This paper seeks to reclaim irony as more than a way of humorously pointing out that the times we live in are out of joint or coming to an end, instead emphasizing its potential as a productive force and method in both educational thinking and teaching practice. By interrogating the educative potential of irony as method and humorous experience in the "Bildung"-oriented "Didaktik" tradition, we argue that irony can reveal the tensions and dilemmas of didactic posturing in order to facilitate a productive decentring and self-alienating critique of our anthropocentric predicament in education. It can be difficult to tease out the inherent distance between educational content and its substance in times where educators are caught between crowded curricula and strict testing regimes, but this irony is rarely lost on either pupils or teachers. Irony, we argue, is more than a constant fissure in the efforts to streamline ideas about what constitutes the most efficient didactic approaches. Instead, it could be used as a method to make educative processes attentive to what didactic posturing might be missing and how self-alienation might be a premise of education as formation of the self.