Shakespeare wrote Twelfth Night near the middle of his career, probably in the year 1601. Most critics consider it one of his greatest comedies, along with plays such as As You Like It, Much Ado About Nothing, and A Midsummer Night’s Dream. Twelfth Night is about illusion, deception, disguises, madness, and the extraordinary things that love will cause us to do—and to see.

Twelfth Night is the only one of Shakespeare’s plays to have an alternative title: the play is actually called Twelfth Night, or What You Will. Critics are divided over what the two titles mean, but “Twelfth Night” is usually considered to be a reference to Epiphany, or the twelfth night of the Christmas celebration (January 6). In Shakespeare’s day, this holiday was celebrated as a festival in which everything was turned upside down—much like the upside-down, chaotic world of Illyria in the play.

Twelfth Night is one of Shakespeare’s so-called transvestite comedies, a category that also includes As You Like It and The Merchant of Venice.These plays feature female protagonists who, for one reason or another, have to disguise themselves as young men. It is important to remember that in Shakespeare’s day, all of the parts were played by men, so Viola would actually have been a male pretending to be a female pretending to be a male. Contemporary critics have found a great deal of interest in the homoerotic implications of these plays.

As is the case with most of Shakespeare’s plays, the story of Twelfth Night is derived from other sources. In particular, Shakespeare seems to have consulted an Italian play from the 1530s entitled Gl’Ingannati, which features twins who are mistaken for each other and contains a version of the Viola-Olivia-Orsino love triangle in Twelfth Night. He also seems to have used a 1581 English story entitled “Apollonius and Silla,” by Barnabe Riche, which mirrors the plot of Twelfth Night up to a point, with a shipwreck, a pair of twins, and a woman disguised as a man. A number of sources have been suggested for the Malvolio subplot, but none of them is very convincing. Sir Toby, Maria, and the luckless steward seem to have sprung largely from Shakespeare’s own imagination.

Twelfth Night is a romantic comedy, and romantic love is the play’s main focus. Despite the fact that the play offers a happy ending, in which the various lovers find one another and achieve wedded bliss, Shakespeare shows that love can cause pain. Many of the characters seem to view love as a kind of curse, a feeling that attacks its victims suddenly and disruptively. Various characters claim to suffer painfully from being in love, or, rather, from the pangs of unrequited love. At one point, Orsino depicts love dolefully as an “appetite” that he wants to satisfy and cannot (I.i.1–3); at another point, he calls his desires “fell and cruel hounds” (I.i.21). Olivia more bluntly describes love as a “plague” from which she suffers terribly (I.v.265). These metaphors contain an element of violence, further painting the love-struck as victims of some random force in the universe. Even the less melodramatic Viola sighs unhappily that “My state is desperate for my master’s love” (II.ii.35). This desperation has the potential to result in violence—as in Act V, scene i, when Orsino threatens to kill Cesario because he thinks that -Cesario has forsaken him to become Olivia’s lover.

Love is also exclusionary: some people achieve romantic happiness, while others do not. At the end of the play, as the happy lovers rejoice, both Malvolio and Antonio are prevented from having the objects of their desire. Malvolio, who has pursued Olivia, must ultimately face the realization that he is a fool, socially unworthy of his noble mistress. Antonio is in a more difficult situation, as social norms do not allow for the gratification of his apparently sexual attraction to Sebastian. Love, thus, cannot conquer all obstacles, and those whose desires go unfulfilled remain no less in love but feel the sting of its absence all the more severely.

Gender is one of the most obvious and much-discussed topics in the play.Twelfth Night is one of Shakespeare’s so-called transvestite comedies, in which a female character—in this case, Viola—disguises herself as a man. This situation creates a sexual mess: Viola falls in love with Orsino but cannot tell him, because he thinks she is a man, while Olivia, the object of Orsino’s affection, falls for Viola in her guise as Cesario. There is a clear homoerotic subtext here: Olivia is in love with a woman, even if she thinks he is a man, and Orsino often remarks on Cesario’s beauty, suggesting that he is attracted to Viola even before her male disguise is removed. This latent homoeroticism finds an explicit echo in the minor character of Antonio, who is clearly in love with his male friend, Sebastian. But Antonio’s desires cannot be satisfied, while Orsino and Olivia both find tidy heterosexual gratification once the sexual ambiguities and deceptions are straightened out.

Yet, even at the play’s close, Shakespeare leaves things somewhat murky, especially in the Orsino-Viola relationship. Orsino’s declaration of love to Viola suggests that he enjoys prolonging the pretense of Viola’s masculinity. Even after he knows that Viola is a woman, Orsino says to her, “Boy, thou hast said to me a thousand times / Thou never should’st love woman like to me” (V.i.260–261). Similarly, in his last lines, Orsino declares, “Cesario, come— / For so you shall be while you are a man; / But when in other habits you are seen, / Orsino’s mistress, and his fancy’s queen” (V.i.372–375). Even once everything is revealed, Orsino continues to address Viola by her male name. We can thus only wonder whether Orsino is truly in love with Viola, or if he is more enamoured of her male persona.

The problem of social ambition works itself out largely through the character of Malvolio, the steward, who seems to be a competent servant, if prudish and dour, but proves to be, in fact, a supreme egotist, with tremendous ambitions to rise out of his social class. Maria plays on these ambitions when she forges a letter from Olivia that makes Malvolio believe that Olivia is in love with him and wishes to marry him. Sir Toby and the others find this fantasy hysterically funny, of course—not only because of Malvolio’s unattractive personality but also because Malvolio is not of noble blood. In the class system of Shakespeare’s time, a noblewoman would generally not sully her reputation by marrying a man of lower social status.

Yet the atmosphere of the play may render Malvolio’s aspirations less unreasonable than they initially seem. The feast of Twelfth Night, from which the play takes its name, was a time when social hierarchies were turned upside down. That same spirit is alive in Illyria: indeed, Malvolio’s antagonist, Maria, is able to increase her social standing by marrying Sir Toby. But it seems that Maria’s success may be due to her willingness to accept and promote the anarchy that Sir Toby and the others embrace. This Twelfth Night spirit, then, seems to pass by Malvolio, who doesn’t wholeheartedly embrace the upending of order and decorum but rather wants to blur class lines for himself alone.

No one is truly insane in Twelfth Night, yet a number of characters are accused of being mad, and a current of insanity or zaniness runs through the action of the play. After Sir Toby and Maria dupe Malvolio into believing that Olivia loves him, Malvolio behaves so bizarrely that he is assumed to be mad and is locked away in a dark room. Malvolio himself knows that he is sane, and he accuses everyone around him of being mad. Meanwhile, when Antonio encounters Viola (disguised as Cesario), he mistakes her for Sebastian, and his angry insistence that she recognize him leads people to assume that he is mad. All of these incidents feed into the general atmosphere of the play, in which normal life is thrown topsy-turvy, and everyone must confront a reality that is somehow fractured.