Florentine Fra Filippo Lippi (Florentine, c. 1406-69) never should have been a monk, although after being left an orphan as a small child, with numerous siblings and with no relative to support him, he was sent to the Carmelite convent, where he was educated and took vows at age 16.
It was while he was there, watching Masaccio paint the Cappella Brancacci that he took up drawing. He showed enough talent for the prior allowed him to leave the convent in 1432 to study art (and earn enough money, he said, to fund the dowries of his six neices). Unusually, he seems to have learned his craft by his one, gradually developed an elegant, delicate line all his own.
The young friar went to Naples soon after, where he may or may not have been abducted by Barbary pirates. His picaresque life, at least according to Vasari was full of rascally escapades, lawsuits, and forgeries. By 1438 he was in the employ of the Medici, who would intervene and get him out of several jams. At one point, the Elder Cosimo de' Medici had to lock him up in room to force him to complete a commission, but even then Filippo escaped out the window by a rope made of his sheets.
Images by PD Art