Troilus and Cressida

One of the lesser known tragedies of Shakespeare, this play is set in the time of the Trojan war. Essentially, the plot focusses on the Trojan prince, Troilus' love for Cressida the daughter of a Trojan priest who has switched to the Greek side.
The unusual element of this play is the wavering between comic humour that seems to mock the aspect of tragedy, as seen in the character of Achilles' the Greek soldier whose straying from combat is due to his petulant nature. This is contrasted by the ultimate tragedy of the play, the death of the mighty warrior Hector and the dissolution of Troilus and Cressida's love.
The play overall has a distinctly modern feel which is jarring compared to the ancient and classical setting.
However, the play bears all the hallmarks of a Shakespearean play, Priam, king of Troy is hesitant to continue the war due to his dispirited soldiers, comparable to Hamlet's hesitation that ultimately leads to tragedy. There is comic relief provided by Ajax, the bumbling, yet fearsome warrior as he is coaxed into fighting Hector. And of course, the tragic love story of Troilus and Cressida, which culminates in her rejection of Troilus for the Greek prince Diomedes.
The wavering subject matter, between the Trojan war and the main characters love affair may seem frustrating to an audience accustomed to more conventional and straightforward plots, yet this is precisely what gives this play its modern feel, the intimacy of Troilus' failed love is contrasted with the bloodshed of the Trojan war.