Clearly, this play contains strong tragic elements. It offers a bleak view of the world, in which the forces of love and justice are undone by circumstances and cruelty, and it ends with the death of a major heroic figure (Hector) and the betrayal of another (Troilus). But while these elements give the play strong tragic resonance, it does not fit the mold of classical tragedy followed by Shakespeare's later works, such as King Lear, Antony and Cleopatra, and others. First of all, there is no clear tragic hero—Hector's death resembles the murder of Julius Caesar, among others, but Hector himself is not the hero of the play. That honor seems like it should belong to the title character, Troilus, but Cressida, the woman who would have become his tragic heroine—Cleopatra to his Antony, or Juliet to his Romeo—elects not to die, or even to be faithful, choosing to betray him instead. His realization of this betrayal might be considered to constitute a tragic illumination, but this illumination is not followed by death, which would be the expected ending of such a tragedy. Indeed, the unsympathetic nature of the characters and the deliberately anticlimactic style that Shakespeare employs, make the play seem almost like a black comedy—or better, a tragicomedy.

The story of the siege of Troy is one of the foundational works of western civilization, and its figures—Achilles, Hector, Ulysses, Ajax, and others—are usually portrayed as larger than life. In this play, however, they are ruthlessly stripped of their heroic pretensions. While their rhetoric soars, their behavior reveals them to be a collection of brutes and braggarts. Hector manages to come through with most of his heroism intact, but Achilles—the greatest of the Greek warriors in Homeric legend—behaves like a cowardly thug, sulking in his tent and then killing Hector with a gang of comrades when Hector is unarmed. Ajax is portrayed as a less intelligent version of Achilles, Agamemnon is unable to keep order in his army, Diomedes is driven by lust—and the women fare even worse. Instead of being beautiful and virtuous, both Helen and Cressida are described or depicted as fickle and shallow, willing and eager to be unfaithful, far from any traditional feminine ideal. This overall degradation has as its narrator Thersites, the unpleasant slave who becomes a kind of moralist, since he is the only one to point out the gap between the words of these "heroes" and their behavior.

Judging from its title, Troilus and Cressida would seem to be a tragic romance, like Antony and Cleopatra or Romeo and Juliet. But Troilus and Cressida is really a story of infidelity: the unfaithfulness of Helen to Menelaus, which precipitates the Trojan war, and then the infidelity of Cressida to Troilus, which takes up the story's central narrative. And "romance" in the play is portrayed as being a pretentious kind of lust. The language of the play is thick with references to "whores" and "lechery," which seem to encompass all male-female relations. Cressida, the supposed romantic heroine, does not marry her beloved, as she would in a different kind of play—instead, she only sleeps with him, and their tryst is enabled by her uncle Pandarus, whose very name suggests "Pander," an Elizabethan term for a pimp. The central relationship is thus reduced to a prostitute, her procurer, and her eager lover—hardly the stuff of great traditional romance.