The Merchant of Venice is Shakespeare's most troubling comedy, written in the mid-1590s. The merchant Antonio borrows money from the Jewish moneylender Shylock so his friend Bassanio can court the heiress Portia – signing a bond that forfeits a pound of his flesh if the loan is not repaid. When Antonio's ships are reported lost, Shylock demands his bond in open court, and Portia, disguised as a young lawyer, defeats him on a technicality: he may take his flesh, but not one drop of blood. Shylock leaves the play ruined and forcibly converted, while the lovers' ring-plot comedy plays out in Belmont.

The Merchant of Venice was written around 1596–1598 – it is listed among Shakespeare's plays by Francis Meres in 1598 – and first printed in quarto in 1600. The bond story comes from Giovanni Fiorentino's Italian tale Il Pecorone, and the three-caskets test from the medieval Gesta Romanorum. Shakespeare wrote it for a London that had officially expelled its Jews three centuries earlier, and in the shadow of the 1594 trial and execution of Roderigo Lopez, Elizabeth I's Portuguese-Jewish physician.

The First Folio classes it as a comedy, and it has a comedy's architecture: lovers, disguises, riddling caskets, a triple wedding and a moonlit fifth act. But the play's emotional centre is Shylock, whose destruction in the trial scene reads to modern audiences as anything but comic. Since the nineteenth century, productions have increasingly played him sympathetically, and the play is now often treated as a problem play – a comedy whose greatest scenes are the ones that refuse to be funny.

Both readings are in the text, which is why the part attracts great actors. Shylock is the play's villain by plot function: he sharpens his knife in open court to kill a man. But Shakespeare gives him the play's most humane speech – "Hath not a Jew eyes?" – and a catalogue of real grievances: Antonio has insulted and spat on him, the Christians steal his daughter and his money, and the court that defeats him strips his wealth and forces his conversion. The play lets audiences choose, and four centuries of performance have chosen differently.

The Merchant of Venice is widely taught at GCSE and Key Stage 3 in the UK, and appears at A-Level, on AP English Literature (US), the IB Diploma, and undergraduate courses worldwide – often alongside discussion of how to handle its antisemitism honestly in the classroom. This study guide is written to support all of these levels, with modern English translation, scene-by-scene analysis, character profiles, theme guides, and key quotes.

The Merchant of Venice has given English some of its most familiar phrases. Among the most quoted: "The quality of mercy is not strained", "Hath not a Jew eyes?", "If you prick us, do we not bleed?", "All that glitters is not gold", "The devil can cite Scripture for his purpose.", and "In sooth, I know not why I am so sad". Each is analysed in depth on the key quotes page.