The ways in which today's psychoanalysts approach art closely follow the avenues opened by Freud a hundred years ago. Drawing mainly on Freud's studies on Jensen's Gradiva (1907) and on Leonardo da Vinci (1910a), the author examines the main paradigms he used in discussing artistic activity, including his doubts and hesitations. Present-day approaches to art are then examined via a discussion of the advantages and pitfalls of psychobiography, of the case study, and of textual approaches. The author makes a case for the type of interdisciplinary dialogue in which the goal is to establish a cross-fertilization between psychoanalysis and other fields of knowledge while striving to avoid hypersaturation of a work of art in order to foster expansion of the mind.