AbstractOne way of seeing Machiavelli is as a literary artist who appreciated, in his figurative portraiture of princes, that an effective likeness will always reveal to the attentive eye, something of the prince, of his audience, and of the portraitist himself. And since politics is an activity in which, on his understanding, there is no absolute truth, but only multifarious effectual truths; a comprehensive depiction of political life must embrace irreconcilable points of view as diverse as those of individual princes, the people, and “each man.” The observer's task thus demanded perspectival powers that would test the fabled eyes of Argus. This article sets out the evidence supporting such an interpretation in individual texts of Machiavelli's works, while suggesting how each contributes to the completed literary artistry of his brilliantly evoked world of pictures in words of political aspiration, failure and achievement.