The practices of artists and the field of artistic production is an iterative space--a rapidly evolving network of ideas and dialogic strategies, as well as collaborative and interdisciplinary practices. Artists function at the intersection of many disciplines as researchers, activists, and problem solvers. These practices provide an imperative to teach about the transdisciplinary potential of the artistic process and the changing scope of artistic work. After 7 years of working with educators participating in the ART21 Educators community, the authors began to identify specific alignments between what artists do and the innovations and aspirations of exceptional teachers. This article highlights specific strategies that connect the work of artists and educators across subject areas and grade levels sharing actual examples of classroom practice. While other artists and educators have articulated the importance of looking to contemporary art and artistic practices (Gude 2004, 2007, 2009; Marshall, 2010), the authors focus on the connection to lived experience and teaching models steeped in the realities of today's classrooms.