This praxis-based book explores how an improvisational, creative and embodied practice such as the derive works to defamiliarise our experience of the late modern built environment, fostering new insight into routinised cultural behaviours. In addition to detailing the key contexts of modernity, this book includes case studies on the work of Viktor Shklovsky, Craig Raine, Georges Perec, plus rare scholarly attention to the postcards of Jim Henson's Uncle Traveling Matt. Tertiary students and early career researchers in the humanities, particularly cultural theory and the creative arts, will read about the work of internationally recognised artists who have responded creatively to the urban landscape in view of its habituation under advanced capitalism. The research aims to provide sufficient detail for the reader to recognise a range of cultural conditions pertaining to the historical period that frames contemporary quotidian experience and that, in turn, informs a wide range of reflexive, creative practices. The book's hybridity (complimenting a traditional scholarly style with auto-ethnographic and journalistic writing) offers the reader an authorial honesty, transparency and humanity in its intellectual, practical, and emotional negotiation of psychogeographic ideas.