The decades-long surge of artistic interest in social practice finds a potential confluence in the recent rise of moral character as an object of psychological study, with both ideas filtering downstream into contemporary arts education philosophy and practices. Although much has been written about the social turn in the arts and the cultivation of character in education, few investigators have analyzed the relationship between them. This conceptual essay contributes to a possible convergence by examining the tensions and opportunities inherent in the integration of experimental art-making with the traditions of social science and moral theory. Its purpose is to take a personality-based approach to socially engaged art-making: to understand why some artists engage in social practice and the implications for arts education. This inquiry draws from a series of public interviews that examine the works and values, thoughts and feelings, practices and perspectives of contemporary artists working in higher education.