In Thinking About Shakespeare, Kay Stockholder reveals the rich inner lives of some of Shakespeare's most enigmatic characters and the ways in which their emotions and actions shape and are shaped by the social and political world around them. In addressing all genres in the Shakespeare canon, the author explores the possibility of people being constant to each other in many different kinds of relationships: those of lovers, kings and subjects, friends, and business partners. While some bonds are irrevocably broken, many are reaffirmed. In all cases, the author offers insight into what drives Shakespeare's characters to do what they do, what draws them together or pulls them apart, and the extent to which bonds can ever be eternal. Ultimately, the most durable bond may be between the playwright and the audience, whereby the playwright pleases and the audience approves.

The book takes an in-depth look at a dozen of The Bard's best-loved works, including: A Midsummer Night's Dream; Romeo and Juliet; The Merchant of Venice; Richard II; Henry IV, Part I; Hamlet; Troilus and Cressida; Othello; Macbeth; King Lear; Antony and Cleopatra; and The Tempest. It also provides an epilogue titled: Prospero and Shakespeare.