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This essay is an exercise in imaginative historiography. Its purpose is to modify the boundaries between sociology, social work, and literature that have become impediments to the pursuit of socially responsible scholarship; its goal is to create an analogue in the past for a field that many revisionists wish to create in the present – a field of cultural inquiry in which knowledge is considered both cognitive and emotional, methods are imaginative, and results are meant to improve human relations. In the past I posit as a “working hypothesis” (in Mead’s sense of the term) for this field, I bring together figures, specifically Jane Addams and the nineteenth-century playwright Joanna Baillie, whose contributions to sociology and literature are being separately but not jointly recovered. I examine three key similarities that make Addams and Baillie kindred spirits: they cultivated sympathy as a way of knowing and acting, and made it the basis for social change; they preferred situational problem-solving to theory-building; they used drama for value inquiry and morality construction. Throughout, I also allude to affinities with the thought of Mead, affinities that are important for avoiding gender essentialism in this argument. I illustrate the combined use of problem-solving, sympathy and drama by linking Baillie’s plays on criminality with Addams’s and Mead’s efforts at criminal justice reform and with present-day efforts to move from an ethics of justice to an ethics of care. By bringing Baillie to Hull-House and considering how she might have contributed to the work of Addams, Mead, and their associates, I construct a precedent for transdisciplinary cultural inquiry.