During the Italian Renaissance, artists sought to recreate portraits of the ancient king of Macedon, Alexander the Great, that were faithful to the classical visual and literary sources. Not only does this interest in the likeness of the king reflect a desire to revive the art of antiquity, but, through the recreation of a likeness of the Macedonian monarch, a modern artist could compete with and appropriate the famed legacy of Alexander’s court portraitists, Apelles, Lysippus and Pyrgoteles. This paper explores the interest in portraits of Alexander during the Renaissance, tracing literary and visual models used by artists, the images produced, and the multivalent implications that such works offered artists, patrons, and viewers alike.