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Abstract: The account of Pietropaolo, apprentice to the barber Marco Benni, regarding the musician Angelo Tanconi when attacked by unknown assailants in 1597 is particularly useful in dating the arrival of the painter in Rome, but can also represent a window onto the world of contemporary barbers. The biographical details of Pietropaolo Pellegrini and of the Angelo’s brothers (who worked in the family barbershop) are extremely valuable for the understanding of significant aspects of the barber’s profession, which has never been sufficiently studied in the contexts of the time and place of this investigation: the area of via della Scrofa at the end of the 16th century. Official documents of the time contain information about apprenticeships, the entrance exam for the Universitas barbitonsorum, the transferral of barbers from one shop to another, while legal documents show the role of barbers within the law courts and the procedure within those courts in which a barber would testify to wounds that he had medicated. An evolution of the barber’s profession can be traced by following the documentary sources, a profession which would eventually combine basic services like the trimming of hair and beards with minor surgical operations and, around the end of the century, the buying and selling of works of art. The close vicinity of the barbershop of Sant’Agostino, which in 1597 Caravaggio had visited to have an injured leg cured and his hair trimmed, with the studio of the painter Lorenzo Carli in via della Scrofa, where Caravaggio had worked during the period immediately after his arrival in the city, was the hub for a tightly woven tapestry of interests, friendships, rivalries, and cultural and intellectual exchanges which connected the world of the barbers with that of artists.