A problem play by Creator/WilliamShakespeare, set during the TrojanWar-- Shakespeare used ''Literature/TheIliad'' as a reference. It has been variously described as a tragedy, a romance, and a tragicomedy; its oddly opposite but interwoven A and B plots make it difficult to classify.

The A plot, which provides the play name, is a romance-- Troilus, a brave warrior and prince of Troy, is desperately in love with Cressida. She returns his feelings, but is playing hard to get. Troilus uses Cressida's scatterbrained uncle, Pandarus, as a go-between; as a result, Pandarus spends most of the play singing Troilus' praises (and making bawdy jokes). Eventually, Troilus woos her and they consummate their relationship. However, Cressida's father, who defected to the Greeks, exchanges her for a Trojan soldier, and so the lovers are separated. Troilus asks her to be faithful, and gives her a love token (sleeve) to remember him by. He can't bear to be apart from her, though, so when everyone gathers for a duel between the two sides (see below), he goes to visit her. He discovers, however, that she has been seduced by Diomedes, a Greek warrior. In an extended scene, he and Ulysses watch secretly as she betrays him. Infuriated, Troilus decides to kill some Greeks, yells at Pandarus, and leaves the old man wondering what he did wrong.

The B plot is more serious, and concerns the war, borrowing heavily from Creator/{{Homer}}. Agamemnon, the Greek general, is upset that [[AchillesInHisTent Achilles is sulking in his tent]] and won't fight the Trojans. Ulysses and Nestor concoct a plan to get Achilles to return to battle: instead of using Achilles as their champion in a duel proposed by Hector of Troy, they send out strongman Ajax. This, they hope, will infuriate Achilles into fighting. Ajax boasts and beats up his extremely rude servant, Thersites, who snarks crassly at everyone. The duel falls through, and the next day, Hector kills Achilles' friend and lover, Patrocles. Mad with grief, Achilles hunts out Hector and kills him, dragging his body around the city.

An odd thing about ''Troilus and Cressida'' is that it doesn't end so much as stop. The drama between Troilus and Cressida, which is built up through the entire play, is never resolved; Troilus just storms off stage, and the play ends. Also, in defiance of Shakespeare's other tragedies, Troilus doesn't die at the end. The jarring juxtaposition between the political B plot and the romantic A plot is equally notable.
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!! ''Troilus and Cressida'' provides examples of:

* AchillesInHisTent: Literally.
* BadassGrandpa: Nestor is old as dirt, but said to be still as capable a soldier as he ever was.
* BerserkButton: Achilles does not take kindly to Patroclus' death.
* CassandraTruth: With the original Cassandra!
* CharacterExaggeration
* CharacterFilibuster: If Ulysses is speaking, there's a good chance it's going to be a two-page speech.
** Subverted when he's about to launch into another speech, and Cressida cuts him off after two lines of PurpleProse.
* CompositeCharacter: Other characters mention that Ajax is half Trojan, and that his mother was Priam's sister. In ''Literature/TheIliad,'' Ajax is simply a Greek warrior, but his half-brother Teucer (who also fights for the Greeks) is the son of Priam's sister who was taken prisoner during an earlier invasion of Troy.
* DarkerAndEdgier: Could be considered this for ''Literature/TheIliad.'' While the original is full to bursting with great Greek heroes doing great deeds, the play is a portrait of two armies mired in decadence, lechery, illness, violence, and corruption, where even young love turns sour and the final image is a syphilitic Pandarus promising to [[{{Squick}} "bequeath you my diseases."]]
* DoingInTheWizard: The gods do not appear.
* DumbMuscle: Ajax, whose lines tend to come in the form of short, uncomplicated prose exclamations. He would rather resort to violence than speech. Thersites mocks him mercilessly for it in their first scene.
-->'''Thersites:''' Thou sodden-witted lord, though hast no more brain than I have in mine elbows; an asinico may tutor thee. Thou scurvy-valiant ass, thou art here but to thrash Trojans, and thou art bought and sold among those of any wit like a barbarian slave.
* GetTheeToANunnery
* GoodIsDumb: Noted as one of Hector's character flaws.
* HonorBeforeReason: The reason they ultimately all meet a tragic end is because they refuse to do what is feasible, and instead seek to uphold their honor until death.
* HoYay: Thersites crassly accuses Patroclus of being a catamite, but the sparks ''really'' fly between Achilles and Hector, each of whom is curiously obsessed with [[DoubleEntendre seeing the other unarmed]].
* JerkassHasAPoint: Thersites may spout a whole lot of incendiary language, but he makes some fair observations about both sides and the war as a whole.
* LoveTriangle
* TheMatchmaker: Pandarus tries his best to be one between Troilus and Cressida.
* MoodWhiplash: The romantic plot between Troilus and Cressida, which is busting with sexual puns, and the serious story about war between the Greeks and Trojans.
* NameAndName
* NiceJobBreakingItHero: Word of advice, Hector: do ''not'', under any circumstances, murder the best friend and lover of the one man who a) has so far been content to sit out the entire war, greatly benefiting your side, and b) is the best warrior on the field and invulnerable save for his heel.
* NonActionSnarker: Thersites.
* {{Pungeonmaster}}: Pandarus, with sexual puns. Helen and Paris, too, come to think.
* QuestionableConsent: Cressida is a Trojan woman in a Greek war camp. [[SarcasmMode Yeah, she is completely in control of her situation]].
* {{Revenge}}: The reason Achilles finally leaves his tent.
* RoaringRampageOfRevenge: What happens once he does.
* SesquipedalianLoquaciousness: Ulysses. In his first speech (which is [[CharacterFilibuster 62 lines long]]), he uses "vizarded," "deracinate," and "oppugnancy." That's fancy even for Shakespeare.
* SexualExtortion: Related to QuestionableConsent, Diomedes basically gives Cressida the choice of being his woman or everyone's woman.
* ShoutOut: To Marlowe
* SlidingScaleOfIdealismVersusCynicism: ''Waaaaay'' on the cynical end. Arguably Shakespeare's most cynical play. Troilus just giving up, rather than dying heroically, is of course part of this.
* StillTheLeader: Agamemnon is determined to invoke his rank if the troops aren't going to obey him of their own volition, even if he is no longer respected.
* TheStoic: Ajax, who is parodied by Thersites in this aspect.
* WhatYouAreInTheDark: Even Hector behaves badly when no one is watching.
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