This is one of the few authenticated drawings of Michelangelo and was drawn for Tommaso de’ Cavalieri, a young artist that Michelangelo passionately loved. This is the only drawing, of what Michelangelo claimed many drawings presenting to Cavlieri, that we have left. The drawing is a study for a bust of Cleopatra and possibly represents the conflicted nature of Michelangelo’s love for Cavalieri since Cleopatra was widely understood in the Renaissance as immasculating Caesar and later Marc Antony with her beauty.