By virtue of his "Essays" Montaigne is rightly regarded not only as a radically modern philosopher but also as a transformative educational innovator. He confronted the extent to which pedantry and acculturation can justify cruelty by developing a conception of liberal arts education as the arts of liberation, and at the core of this education he placed the practice of essaying. This article argues that in easing us into essaying practices Montaigne qua educator makes reflexive use of three specific modes of didactic humor: incongruous comparison, subversive superiority, and leveling embodiment. Humor thus emerges as a cognitive disposition and communicative mode especially appropriate to the pedagogical engagement with difference today.