Piero di Cosimo was in some ways the most individual of the major Florentine masters of the late quattrocento. Trained as a workshop assistant for Cosimo Rosselli, from whom he took his name, Piero accompanied Rosselli to Rome and painted the landscape background in Rosselli's fresco of The Sermon on the Mount, commissioned by Pope Sixtus IV for the Sistine Chapel. Piero's early work showed the influence of Leonardo and Filippino Lippi, and then from around 1490 the more bulky forms of Signorelli, and Netherlandish landscapes.

According to Vasari, he was a peculiar and absent-minded genius who preferred to live and work by himself, eating only the hard-boiled eggs that he prepared fifty at a time while boiling the glue he used for making size. Irritated by flies, church music, screaming children and the coughing of old men, frightened of thunderstorms and intent on allowing his property to fall into disrepair, he died in self-imposed solitude, afflicted by a partial paralysis that had prevented him from working for some time.

The present work compares closely to a tondo by Piero previously at North Mymms Park (sold in these Rooms on 24 April 2009, lot 95) dated by Dennis Geronimus to circa 1490-1500 (Piero di Cosimo: Visions Beautiful and Strange, London, 2006, p. 263, fig. 205). In both works, the stony wilderness of the striated rock that frames the Virgin and her infant was highly original and shows the impact Leonardo da Vinci’s contemporaneous painting had on Piero. In both works, Mary and Christ are captured in a tender embrace, while Joseph emerges from a cavernous hermitage to cast his gaze over the horizon.