In this article, the author challenges the recurrent theory-practice divide in art teacher preparation and its splintering implications for sustaining certain pedagogical practices in K-12 schools. Specifically, the author focuses on the pedagogical practice of emergent curriculum and the derivative curricular cycle of listening, observing, reflecting, discussing, and responding to children. This article addresses the theory-practice divide by problematizing and challenging the emergent curriculum process with preservice art educators. The author found that collaborating in and through a Drawing Club helped reaffirm the importance of providing for and nurturing practical opportunities for troubleshooting what is valued theoretically but not easily translated into best practices within art teacher preservice education programs.