In this chapter exploring the shadows of the unconscious we shall be in Venice: sometimes looking at Early Renaissance, and sometimes at twentieth century buildings, but always through a twentieth century Freudian lens – and specifically that offered by the British School psychoanalytic aesthetics of the analyst Melanie Klein (1882–1960) and art-writer Adrian Stokes (1902–72). The first part of this chapter asks: how can the psychoanalytic aesthetics of Klein and Stokes inform our understanding of architecture, shadow and the unconscious? Within these interpretative frameworks the second part explores shadow and the unconscious in the work and ideas of Aldo Rossi (1931–97) – focussing on his Teatro del Mondo, Venice.