R: A man tricked by Gypsies

The man at the centre of this drawing is surrounded by a band of Gypsies in traditional dress. He raises his right arm to have his palm read by the old woman in traditional Gypsy dress on the right – unfortunately the sheet was cut at an early date and the palm-reading trimmed off. While the man is distracted, the grinning Gypsy on the left reaches under his sleeve to steal his purse. The two figures behind stare with hooded brow or laugh hysterically, adding to the sense of claustrophobic menace.

Gypsies had arrived in western Europe around 1420, claiming to be penitent pilgrims from Egypt but soon acquiring a reputation for fortune-telling and theft. Leonardo’s drawing dates from a period of particular hostility to Gypsies in Milan, and they were banished from the Duchy of Lombardy in April 1493, the first such edict in Italy. The drawing was therefore a satire on current affairs, probably made for the entertainment of the Sforza court. It seems to have left Leonardo’s hands and became one of his best-known compositions, serving as the basis for paintings by Giorgione and (possibly) Albrecht Dürer in Venice and Quentin Massys in Antwerp. By the 1580s it was in circulation in Milan and was presumably acquired then by Pompeo Leoni, separately from Melzi’s inheritance. The young Caravaggio was serving his apprenticeship in the city at that time and may have known the drawing, and indeed this was to become a common subject in Caravaggesque painting across Europe in the seventeenth century.

Throughout Leonardo’s life, and particularly in the years around 1490, he sketched countless grotesque heads. They can be seen as a counterpart to his investigations of ideal human proportion, distorting those ideals of beauty to create images of ‘ideal ugliness’. Leonardo had no intention of introducing such grotesques into his writings or his paintings – they were essentially amusements, for himself and his associates, and probably for the Sforza court too.