This article considers the rise in popularity of interdisciplinary courses that explore the rich and illuminating relationships between Literature and Law, both as subjects of academic study, and for their relevance to the wider world. The history of the two disciplines in England and America is briefly traced, to gain some insight into their complex interconnectedness; from the era of classical Greece, until the twenty-first century. Consideration of the distinction developed in the Oresteia of Aeschylus, between revenge, on the one hand, and lawful justice, on the other, is followed by discussions of the interrelationship between law and literature in the philosophies of Plato and Aristotle respectively. In the era of Republican Rome, the seminal figure of Cicero, as legislator and rhetorician, is highlighted for his influence on European concepts of law and the legal profession, and the impact of his style on Renaissance humanism. William Shakespeare’s interest in legal themes and the nature of justice, is then briefly addressed. The American Founding Fathers’ passion for both literature and legal matters, is regarded as having had a profound effect on the framing of the American Constitution and the Declaration of Independence, both in style and in content. Finally, there is a brief overview of recent interdisciplinary initiatives in Departments of Law and English Literature, in Britain and the United States. The ongoing and complex connections between Literature and Law continue to offer a fruitful field, for a study whose implications have only just begun to be explored.