The essay explores how Simon Critchley’s critique of philosophy and understanding of tragedy might affect bioethics and health-care practice. What I playfully call the Critchley Doctrine begins with a rejection of philosophy’s aspiration to a non-contradictory life and its premise that humans act on rational deliberation. This rejection opens us to a recognition of the uncontainable that is expressed in tragedy, and that speaks to what is inexplicable about the suffering of illness. Critchley advocates an ethics of heteronomy or hetero-affectivity rather than autonomy, but his version is distinguished by its recognition of how crushing the demands of the other can be. Tragedy and humor offer what he calls aesthetic reparation. A tragic medicine balances grieving with humor and seeks above all honesty in communication.