Stoic virtue relies on the judgment of internal impressions. This aesthetic and ethical process echoes Shakespeare’s theatrical art, which frequently focuses on its own artifice and capacity to affect reality. While early modern dramatists frequently mocked Stoicism as stuffy and impractical, a closer look at fundamental texts by Seneca, Epictetus, and Marcus Aurelius reveals their interest not in attaining perfect sagacity but instead in the day-to-day reality of attempting to live better. Stoicism, thought of in this way, becomes what Pierre Hadot calls “a way of life,” and allows us to read Shakespeare’s drama more charitably as a mode of philosophical exercise. This chapter surveys Stoic understandings of virtue before turning to A Midsummer Night’s Dream to examine how the play’s testing the imaginative powers of theatricality mirrors the Stoic’s internal processes of judgment. Drawing on key Stoic texts as well as the 1581 translation of Seneca’s Hippolytus, a source for Midsummer, I propose that the play reveals the potential for imaginative impressions to become mere fantasy — but also admits to their power over our consciousness. While this may appear anti-Stoic, Midsummer in fact mounts its apology for the imagination by practicing mercy, a key Stoic virtue.