Best Books About Moral Dilemmas by William Shakespeare
Introduction: The Choices That Make the Man
William Shakespeare is the greatest dramatist of the moral dilemma - the writer who put conscience itself on the stage. His tragedies are built on choices: Hamlet’s choice whether to avenge his father, Macbeth’s choice whether to seize the crown, Othello’s choice whether to believe the lie, Lear’s choice of whom to trust. Shakespeare does not tell us the right answer; he shows us the choice being made, and the consequences unfolding, with a fairness to every side that has made his dilemmas inexhaustible for four centuries.
This guide maps Shakespeare’s plays of moral dilemma, from the essential tragedy of the choice itself to the companion plays of ambition, jealousy and judgment, with a reading order, honest content notes, the themes that make his work cohere, and companions for when you want more.
The Moral Plays in Reading Order
Hamlet (c. 1600) is the essential Shakespeare, and the play of the moral dilemma itself: Hamlet, the prince of Denmark, is told by his father’s ghost that his uncle Claudius murdered him - and must decide what to do. The play is the dilemma: every option - action, delay, feigned madness, murder - is weighed and found wanting, and Hamlet’s famous soliloquies are thinking made visible. The play’s question - “To be, or not to be” - is the question of whether to act or endure, and the whole tragedy is the cost of a conscience that cannot choose. It is the most studied work in the English language, and it remains the essential entry into Shakespeare’s moral world. Content note: a tragedy dealing with murder, madness and death; for readers from around age fifteen upward.
Macbeth (1606) is the essential companion, and the play of the choice made: Macbeth, a brave general, is told by witches he will be king - and chooses to make the prophecy true by murdering the king who trusts him. The play is the anatomy of a moral decision: the temptation, the hesitation, the act, and the long aftermath of guilt, paranoia and more killing. It is the shortest of the great tragedies and the most concentrated statement of Shakespeare’s question - what a person becomes when he chooses wrong knowing it is wrong. Content note: a tragedy dealing with murder and its psychological cost; for readers from around age fifteen upward.
Othello (c. 1603) is the essential companion about the dilemma of trust: Othello, a general and a Moor in Venice, is persuaded by his ensign Iago that his wife Desdemona has been unfaithful - and must choose between the lie he is told and the love he knows. The play is the dilemma of jealousy: the choice to believe the accusation, and the murder that follows from a false belief held as certainty. Content note: a tragedy dealing with jealousy, racism and murder; for readers from around age sixteen upward.
The Merchant of Venice (c. 1596) is the essential companion about the dilemma of justice: Shylock, a Jewish moneylender, holds Antonio to a bond of a pound of flesh, and the courtroom becomes the dilemma of mercy versus law - the play in which Shakespeare asks whether justice without mercy is justice at all. Content note: a play containing antisemitism in its depiction of Shylock, which should be discussed with historical awareness; for readers from around age fifteen upward.
Content Notes for Each Play
Shakespeare’s tragedies deal with murder, madness, jealousy and death - the darkest human realities, dramatized without flinching. None of it is gratuitous; the violence is the consequence of the choices, and that is the point. The plays are usually encountered from around age fifteen upward, with a good annotated edition or, better, a performance. The Merchant of Venice requires particular care: its antisemitic elements are part of its history, and readers should encounter the play with awareness and discuss rather than ignore them. The plays are short - each runs a few hours in performance - and they reward rereading and, above all, watching.
Readers choosing among Shakespeare’s plays will find our purpose and meaning themes and values guide helpful for the larger questions his dilemmas raise, and our responsibility and duty themes and values guide useful for the obligations his characters face.
The Moral Themes in Shakespeare’s Work
Three themes give Shakespeare’s treatment of moral dilemmas its distinctive shape.
The choice as the action is his central claim. Shakespeare’s greatest innovation is to make thinking dramatic: Hamlet’s soliloquies are not pauses but the action itself, and the play is the choice, not the deed. His dilemmas are the ones in which deciding is the event, and the cost of deciding badly is the tragedy.
Conscience and its cost is the second theme. Shakespeare’s characters pay for their choices - Macbeth’s guilt, Othello’s despair, Hamlet’s deaths - and his plays are the argument that the conscience is the real arena, and that no choice is free. His morality is the drama of consequences, unfolding with remorseless logic.
The end versus the means is the third theme. Macbeth’s crown, Othello’s certainty, Shylock’s bond - Shakespeare’s dilemmas are the ones in which the desired end is weighed against the means, and his plays answer the weighing with the price. His morality is the argument that the means become the end, and that the person is made by the choice.
Why Shakespeare’s Morality Endures
Hamlet and Macbeth are performed somewhere in the world every day, and Shakespeare’s phrases - “To be, or not to be,” “the lady doth protest too much,” “out, damned spot” - have entered every language. The reason is simple: Shakespeare wrote about moral dilemmas at the scale of one person’s choice, and made the largest questions of ethics feel like a soliloquy you could speak. His characters are not emblems but people - Hamlet both paralyzed and brilliant, Macbeth both villain and sufferer - and his fairness to them is why four centuries of readers return.
His influence extends far beyond literature: psychology, philosophy and law all draw on his cases, his dilemmas are the standard material of education, and his characters have become the archetypes through which we still think about choice. But the plays endure because of their completeness - a moral seriousness that never becomes a lesson, a darkness that never becomes despair, and a sympathy that extends even to his murderers. Shakespeare wrote the essential dramas of the moral dilemma, and no one has written better ones since.
Companion Books for Every Shakespeare Reader
When you have finished Shakespeare’s own plays, these titles extend the same territory.
The Oresteia by Aeschylus (458 BC) is the essential companion as the ancestor: the Greek trilogy of murder, vengeance and the founding of justice - the dilemma of the blood-feud that Shakespeare’s tragedies descend from.
Crime and Punishment by Fyodor Dostoevsky (1866) is the essential companion as the heir: Raskolnikov’s theory and its cost - the novel that took Shakespeare’s question of the choice and the conscience into the modern city.
All My Sons by Arthur Miller (1947) is the essential companion as the modern tragedy: the businessman who shipped faulty parts and the price his family pays - the moral dilemma of the means and the end, in a contemporary setting.
For the practical questions of what the choices are for, our best purpose and meaning reading list and our best responsibility and duty reading list gather the framing readers need.
A Reading Plan for Book Clubs
Hamlet is the ideal Shakespeare for a club: short enough to read in a week, famous enough that everyone comes with expectations, and deep enough to generate months of discussion. The most fertile questions are the ones the play refuses to settle: Is Hamlet’s delay a flaw or a wisdom? What would the right choice have been - and is there one? What does the play think about thinking?
Macbeth is the companion for the opposite discussion: the choice made, the conscience afterward. The book also generates the hardest kind of conversation: the claim that we are made by our choices - which forces every member to examine their own. Clubs should consider watching a filmed performance after reading; Shakespeare’s dilemmas are completed on the stage.
Clubs preparing without spoilers will find our a thoughtful guide to purpose and meaning useful for framing the themes.
A Note on the Book’s Structure and Editions
Shakespeare wrote for the stage, not the page, and the plays reward reading with performance in mind: the soliloquies are speeches to be spoken, the scenes are built for exits and entrances, and the “book” is a script. Readers should know that the texts exist in multiple versions - the quartos and the Folio - and that modern editions like the Arden and the Folger present the differences honestly. Hamlet is the longest of the tragedies, and the “To be, or not to be” soliloquy is the play’s center; Macbeth is the shortest, built for speed. Both reward rereading, and both reward watching; the second encounter is where the dilemmas become yours.
What Shakespeare’s Plays Teach Together
Read together, the four plays form a single anatomy of the moral dilemma, each one a different phase of the choice. Hamlet supplies the deliberation - the conscience weighing every option, thinking as the action. Macbeth supplies the commission - the choice made, and the long cost of guilt. Othello supplies the deception - the dilemma of trust, the false belief held as certainty. The Merchant of Venice supplies the judgment - the courtroom, the pound of flesh, mercy against law. Each play is a phase of the same process - the weighing, the doing, the believing, the judging - and together they form the most complete anatomy of moral choice in literature. That is why they belong on the same shelf: the reader who has watched Hamlet deliberate, Macbeth act, Othello believe and Portia judge has seen the whole arc of the moral life, from the first hesitation to the final verdict.
Conclusion: The Choice That Makes the Person
William Shakespeare’s contribution to the literature of moral dilemma is a single demonstration, and it has entered the language: we are made by our choices. He wrote it into the conscience of a prince and the ambition of a general and the jealousy of a husband, and it has outlasted every moral system since. His dilemmas are not puzzles but actions - the choice weighed, the choice made, the cost paid. His plays are short, and they are inexhaustible. Read them, and let Shakespeare show you what choice is actually for. For more reading paths, explore the Ideas section of our site.
