Recent decades have witnessed the rebranding of STEM-oriented disciplines—including computing, technology, and, of course, medicine—as compatible with the knowledge, skills, and aptitudes conventionally associated with the arts and humanities. Meanwhile, debates concerning the value of the arts and humanities often wrestle with the implications of such appeals to use, utility, and application. This chapter examines the longstanding issue of the “application” of arts and humanities in health and health-related settings, with particular emphasis on the practice of “empathy training.” Drawing from the critical literature, direct experience as a researcher and narrative training facilitator, and contemporary Anglophone creative writing and film, Andrea Charise tracks how the uptake of empathy training in health environments may in fact be aligned with an increasingly neoliberalized culture of health care across North America and Europe. Close reading of provocative examples—including Ken Loach’s Palme D’Or-winning I, Daniel Blake (2016)—illustrate the consequences of artificially separating theory and application, particularly concerning matters of health in the twenty-first-century context of neoliberalism and the austerity climate it has engendered.