The era of digitisation is dominated by our reliance on visual representation. This has extended into health with the introduction of telemedicine. In response, clinicians are compelled to enhance their skills in remote observational medicine. However, the historical intersection of medicine and art reveals a rich tapestry of observation and representation. From Leonardo Da Vinci's sketches of the 'Vitruvian Man' to Albrecht Durer's 'Praying Hands,' anatomy students have often turned to art to deepen their understanding. Some disease, like Dürer's 15th-century engravings of Syphilis, are the obvious subject matter, serving as visual references for medical conditions. Yet, amidst celebrated artry, subtle medical nuances within hidden brushstrokes have often gone unnoticed until centuries later. Artistic renderings often knowingly capture objective signs of diseases that were once unfamiliar but are now recognizable to modern medical doctors. This presentation delves into the medical undercurrents of four renowned artworks: Rembrandt's 'Self Portrait,' Joseph Wright's 'An Experiment on a Bird in an Air Pump,' Michelangelo's 'Creation of Adam,' and Leonardo Da Vinci's 'Mona Lisa.' By examining these pieces through a medical lens, the focus is on highlighting signs indicative of diseases often unfamiliar in the eras of their creation. Additionally, the presentation aims to contextualize the sociocultural messages embedded in these artworks, unravelling layers of meaning that intertwine the worlds of art and medicine throughout history. As we accelerate deeper into the digital age, clinicians can examine the historical intersection between art and medicine to determine what visual cues constitutes sufficient information for a clinical diagnosis.