© 2015 Shapiro et al. Medical school curricula, although traditionally and historically dominated by science, have generally accepted, appreciated, and welcomed the inclusion of literature over the past several decades. Recent concerns about medical professional formation have led to discussions about the specific role and contribution of literature and stories. In this article, we demonstrate how professionalism and the study of literature can be brought into relationship through critical and interrogative interactions based in the literary skill of close reading. Literature in medicine can question the meaning of "professionalism" itself (as well as its virtues), thereby resisting standardization in favor of diversity method and of outcome. Literature can also actively engage learners with questions about the human condition, providing a larger context within which to consider professional identity formation. Our fundamental contention is that, within a medical education framework, literature is highly suited to assist learners in questioning conventional thinking and assumptions about various dimensions of professionalism.