In the Italian Cinquecento medical and art-theoretical discourses intersect in the semantics of capriccio. The innovative and transgressive potential of capriccio was simultaneously denounced as pathological and as an existential risk. Hans Joachim Dethlefs reconstructs the history of the term capriccio within the context of the early modern re-evaluation of the imagination. The study brings together art history, linguistics, and the history of knowledge, revealing the extent to which notions of creativity were marked by ambivalence in this period. In doing so, it sheds light on how modern ideas of invention, deviation, and individuality first emerged – far beyond the confines of art history.