For Richard Rorty as well as Stanley Cavell, the realm of the literary carries particular educational force. Literature holds the potential to lead the insensitive and the superficial towards the responsive and the detailed. Literature prompts an interrogation of everyday expressions and the felt meanings we decide to invest or not to invest within them. In this paper, we draw on the work of Rorty and Cavell to highlight the significance of literature for moral education. We argue that both philosophers are committed to the transformative power of literature even if this transformation is conceived in very different ways. Broadening our scope from the Anglo-American to the European tradition, we propose in the paper's final section that Rorty and Cavell's readings of Derrida can usefully illuminate the fundamental philosophical differences between them.