Although much discussion and research has taken place surrounding the centrality of story and illness narratives in the medical and health humanities and humanistic patient care, less attention has been given to the role of the imagination within clinical encounters, complex medical decision making, and medical education. This paper reflects on how the imaginations of students and clinicians can be trained by engaging concrete practices held within the humanities, the arts, and embodied artistic research. Examples are given of how the imagination is a skill that can be developed to counter the dehumanization of clinical care brought about through technological and economic transformations of health care, and pending advances in artificial intelligence. Conceptual frameworks from actor–network theory, cognitive science, mindfulness, and phenomenology advance the centrality of the imagination for the recovery of an embodied practice of medicine that attends to the structural foundations/social determinants of health and biopolitical power. Developing imaginative capacity and articulate bodies that are able to be affected is needed to discern the nuanced lived experiences of patients, diminish clinician burnout and moral injury, and shape new systems of care practice and delivery.