This essay elaborates on the dialectics of practice and play in Walter Benjamin’s pedagogical writings. Arguing that his earlier politics of “pure means” is still operative in his later materialist pedagogy of proletarian purposiveness, the essay follows Benjamin’s project of undoing bourgeois pedagogy. Departing from the Kantian concept of pedagogy, already the younger Benjamin criticizes humanist teleologies of child education. Unraveling the aporias of bourgeois pedagogy, he takes hierarchical oppositions, such as civilization and nature, mind and body, teacher and student, mastery and servitude, intentional continuity and unintentional deviation, as his starting point to perform a dialectical reversal at the heart of these oppositions. This critico-destructive move makes room for new pedagogical constructions beyond the confines of bourgeois pedagogy. Drawing on his later anthropological-materialist concepts of gesture, practice, and mimesis, the essay concludes that, rather than developing completely new pedagogical concepts or setting new utopian goals, Benjamin radicalizes the impoverished life conditions of capitalist modernity and reduces pedagogy to a mimetic practice, which, nevertheless, demonstrates a radically new way of practicing.