Theatre scholar Jan Kott in the 1960s called Troilus and Cressida one of the biggest problem plays by Shakespeare. Although presented as tragedy, none of the protagonists die; cynicism of the text is overwhelming. Fascination with the Trojan War that was accompanying European civilisation throughout the medieval times gets new meaning of non-heroism in this treatment by Shakespeare.

Although the character of Cressida did not appear until 1190 AD, in the French romance of the Troy War, and two hundred years later in Chaucer who served as Shakespeare main source, the play still has an astoundingly modern sound.