In this essay, I look back at some of the earliest attempts by the first generation of literature-and-medicine scholars to answer the question: Why teach literature and medicine? Reviewing the development of the field in its early years, I examine statements by practitioners to see whether their answers have held up over time and to consider how the rationales they articulated have expanded or changed in the following years and why. Greater emphasis on literary criticism, narrative ethics, narrative theory, and reflective writing has influenced current work in the field in ways that could not have been foreseen in the 1970s. The extraordinary growth of interest and work in the field nationally and, especially since 1996, internationally has included practitioners in many additional areas such as disability studies, film studies, therapeutic writing, and trauma studies. Along with the emergence of narrative medicine, this diverse community of scholars and practitioners-affiliated more through their use of narrative methodologies than the teaching of literature-makes the perennial challenge of evaluation and assessment even more complicated.