Troilus and Cressida is one of Shakespeare’s later plays, written shortly after Hamlet (1600–1601), but before the other great tragedies. Composed around 1602, it was probably performed in the winter of 1602–1603, but no record of the performance survives, and the play itself was not published in a collection for another six years. For these reasons, several critics have suggested that it was performed only once, or perhaps not at all. Scholars have also speculated that some of the characters in the Greek and Trojan armies may have been thinly disguised caricatures of contemporaries, either other playwrights or members of King James’s court. If so, and if these caricatures caused sufficient offense, they may have resulted in the play getting a severely limited stage run.
    
The genre classification of Troilus and Cressida has been in dispute from the beginning. In the Quarto edition of 1609, it was labeled a history. However, in the First Folio edition of 1623, the title specifically refers to the play as a tragedy. To add further complication, the early Quarto edition featured an anonymously authored preface that repeatedly describes the play as a comedy. Although “comedy” could simply mean “play,” the author clearly implies that this work is comical in the more modern sense. In truth, the play doesn’t fit comfortably in any of these categories. The subject matter isn’t strictly historical, since it deals with a legendary war. Cressida’s betrayal of Troilus is tragic, but not in the traditional sense that would require both to die at the end. And though there are indeed humorous moments in the play, Hector’s onstage murder breaks the usual rule that forbids the death of any key characters. Today, the conventional solution is to group Troilus and Cressida with the so-called “problem comedies,” which include Measure for Measure and All’s Well That Ends Well. All three share a dark, bitter wit and a pessimistic view of human relations that contrast sharply with earlier, sunnier comedies like Twelfth Night and As You Like It.

Sources for the play include classical mythology and Homer’s Iliad, which contains the Achilles–Hector story arc. The romance of Troilus and Cressida is derived from pseudo-Homeric medieval sources, and from Geoffrey Chaucer’s great fourteenth-century epic, Troilus and Criseyde. True to form, Shakespeare used only the bare bones of these stories for his play, and he emphasized the Elizabethan idea of Cressida’s falseness over Chaucer’s more sympathetic interpretation. In reading Troilus and Cressida, it is important to remember the popularity of all these stories in Shakespeare’s time. For the audience, the story of Troy was well known, and the events of the play, including the denouement, would have been expected from the beginning: Cressida’s treachery and Hector’s death would have been as predictable as the sinking of the Titanic is for moviegoers today.