saint Matthew and the Angel, The Martyrdom of Saint Matthew, and The Calling of Saint Matthew. This opportunity to paint the chapel gave him great advantage and a sense of motivation to incorporate more realism in his artworks.
Saint Matthew and the Angel Prospero Orsi The Martyrdom of Saint Matthew Medusa Boy with a Basket of Fruit Cardinal del Monte San Luigi de' Francesi The Musicians Rome The Cardsharps Caravaggio Bacchus The Calling of Saint Matthew The Fortune Teller Contarelli Chapel