The study sets out to examine how the concept of melancholy evolved from its usage in medical discourse to its usage in literature. How can we explain the fact that a term referring to a pathological condition close to madness and marked by extreme introversion and distraction should have become a key concept characterizing the expressive condition of the Romantic writer? Stripping away the modern usages of the term, the study adopts a rigorously historical perspective and analyzes a number of texts that cast a revealing light on the articulation of a philosophical and poetic purchase on the concept of melancholy and its pathological semantics.