Increasingly, undergraduate and graduate programs in medical humanities are exploring the ability of the arts to elucidate the human condition as it relates to patient care. At the University of California, Davis, students and faculty from both the Department of Medicine and English Literature have convened for informal readings of scenes from dramatic works. This paper discusses the use of excerpts from Eugene O’Neill’s Long Day’s Journey into Night and Berry Barta’s Journey into That Good Night in a medical education setting. Medical students participated in staged readings of these plays, which were filmed and then screened for a group of 30 medical students in order to elicit discussion. Topics included how individuals deal with illness differently and how prospective physicians could address similar clinical scenarios. Medical students contributed to a fluid, evolving project in which they oftentimes struggled to play a character but appreciated the opportunity to do so and to observe their peers in a similar fashion. Future plans for the project include further staged readings and presentations to larger groups of students with the intent of incorporating these activities into the medical school curriculum.