What distinguishes the rule of law from the lawless, arbitrary rule of brute force — which can almost interchangeably be described as tyranny or as anarchy — is that in a lawful rule the government’s coercive power operates according to principles of generality, regularity, fairness, rationality and public-orientation, whereas the arbitrary or lawless ruler wields power in the service of his (or their) own self-interest, or by mere ipse dixit. Law is to arbitrariness as reason is to mere will. In this paper, I explore the dichotomy between lawful and arbitrary rule as it has been represented in literature. I examine first the primal foundation of lawful rule, as depicted in Aeschylus’ Oresteia, in which law is generated by domesticating the use of force, through persuasion and willing union. Athena creates lawful order, not by fiat, but by marrying the Furies to “Persuasion”: the ambient coercive powers of the people — morally justified, yet dangerously personal urges for vengeance — will now be rationalized in accordance with public, logical, and articulable principles. By contrast, in Shakespeare’s Richard III, we witness the subversion and near-destruction of lawful order by a man who will tear apart the newly framed lawful order and make the state serve his own private ends. The contrast of these two dramas reveals that the tyrant is essentially a solipsist: his ultimate goal is to make the real world obey his say-so. And if law is like love, the tyrant is like the rapist: the forced surrender of intimacy is the best facsimile of love the solipsist can create; but it can never actually be love, because the two are separated by the same invisible and impenetrable boundary that separates truth from falsehood, or genuine loyalty from the rule of terror.I conclude with a look at the dissenter living in a lawless order, as depicted in two variations on the story of Antigone — the first by Sophocles and the second by Jean Anouilh. In both, the lawless, arbitrary rule is challenged in the name of law, and in each, the ruler nearly succeeds in substituting his private realm of mere words for the public realm of actual things. What emerges from this study is that the basic premise of all lawful order — the root of all secure liberty — is that there is a gap between the will of the ruler and the genuine law. Whenever such a gap exists — whenever it is meaningful to deliberate over whether the ruler’s commands are, in fact, law — the society will, to that extent, become one of lawful order and of (at least some) freedom. The link between tyranny and solipsism is that where the ruler’s will is accounted the law, there can be no genuine law, and thus no freedom. The paradox whereby tyranny is lawless is explained by the fact that tyranny is an attempt to impose by convention what does not originate in nature — and in the end, neither physical nature nor the nature of human relationships can be subjected to such commands. The ultimate demand of the lawless ruler(s) is to substitute his (or their) word for the world — to compel the subject to love him (or them). And because that can never be accomplished, arbitrary rule is doomed to eventual collapse.