How is it that our enjoyment of tragic theater is enhanced as the pain, fear, and pity it evokes become more intense? Does just the distancing mechanism of ‘make-believe’ and ‘mimesis’ explain why normal, nice people enjoy watching others suffer on stage or on the screen? Aristotle has traditionally been read as explaining away the puzzle of tragic pleasure in terms of a cathartic cleansing of the emotions through witnessing the play of complex feelings inside the spectator when the theatrical narrative is acted out. But such an interpretation of Aristotelian katharsis appears to work by a weakening of the intensity of the emotions, particularly as we relate to imagined others. In contrast, the eleventh-century Kashmir-Shaiva philosopher Abhinavagupta finds the solution of the puzzle within the magic of heart-sharing through aesthetically transformed emotions themselves. The audience of a tragedy no longer needs to be passive, disinterested witnesses who have elided the alterity of others. Ours is an exercise in comparative aesthetics of theater by imagining a debate between Aristotle and Abhinavagupta on the puzzle of the pleasures of a tragedy. Along the way, it challenges standard readings of both thinkers, considers and responds to serious objections to these theories, and offers insights into how the experience of theater provides important resources for moral transformation.