The Winter's Tale is a perfect tragicomedy. Set in an imaginary world where Bohemia has a seacoast, and where ancient Greek oracles coexist with Renaissance sculptors, it offers three acts of unremitting tragedy, followed by two acts of restorative comedy. In between, sixteen years pass hastily, a lapse which many critics have taken as a structural flaw, but which actually only serves to highlight the disparity of theme, setting, and action between the two halves of the play. The one is set amid gloomy winter, and illuminates the destructive power that mistaken jealousy exercises over the family of Leontes, King of Sicilia; in the second half, flower-strewn spring intervenes, and all the damage that the King's folly accomplished is undone—through coincidence, goodwill, and finally through miracle, as a statue of his dead wife comes to life and embraces him.

As the force behind the tragedy stems from Leontes's belief that his wife, Hermione, and best friend, King Polixenes of Bohemia, are lovers, so Leontes has attracted more critical interest than any other character in the play. An Othello who is his own Iago, he is a perfect paranoiac, convinced that he has all the facts and ready to twist any counter-argument to fit his (mistaken) perception of the world. Perhaps because of its uncertain origin, Leontes's madness is a terrifying thing: he becomes a poet of nihilism, demanding, when told that there is "nothing" between Hermione and Polixenes, "Is this nothing? / Why, then the world and all that's in't is nothing, / The covering sky's nothing, Bohemia nothing, / My wife is nothing, nor nothing have these nothings, / If this be nothing"(I.ii.292-296). The roots of his jealousy seem to run too deep for the play to plumb—there are hints of misogyny, of dynastic insecurity, and of an inability to truly separate himself psychologically from Polixenes, but no definitive answers. Indeed, the only answer is his own—in one of Shakespeare's finer images, Leontes says "I have drunk, and seen the spider"(II.i.45).

To balance his morbid, brooding nihilism and sexual jealousy, Shakespeare makes Leontes's daughter Perdita a poet of spring, rebirth, and revitalization, whose own lover (Polixenes's son Florizel) is as constant and generous as Leontes is suspicious and cruel. She appears decked in flowers, and when she dispenses them to everyone around her, the play links her with Proserpina, Roman goddess of the spring and growing things. If Leontes is a tragic hero, then she is a fairy-tale heroine, a princess reared among commoners who falls in love with a prince and—eventually—lives happily ever after. Leontes casts her out as an infant in Act III, when he is in the grip of darkness; in Act V she returns to him, and restores him to happiness. The miracle of Hermione's resurrection at the play's close is only a fitting close to the spirit of rebirth that Perdita brings into the story.

The play is also notable for its rich group of supporting characters. Hermione is an exemplary and eloquent figure, despite the fact that she spends the play defending herself against unjust accusations, and her friend Paulina is the voice of sanity while Leontes is mad and then the voice of reminder and penance once he regrets his crimes. The rustic Shepherd who takes in Perdita and the ever-faithful lord, Camillo are both sympathetic characters, too, but none can match Autolycus, the peddler, thief and minstrel who is a harmless villain (he robs, lies, and cheats)—so harmless, in fact, that the audience forgives and even applauds him as he sings, dances, and robs his way through the play, contriving even to find time to provide a helping hand to the other characters as they struggle toward their happy ending.