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Caravaggio's stay in Rome helped him learn more about art. He was drawn to all the famous artists that lived there but because he had little money Caravaggio had to find work assisting other painters and his personal career didn't launch right away. After showing off his talents in a series of Roman studios he began to build a reputation for himself, forming friendships with influential figures in the art world, until he met the man who fully recognized his talents and led him on the road to success. .
Around 1595, Caravaggio started selling his paintings through a dealer and soon caught the attention of influential figures in the art world like Cardinal Francesco de Monte. Monte invited the painter to stay in his courtyard, which proved to be a major step in his success. Caravaggio became known for his remarkable speed (often completing a painting in just two weeks). Under Monte's guidance, Caravaggio already had 40 works to his name. These paintings were very significant in launching his career. .
Caravaggio's early work depicted evocative pictures of young boys done up as angels, his favorite saint, John the Baptist, still-life's, genre scenes, and self portraits. His only known assistant was Cecco, who often appears in Caravaggio's work and is believed to have been his lover. .
In 1597, Caravaggio was given the opportunity to decorate the Contarelli Chapel in the Church of San Luigi dei Francesi in Rome. This assignment was very important for the 26-year-old artist. Commissioned to paint three large scenes from St. Matthew's life ("St. Matthew and the Angel", "The Calling of St. Matthew", and "The Martyrdom of St. Matthew") was one of the biggest jobs he'd ever been asked to do. The paintings were finished in 1601 and showed off how talented Caravaggio was. After these paintings he started to paint more religious scenes in his own dark, humanistic style.