Problems of individual moral choice have always been closely bound up with the larger normative concerns of political theory. There are several reasons for this continuing connection. First, the value conflicts involved in private moral choice often find themselves reproduced on the public stage: for example, states may find it difficult to do right by both justice and mercy in much the same way individuals do. Second, we frequently find conflicts among the values at stake in individual life and public life, such that the moral choice we must make is between private and public goods. Loosely speaking, choices which express these conflicts are what philosophers call moral dilemmas: choices in which no matter what one does one will be forfeiting some important moral good; in which wrongdoing is to some degree inescapable; in which one is (perhaps literally) damned if one does and damned if one doesn’t. The eight essays collected in this volume explore the philosophical problem of moral dilemmas as that problem finds expression in ancient drama, classic and contemporary novels, television, film, and popular fiction. They consider four main types of dilemmas. In the first section, the authors examine dilemmas associated with political stability and regime change as expressed in the HBO television series Deadwood and in Stephen King’s novels and short stories. The second section confronts dilemmas associated with public leadership, considering the ethical conflicts in Aeschylus’s classical dramas The Suppliants, Tolkien’s Lord of the Rings, and in the contemporary FOX television series 24. In the volume’s third section, the authors examine dilemmas of institutional evil, specifically slavery, as they emerge in Harriet Beecher Stowe’s classic novel Uncle Tom’s Cabin and in J.K. Rowling’s Harry Potter novels. Finally, the collection considers dilemmas of community and choice in Toni Morrison’s novel Paradise and in the contemporary film A Simple Plan.