Since the 1950s, play has become part of arts education, and nowadays “doing” or creating something by playing is becoming more and more prominent in artistic training, but also in education in general and in (postschool) professional trainings. Based on the historical insights of Johan Huizinga (1949), the author analyzes the role of play for arts education. Especially Huizinga’s theories of play as “pre-cultural” and going beyond the ethics of good and bad open an interesting perspective. How does “play” play a role in the processes of socialization, qualification, and subjectification in the post-Bologna educational realm in which measuring (assessments, audits, contact hours, competences) has become an obsession? The author argues that the spirit of the avant-garde artist can stimulate the process of subjectification and of civil action. This is a “dismeasuring” potency of art education that needs to be cultivated to prepare students for a constantly changing future in which civil society will play a primordial role. It is a matter of preparing them for what one cannot prepare for.