So who is the inept draftsman of the Cleopatra verso, the first drawing on this otherwise magnificent sheet? I would suggest Tommaso de’ Cavalieri, the young man to whom Michelangelo offered drawing lessons and who was the first owner of the Cleopatra.
Michelangelo met Cavalieri in Rome toward the end of 1532. By all accounts, Cavalieri was extremely handsome, endowed with exquisite manners, physical grace, and a sensitive personality. Despite the difference in age and in social standing (Cavalieri was from a noble Roman family), the two experienced an instant mutual attraction and enjoyed a close friendship that lasted more than 30 years. And how did an old man (Michelangelo was considered old at 57) express his feelings for the admiring youth? With long, gushing letters, poetry, days spent looking at art together, and an offer to teach the young man drawing.
Cavalieri tried his hand by drawing the figure on the verso. Not yet a Cleopatra, the head may have been inspired by an antique sculpture that the two friends inspected together, such as the famousSleeping Ariadne in the Belvedere Court of the Vatican. Or it may have been inspired by Giovanni Boccaccio’s Famous Women: is this Agrippina, the grieving wife of Germanicus, or the Carthaginian Queen Sofonisba just after draining the fateful cup of poison? However, Cavalieri’s halting effort fell short of its classical inspiration (the display of teeth had especially negative connotations). To demonstrate “buon disegno,” Michelangelo reversed the sheet and performed a miracle of artistic alchemy: ugliness became beauty, harrowing but unbecoming emotion became serene resignation, an indecorous head was transformed into a doomed Cleopatra. We are privileged witnesses of Michelangelo turning base matter into gold.
Cavalieri kept the Cleopatra for 30 years before he was constrained to donate it to Duke Cosimo de’ Medici in 1562. In the accompanying letter, Cavalieri lamented that giving up his treasured possession was no less painful than losing a child.