Devoted to and inspired by the late Maxine Greene, a champion of education and advocator of the arts, this book recognizes the importance of Greene’s scholarship by revisiting her oeuvre in the context of the intellectual historicity that shaped its formation. As a scholar, Greene dialogued with philosophers, social theorists, writers, musicians, and artists. These conversations reveal the ways in which the arts, just like philosophy and science, allow for the facilitation of wide-awakeness, a term that is central to Greene’s pedagogy. Amidst contemporary trends of neoliberal, one-size-fits-all curriculum reforms in which the arts are typically squeezed out or pushed aside, Greene’s work reminds us that the social imagination is stunted without the arts. Artistic ways of knowing allow for people to see beyond their own worlds and beyond what is into other worlds of what was and what might be some day. This volume demonstrates Maxine Greene’s profound ability to illuminate the importance of the artistic world and the imaginary for development of the self in the world and for encouraging a wide-awakeness reflective of an emerging political awareness and a longing for a democratic world that is not yet. This book was originally published as a Special Issue of The Review of Education, Pedagogy and Cultural Studies.