Head of a Man in Profile Facing to the Left 1490-94 Leonardo da Vinci Italian In his studies from the late 1480s onward, Leonardo would increasingly link his exploration of human physiognomy to that of the "ages of man." While he often portrayed youth as possessing perfectly proportioned features, he would depict old age as marred by caricaturesque deformity. In this fragmentary study from about 1490-94, Leonardo began to draw the grotesque aquiline profile of an old man in charcoal or soft black chalk, as is seen in the underdrawing, but then transformed it by carefully reworking the drawing in pen and ink to portray a younger man. The most dramatic change occurs in the nose, which in the pen-and-ink drawing appears shorter and straighter. The noble mature profile in the finished form evokes the portraits of Roman emperors seen in antique medals, cameos, and coins, but it bears an uncanny resemblance to the profile of Bartolommeo Colleoni (which may not be an actual portrait of the co