Creative arts have been increasingly implemented in medical education. This study investigated the use of interactive theater and role play with professional actors in teaching breaking bad news to medical students. The objectives were to explore the contexts, approaches, experiences, and reactions in giving and receiving bad news. Second-year medical students participated in a required educational session that utilized interactive theater which helps students learn about the issues of breaking bad news to a patient with cancer. Following the interactive theater piece, professional actors provided students role play experiences in small groups with breaking bad news. Anonymous evaluation surveys were given out to all second-year medical students at the conclusion of the breaking bad news session. Surveys contained quantitative and qualitative responses. Three years of evaluations were analyzed. A total of 451 (88 %) students completed the evaluations. Comments were thematically analyzed. Ninety-four percent agreed that the theater piece prompted reflection on patient-provider communications, and 89 % agreed that it stimulated discussion on complex issues with breaking bad news. The two most common themes in student comments concerned the importance of realism in the theater piece, and the value of experiencing multiple perspectives. Use of professional actors during the role play exercises enhances the realism and pushed the students out of their own "comfort zones" in ways that may more closely approximate real life clinical situations. Interactive theater can be a potentially powerful tool to teach breaking bad news during medical school.