The Japanese media have featured articles on the escalation of youth crime and discontent, as well as the many forms of corruption that teenagers are exposed to in transformed downtown Tokyo. The 2002 Naoki literary prize was awarded to a book that reacts to both urban development and the problems facing Tokyo adolescents - Ira Ishida's 4-Teen (2002). Ishida shows the effects of Tokyo's transformations on teenage social norms and uses descriptions of urban places to reveal contradictions embedded in these roles. This article examines the context of 4-Teen's publication and the awarding of the Naoki Prize and explores how stories that mix fiction and historical experience provide new ways of viewing the changes in Tokyo.