For Shakespeare, the Trojan War arguably functions as the archetypal scene of war, as, aside from Troilus and Cressida, his texts frequently reference it. The play endured critical neglect for centuries, due partly to its ambiguity of genre and misunderstood aesthetics. This chapter employs Hugh Grady’s theorizing on both presentism and aesthetics to demonstrate that Shakespeare’s two texts discussing Troy at greatest length outside of Troilus and Cressida illuminate the presentism of that play. In these texts, The Rape of Lucrece and Hamlet, the Trojan War becomes the subject of ekphrasis, with each title character lingering over an artistic rendering of it while pondering a personal tragedy. Through interaction with a Trojan War painting as she grieves her rape, Lucrece ‘time-travels’ back to its moments and ‘artistic-mode-travels’ into it, as though she were a figure among those represented. Hamlet also imaginatively enters Troy, through the speech on Hecuba recited in part by himself and continued by an actor. While Lucrece and Hamlet live in the artistic past, they join Troilus and Cressida’s main characters in an aesthetic ‘eternal present’, the territory of presentism.