This article aims to challenge and expand notions of health, health care and health promotion, particularly in relation to smoking, via a consideration of the autobiographical literary work of the English playwright, Simon Gray. Gray died in 2008, having written a series of reflective autobiographical books, The Smoking Diaries. Gray was a lifelong smoker, perpetually trying to give up his habit. This article introduces Gray's diaries and their reflections on life, death, health care and smoking. It then enquires what can be learned about contemporary health care practices and assumptions from Gray's work. Finally, it reflects on the limits of views of health and health promotion when considered in the light of a fully lived life. In the life under consideration, health care risks are very differently understood to those prevalent in the medical community. Literary approaches to thinking about smoking are thus seen to place health and health care in broader, richer, and less instrumental perspectives than those that are common amongst contemporary health professionals and institutions.