Cigoli trained in Florence under Alessandro Allori; later he was influenced by the most prominent of the Counter-Maniera painters, Santi di Tito, as well as by Barocci. The leading painter in Florence at the end of the 16th century, Cigoli shed the shackles of mannerism and infused his later paintings with an expressionism often lacking from 16th-century Florentine painting. A number of important altarpieces for various Florentine churches throughout the late 1580's and 1590's culminated in his masterpiece, the Martyrdom of Saint Stephen, painted in 1597 for the convent of Montedomini. In 1604 Cigoli moved to Rome, where he received some of the most prestigious artistic commissions given, including altarpieces for St. Peter's, Santa Maria Maggiore and San Paolo.
Like a number of his Florentine contemporaries, Cigoli placed great emphasis on his drawings, both as preparatory studies for his canvases and as technical exercises in their own right. The historian and biographer Filippo Baldinucci, an avid collector of the artist's drawings, credits Cigoli with reestablishing the principles of life drawing among the painters of Florence. Using both nude and draped models posed in the studio, Cigoli's studies from life - invariably executed in red chalk - are an integral part of his graphic output.