Planners are asked to deal with an aphoristically constructed urban reality, while being practically reluctant towards the ‘un-programmable’ real life of each citizen.However, the conceptions and perceptions of the Real (realities) have changed during the timespan. What follows is an anthology of the three pivotal mutations, which are linked to certain ‘structures of feeling’ (a term used by Raymond Williams): modern, postmodern and metamodern, and aspires to detect their inexhaustible mark on urban planning (conception of urban reality) and urban living (experience of the urban Real), as featured in three representative films: Lang’s Metropolis (1927), Burton’s Batman Returns (1991) and Nolan’s Inception (2010).