Troilus and Cressida is set during the later years of the Trojan War, faithfully following the plotline of the Iliad from Achilles' refusal to participate in battle to Hector's death.

Immortalized in Greek mythology and Homer's Iliad, the war occurs because a Trojan prince, Paris, has stolen the beautiful Helen from her husband, King Menelaus of Sparta, and carries her home to Troy with him.

As they converse, several Trojan lords pass by them returning from battle, including Antenor, Aeneas, Hector, and Paris; Pandarus praises each one, but tells his niece that none of them can match Troilus.

He asks why they seem so glum and downcast for although their seven-year siege of Troy has met little success so far, they should welcome the adversity that the long war represents, since only in difficult times can greatness emerge.

Instead of being united, they are divided into factions: Achilles refuses to fight, and instead stays in his tent while Patroclus ridicules the Greek commanders; others, like Ajax and his foul-mouthed slave Thersites, follow this example, and so the entire army is corrupted.

Hector, supported by his brother Helenus, argues eloquently that while the theft of Helen may have been a brave act, she cannot be worth the great and bloody price they are paying to keep her.

They see the Greek commanders Agamemnon, Ulysses, Nestor, and Diomedes approaching, accompanied by Ajax, and Achilles quickly retires to his tent.

Paris and Helen ask where Troilus will be dining, and Pandarus refuses to tell him but they both guess that he will be in pursuit of Cressida, and they make bawdy jokes about it as they depart to greet the returning warriors.

On Ulysses's advice, the Greek commanders then file past Achilles's tent, and scorn the proud warrior, ignoring his greetings and making him uneasy.

Aeneas goes to fetch Cressida, remarking that this exchange will deal a heavy blow to Troilus; Paris concurs, but says regretfully that they have no choice: "the bitter disposition of the time will have it so".

The letter is from the Trojan princess, Polyxena, whom Achilles loves, and it begs him not to fight the next day; he tells Patroclus sadly that he must obey her wishes.

With Thersites's profanity and Troilus's shock providing a counterpoint, Diomedes woos Cressida, who behaves reluctantly but coyly toward his advances, fending him off for a time but never allowing him to leave.

Cassandra leads Priam in, and the old king pleads with his son not to fight, saying that he too feels foreboding about this day, but Hector refuses to listen and goes out to the battlefield.

[8] Yet the deep sense of Troilus and Cressida, according to Anthony B. Dawson, lies exactly in its perplexity: "It is still full of puzzles, but that fact has been recognized as a virtue rather than a defect – its difficulties are generative, its obstacles fruitful".

[9] Jonathan Bate is one of many modern authors who regard the play as a satire, deliberately undermining the heroic and romantic style of George Chapman's new and popular translation of Homer.

He instances the cynical attitude of Pandarus towards the overnight tryst arranged between the lovers, and the weak, "feminine" language of the supposedly valiant warriors.

Literary critic and scholar Joyce Carol Oates wrote that in reality these shifts complemented the values Shakespeare questioned in the play: love, honour, and hierarchy.

Oates considered the play a new kind of contemporary tragedy – a grand existential statement: Troilus and Cressida, that most vexing and ambiguous of Shakespeare's plays, strikes the modern reader as a contemporary document – its investigation of numerous infidelities, its criticism of tragic pretensions, above all, its implicit debate between what is essential in human life and what is only existential are themes of the twentieth century.

[15] For his part, Benoît extended stories from Dictys Cretensis and Dares Phrygius from the late Roman period, which entwine around the Iliad material, with his own romantic sub-plot.

Publication followed in 1609; the stationers Richard Bonian and Henry Walley re-registered the play on 28 January 1609, and later that year issued the first quarto, but in two "states".

[21] Some commentators (like Georg Brandes, the Danish Shakespeare scholar of the late 19th century) have attempted to reconcile these contradictory claims by arguing that the play was composed originally around 1600–1602, but heavily revised, possibly by another hand, shortly before its 1609 printing.

[22] The play is noteworthy for its bitter and caustic nature, similar to the works that Shakespeare was writing in the 1605–1608 period, King Lear, Coriolanus, and Timon of Athens.

The confusion is compounded by the fact that in the original pressing of the First Folio, the play's pages are unnumbered, the title is not included in the Table of Contents, and it appears to have been squeezed between the histories and the tragedies.

Taking into account the fact that the second public printing of the quarto edition (1609) dropped the first's familiar testimonial "as acted by the King's Majesty's Servant's at the Globe", it has been suggested that work was performed only once.

In 1679 John Dryden "new modell'd the plot", re-ordered the scenes, and presented the work as The Truth Found Too Late at the Duke's Theatre, London.

[24] In 1795 John Philip Kemble prepared an acting version which emphasised the warriors and sidelined Cressida, but he abandoned the production before opening night.

When the play had been chosen for performance during the twentieth century, while being out of fashion before, it showed that there was something about its themes and subject matter which was familiar in the mindset of the contemporary audience.

For example: John Barton, during his preparation for the 1968 Royal Shakespeare Company production, saw the parallels between the prolonged war in Viet Nam and the stalemated siege of Troy as offering a way into the script, commenting that: "The basic situation […] is ludicrous, but also an insoluble impasse where both sides are inexorably committed.".

[19] Translations of the Iliad were made in Greek, Latin and French in Elizabethan England; moreover, Shakespeare's contemporary George Chapman also prepared an English version.

In his drama, Shakespeare does not simply intensify these negative tendencies, but links and superimposes contradictory characterizations in order to make his characters interesting and accessible to his audience.