This chapter examines the emergence of a dream aesthetic in the orbit of Surrealism. While André Breton’s “Manifesto of Surrealism” (1924) and Louis Aragon’s “Wave of Dreams” (1924) point to the dream as a catalyst for a new kind of imaginative freedom, free of moral or aesthetic judgement, it was in Communicating Vessels (1932) that Breton brought the dream into direct correspondence with urban wandering and objective chance. In the process, Breton identified how the manifest content of his dreams drives an affective and sensorial attunement to people and places in the urban street, revealing the cathectic forces driving our aleatory engagement with the material world, and thereby assigning the dream a more critical, indeed, political cast. The second part of the chapter turns to the striking affinities between the dream and film uncovered by Surrealism, via the symbolic mapping of the Freudian dream in Buñuel and Dalí’s Un chien andalou (1929) and the melodramatic tension between symbolic objects and unconscious bodily movement in Maya Deren’s Meshes of the Afternoon (1943).