This dissertation examines representations of gay men in contemporary Japanese novels and films produced from around the beginning of the 1990s so-called gay boom era to the present day. Although these were produced in Japanese and for the Japanese market, and reflect contemporary Japan’s social, cultural and political milieu, I argue that they not only articulate the concerns and desires of gay men and (other queer people) in Japan, but also that they reflect a transnational global gay culture and identity. The study focuses on the work of current Japanese writers and directors while taking into account a broad, historical view of male-male eroticism in Japan from the Edo era to the present. It addresses such issues as whether there can be said to be a Japanese gay identity; the circulation of gay culture across international borders in the modern period; and issues of representation of gay men in mainstream popular culture products. As has been pointed out by various scholars, many mainstream Japanese representations of LGBT people are troubling, whether because they represent “tourism”—they are made for straight audiences whose pleasure comes from being titillated by watching the exotic Others portrayed in them—or because they are made by and for a female audience and have little connection with the lives and experiences of real gay men, or because they circulate outside Japan and are taken as realistic representations by non-Japanese audiences. In this dissertation I argue that positive, supportive, indeed overtly political messages can be found, even in texts with problematical representations. I show that, over the nearly twenty year period covered by the novels and films I study, it is possible to discern a tendency towards less stereotyped, and more overtly political, portrayals. The novels and films I discuss in this dissertation represent a disparate range of genres, producers, and representations, and characters who are straight, gay, bisexual, transgender and transsexual. Yet all have in common the universal themes of overcoming or becoming, ranging from journeys to coming out, growing up, and finding the self to stories of triumphing over homophobia and prevailing over discrimination.