This deeply moving image was executed about 1437–39 for private devotion. The desolate rocky wilderness—a feature of a number of Lippi's later works—suggests a landscape of renunciation and is perhaps an invitation to the viewer to forsake the world as well as a perfect foil for the tragic subject. The picture clearly was intended as an object of meditation: The grieving figure of the Virgin looks out, soliciting our empathetic response. This painting may be among those that, according to the sixteenth-century biographer Giorgio Vasari, Lippi made for Cosimo de' Medici to give to Pope Eugenius IV, who was then residing in Florence.

Although its surface has suffered from a cleaning done in the past, the picture is one of Lippi's most haunting works. It is a painted equivalent to the emotionally charged marble reliefs of Donatello.

cat. no. 2