This article explores Japanese literary engagement with the Caribbean island of Jamaica, one informed most directly by the recent popularity of Jamaican musical culture in Japan. I link these works to a discursive imagination of the international, including the Third World, as a proving ground for artistic accomplishment and for the acquisition of an ideological cosmopolitanism counterposed against life in insular Japan. This includes the discourse of jibun sagashi, or self-searching, that has emerged in the post-1991 recessionary era. I argue that a consistent trope in many works of fiction and non-fiction on Japanese travel to Jamaica is of their protagonists' or authors' intimate encounter with Afro-Jamaican blackness as both menacing and impoverished, but also vitalizing and endearing. Encountering the Afro-Jamaican, and surviving it, simultaneously affords a sense of toughness and sociopolitical enlightenment impossible elsewhere in Japan. I conclude that although these narratives usually include returns to a Japanese homeland appreciated anew, an ethnographic perspective on these issues - though not the focus of the paper - suggests that the experiences of less famous Japanese youth travelling to Jamaica might complicate these narratives offered to mainstream audiences. [ABSTRACT FROM AUTHOR].