Many medical schools have incorporated experiences with representational or figurative art into the curriculum in an effort to improve learners' powers of observation, visual diagnostic skills, and pattern recognition skills or to enhance communication skills, foster teamwork, and/or improve empathy. The Keck School of Medicine of the University of Southern California has partnered with Los Angeles' Museum of Contemporary Art to design an educational experience with the goal of honing students' abilities to observe, describe, and interpret complex information. The authors discovered that through a constructivist approach to viewing and discussing nonrepresentational, contemporary art, students were able not only to apply their observational and interpretive skills in a safe, nonclinical setting but also to accept the facts that ambiguity is inherent to art, life, and clinical experience and that there can be more than one answer to many questions. This intervention, entailing extensive guided inquiry, collaborative thinking, and process work, has allowed students and faculty to reflect on the parallel processes at work in clinical practice and art interpretation. In patient encounters, physicians (and physicians-in-training) begin with attention and observation, continue with multiple interpretations of that which they observe, move to sorting through often ambiguous evidence, proceed to collaboration within a community of observers, and finally move to consensus and direction for action. In the worlds of both art and medicine, individuals imagine experiences beyond their own and test hypotheses by integrating their own prior knowledge and intuition and by comparing their evidence with that of others.