The first purpose of Art Education in public schools, articulated in the eighteenth century, was the ability to shape an imaginatively responsible, empathetic, democratic citizenry; this remains an aim for today, which is hard to achieve. This article explores the continuing tension between this original goal and other versions of Art Education, particularly Artistic Education, focusing on professional skills and techniques, and Aesthetic Education that focuses on appreciation of objects. After reviewing Friedrich Schiller's historic contribution to theorising aesthetics as empathy and as experienced through play, and Johan Pestalozzi's practical application in a first curriculum, the article demonstrates Schiller's influence on contemporary theorists Jacques Rancière and Gayatri Chakravorty Spivak who also insist that art must remain unproductive in order to defy cultural commodification. In their view, Art Education must be deviant to utility and retain an essential uselessness. A current case study demonstrates the difficulties in facilitating authentic democratic action within the utilitarian demands on today's schools. By developing wide-awakeness in students, spaces develop where silenced individuals might be heard. Art Education curricula should form the mindful habit of an informed citizenry that fashions an art of living by constructively re-imagining new possibilities of democratic community and empathetic understanding.