Freud was the first to apply psychoanalysis to art, choosing for his subject the life and work of Leonardo da Vinci. Observing Leonardo's partly fused image of the Virgin and St. Anne, he inferred that the artist had depicted his two mothers, his biological mother and his stepmother. This very early analytic discourse on parent loss and adoption changed the course of the interpretation of art. Freud explored the psychology of art, the artist, and aesthetic appreciation. Confronting the age-old enigma of the Mona Lisa, he proposed a daring solution to the riddle of the sphinxlike smile of this icon of art. His paper prefigures concepts of narcissism, homosexuality, parenting, and sublimation. Lacking modern methodology and theory, Freud's pioneering insights overshadow his naive errors. In this fledgling inquiry, based on a childhood screen memory and limited knowledge of Leonardo's artistic and scientific contributions, Freud identified with this Renaissance genius in his own self-analytic and creative endeavor.