This paper introduces an innovative curricular approach—the Health Humanities Portrait Approach —and its pedagogical tool—the Health Humanities Portrait. Both enable health professions learners to examine pressing social issues that shape, and are shaped by, experiences of health and illness. The Portrait Approach is grounded in a set of “critical portraiture” principles that foster humanities-driven analytical skills. The HHP’s architecture is distinctively framed around a pressing social theme and utilizes a first-person narrative and scholarship to explore how the dimensions of the (...) personal and the structural are mutually constituted. We argue that when creator-educators adopt the Portrait Approach and its critical portraiture principles to design and teach the HHP, they enable learners to become proficient in synthesizing and analyzing—with both depth and breadth—the human and social dimensions of patients’ lives. This inventive curricular intervention provides a needed contribution to health professions education in that it utilizes health humanities methodologies to elucidate the multiple aspects of health, illness, disability, and healthcare. (shrink)