This thesis examines the figure of the wandering adolescent, prominently visible in Japanese television anime and videogames produced from 1995 to the present. Japan in the 1990s and at the millennium experienced intense economic and social change, as the collapse of the 'bubble' economy of the 1980s resulted in a financial recession from which the country has yet to recover. At the close of the decade, the national experience was characterised in media descriptions of malaise and disenfranchisement, and the loss of perceived core traditional cultural values. Arguably in this period the figure of the adolescent changed qualitatively in Japanese culture, rising to prominence within youth panic discourses circulated by the Japanese news media. These concerned the perceived rise in antisocial and problematic teenage behaviour, including the otaku, the hikikomori shut-in, classroom disobedience, bullying, and prostitution, while multiple cases of brutal murder perpetrated by teenagers became the focus of extensive media coverage. Public discourse expressed alarm at the perceived breakdown of the traditional family and the growing commodification of childhood in Japanese culture. This thesis develops understanding of the shifting attitude in Japan towards adolescence within the context of these cultural anxieties, and through the analysis of anime and videogames suggests strategies that are at work within popular cultural texts that are the product of, contribute to and reorient debates about the position of the suddenly and inescapably visible teenager in Japanese society. Through analysis of discourses relating to the shifting representation of the wandering adolescent as it moves across cultural texts and media forms, the thesis forms an original contribution to knowledge and understanding of Japanese anime and videogames through illumination of a prominent motif that to date remains unexamined.