Филиппо Липпи

Filippo Lippi was a friar who kept forgetting he was a friar. Orphaned young in Florence, he was placed in the Carmelite monastery by the Carmine, where as a boy he could watch Masaccio painting the frescoes that were reinventing Florentine art, solid figures with real weight in real space. Lippi took vows, but he was a painter first, and eventually the Medici, Florence's ruling banking family, kept him working almost as a private artist.

Around 1456, while serving as chaplain to a convent in Prato, he met a young novice named Lucrezia Buti and took her away from the nuns during a religious procession. The scandal was enormous. The couple had a son, Filippino, who became a fine painter in his own right, and according to the biographer Vasari it was Cosimo de' Medici himself who eventually smoothed things over and got the pair released from their vows.

Through all of it Lippi painted some of the tenderest Madonnas of the century, human-faced young women set in front of real landscapes. His most important pupil absorbed exactly that sweetness of line: Sandro Botticelli, who carried it into the next generation. Lippi died in 1469 in Spoleto, where he was at work on frescoes in the cathedral.