In this article Karl Hostetler portrays teachers as tragic ironists whose existence is prone to "playful disruptions of the soul," when the meaning and value of ideas pertinent to teaching--including "teaching" itself--become puzzling, prompting a reassessment and reinvigoration of those ideas. In developing his concept of tragic irony, Hostetler draws particularly on Jonathan Lear's "A Case for Irony" and the Greek tragedies "Oedipus Tyrannus" and "Medea." According to Lear, the aim of irony is "to inject a certain form of not-knowing into polis life." Relatedly, Hostetler observes, a frequent theme in classical Greek tragedy is the misery that can result from purporting to "know." Tragedy and irony, he argues, can be particularly powerful and unsettling avenues for introducing uncertainty. He further contends that teachers as tragic ironists maintain a measure of uncertainty about their craft, not only recognizing that they do not know everything, but sometimes questioning whether they know anything. In a culture that tends to valorize certainty, Hostetler concludes, this is an essential attitude in the practice of and discourse about education.