The purpose of this study is to explore how representational paintings of radiology encounters with patients may impact medical students' understanding and impression of both radiologists and the radiology profession. Participants included third year medical students at a single institution rotating through a one-week radiology elective. Three works of art were analyzed using the validated Visual Thinking Strategies technique. Data collected included a postsession questionnaire and transcriptions of audio-recorded sessions. Data analysis involved both qualitative and quantitative methodology. Fifty students participated; all participants completed the postsession questionnaire and 10 participated in the audio recorded sessions. Total 82% found the experience "very enjoyable" and 86% agreed that the paintings positively affected their understanding of how radiologists provide care to patients; 96% would recommend this session to others. Exploring representational paintings of radiology encounters seemed to influence perception and understanding of radiology with students reporting "light bulb moments;" create a dissonance between the student experience and the experience depicted in the paintings; and address gaps in content specific knowledge. The findings of this study suggest that analyzing paintings depicting radiology encounters with patients can challenge negative stereotypes that medical students have of the radiology profession and radiologists. This arts-based learning module employing a learning strategy such as Visual Thinking Strategies, should be considered by the radiology profession as a strategy to positively inform and educate trainees about the specialty.