Much of Western philosophy has treated the ability to reason as both the defining feature of human nature and also the condition of knowledge. Even when philosophers attempt to expose reason’s finitude, the very form of argument simply bolsters the authority it seeks to constrain. Philosophy cannot fully displace rationality when it presupposes rigid standards of justification. But literature works differently: because it does not need to defend itself through argument, it can effectively reveal the limits of rationality. By examining the philosophies of Plato, Aristotle, Descartes, Hume, Kant, Foucault, Nietzsche, and Cavell together with the literary works Goethe’s Faust and Shelley’s Frankenstein, this article argues that literary work critiques rationality in ways philosophical discourse cannot.