Medicine, art and assessment - unhappy bedfellows or a marriage made in heaven? The question of how best to evaluate arts- based medical education initiatives is thorny. Medicine’s legacy of measurement struggles, with calls for ‘rigorous evaluation’, suggesting preference for a numerical metric and that objectivity is somehow attainable. It is somewhat ironic therefore to reflect on the growing use of the term ‘the art of assessment’, a term used to capture the complexity of the current assessment of medical students. Diversity of methodologies are promoted to ensure breadth and to capture the range of competencies that constitute ‘being a doctor’. That one might apply the metaphor in its literal sense, and use art to assess is likely to generate surprise. Yet that is what we did. This is the story of how we did it, why we did it and how it worked.