This introduction presents an overview of key concepts discussed in the subsequent chapters of this book. The book outlines the intense urbanisation of recent times which has also brought into focus a range of anxieties, feelings of alienation, and a notable sense of unease; experiences that are often explicitly identified as effects and features of the city itself. Sigmund Freud the iconic pioneer of psychoanalysis, sought to map the psyche and its influences on a person's subjective experiences and behaviours in somewhat similar fashion to the topographer or urban geographer who surveys the physical and social terrains of the city. The Freudian uncanny is a curious combination of the familiar made strange, of repulsion and attraction. The urban uncanny denotes the slippage or mismatch between our expectations of the city, as the organised and familiar setting for citizens, for their work, habitation, and living, and the often surprising and unsettling experiences it can evoke within them.