AbstractAstute observation is a fundamental skill in medical care because not only it is crucial for the detection of patients' emotions (which is a prerequisite for empathy) but also it can often yield diagnoses at first sight. The Germans call this technique “augenblickdiagnose,” and indeed, gestalt diagnosis together with systematic review is used by dysmorphologists to identify syndromes. Artists have traditionally excelled at skilled observation since it is necessary for realistic portrayal of the human form. Thus, not surprisingly, they have also often depicted syndromes and defects in artworks, decades or even centuries earlier than their medical counterparts' description. Although physicians should avoid overdiagnosing or medicalizing what may be ethnic variations, personality traits, or just artistic style, this commentary will review how syndromes and various physical differences have been represented in artworks. It will then provide practical tips on how to become better observers. The historical relationship between artists and physicians provides context for our mutual diagnostic and interpretative pursuits.