Leonardo’s (1452-1519) researches on facial deformations and physiognomies seem to belong to his early Milanese days and thus are to be related to after about 1482. 

Leonardo’s famous ‘grotesque heads,’ and much of the tradition inspired by him from the 16th to the entire 18th century, cannot properly be called ‘caricatures’ in the meaning usually assigned to this kind of drawing, that is, depictions that induce a smile or mockery, nor are they, strictly speaking, ‘grotesque heads,’ in which zoomorphic or phytomorphic elements are often associated with human elements, which also may have symbolic, erotic or pagan implications. 

Leonardo’s are rather loaded heads in which physiognomic aspects are accentuated to emphasize characters, peculiarities, vices or virtues of the character. 

The drawing, which came from the Venetian antiquarian market (Piero Scarpa), was purchased by Giancarlo Ligabue in the 1970s. It was first attributed to a Leonardo artist by Cogliati Arano (2005) and then, following laboratory analysis by Paolo Spezzani (Cogliati Arano, Spezzani 2007), assigned directly to the Vinci artist. 

The monstrous face of the toothless old woman depicted here, with its nose flattened upward, drooping lips, wrinkled double or triple chin, hair pulled back and gathered in a veil stopped by a wreath with a large flower, finds no precise equivalent in the series of grotesque heads drawn by Leonardo, seeming to this day to be a truly astonishing unicum.