Two important movements leading the way toward a new approach to healthcare are narrative medicine and contemplative care. Despite considerable common ground between these two movements, they have existed largely parallel to each other, with different literatures, different histories, different sub-communities, and different practitioners. This article works toward integration of narrative medicine and contemplative care through a philosophical exploration of key similarities and differences between them. I start with an overview of their similar diagnosis of healthcare’s problems and then consider their related, but different, responses to these problems. Finally, I use the example of Margaret Edson’s Pulitzer Prize winning drama W;t to highlight how these issues can play out at the end of life.