Medical Humanities may be broadly conceptualized as a discipline wherein medicine and its specialties intersect with those of the humanities and social sciences. As such it is a hybrid area of study where the impact of disease and healing science on culture is assessed and expressed in the particular language of the disciplines concerned with the human experience. However, as much as at first sight this definition appears to be clear, it does not reflect how the interaction of medicine with the humanities has evolved to become a separate field of study. In this publication we have explored, through the analysis of a group of selected multidisciplinary essays, the dynamics of this process. The essays predominantly address the interaction of literature, philosophy, art, art history, ethics, and education with medicine and its specialties from the classical period to the present. Particular attention has been given to the Medieval, Early Modern, and Enlightenment periods. To avoid a rigid compartmentalization of the book based on individual fields of study we opted for a fluid division into multidisciplinary sections, reflective of the complex interactions of the included works with medicine.