There is no inherent relationship between "play" and "difference." However, in William Doll's curriculum and pedagogical theory and practice, "play" and "difference" take on quite different meanings, and his playful engagement with difference as a teacher and as a scholar has opened up a new landscape in education. The key to opening students and teachers to this surprise is playful engagement with intellectual difference. The Derridian notion of "learning" requires learning something other and different that cannot be fully mastered. The transactional nature of play between and among students, texts, teachers, and situations requires participants to lose themselves in the process of engagement in a to-and-fro movement of making sense to generate new meanings. In short, William Doll's curriculum theory and practice challenge taken-for-granted assumptions and to rethink the meanings of play, engagement, and difference in keeping knowledge alive and enabling personal growth and communal inquiry.