The Sleeping Cupid, by Italian painter Caravaggio is a masterpiece painted in 1608. Signs of an endocrine disease are hidden among the shadows of the painting. We decided to conduct a survey among endocrinologists practicing in Italy and asked them if they could identify a specific disease condition in Caravaggio's Sleeping Cupid. A total of 86 members from 2 Italian endocrine societies completed the survey: 67 from the Society of Endocrinology and 19 from the Society of Paediatric Endocrinology and Diabetology. Altogether 21 (24.4%) endocrinologists agreed the Sleeping Cupid was affected by hypopituitarism, 30 (34.9%) diagnosed rickets, 15 (17.4%) identified a SHOX gene defect, 16 (18.6%) did not agree on any of the suggested hypotheses, and 4 (4.6%) endocrinologists could not identify any disease. The perception looking at a painting can never be entirely similar to that of another person, even though a commonality of features may instead indicate the opposite. That must be the reason why, within a group of Italian endocrinologists who analyzed Caravaggio's Sleeping Cupid, pediatric endocrinologists (who see in their clinical practice exclusively children and teenagers) considered rickets as their first choice of diagnosis, whereas the majority of adult endocrinologists suggested hypopituitarism. In conclusion, as Walter Benjamin said "to arrive at the purity of the gaze is not difficult, it is impossible."