Psychogeography came to exist because you can live in a city and still go searching for it. Nearly seventy-five years ago, Guy Debord and the Situationists defined psychogeography as “the study of the precise laws and specific effects of the geographical environment, whether consciously organized or not, on the emotions and behavior of individuals.” It was an avant-garde practice, notably employing dérive (drift), whose goal was to liberate city-dwellers from the forms of alienation imposed by urban planning and spectacle. Today, the term “psychogeography” continues to pop up in contemporary literature and art, where fieldwork-inspired essays, art installations, and performances have taken particular interest in the question of everyday spaces and rhythms in the city. This chapter traces the roots of this radical, topo-analytical tradition from the nineteenth-century flâneur, up through contemporary writers, filmmakers, and artists such as Iain Sinclair, Philippe Vasset, Patrick Keiller, and Sophie Calle. Psychogeography remains appealing today because of its intransigent, topophilic wager that alienation from one’s built environment can be dispelled if only one can re-envision or recreate one’s relationship to space and place.