The popularity of slain American hip-hop star Tupac Shakur has become a global barometer of youth malaise. Taking a multidisciplinary approach that weaves social history, cultural studies and globalization studies, this paper highlights the convergence of socioeconomic alienation and media proliferation since the early 1990s. It argues that this confluence has given rise to new global heroes such as Tupac, icons that have become components of a planetary symbolic lingua franca that has yet to gain significant analytical attention. The paper outlines the transnational import of Tupac by considering combatants’ evocations of him during the Sierra Leone civil war (1991-2002). Militant factions’ attraction to Tupac – their use of Tupac T-shirts as fatigues and incorporation of his discourse into their world views – offers insight on how young people have sought broader relevance for their particular experiences through the imagery of global popular culture. Tupac references allow for a powerful stereoscopy; they reveal mediated communities of sentiment as well as the psychological traumas of violence and social alienation. The symbolic discourse of Tupac imagery during the Sierra Leone war thus expands the relevance of a civil war to broader patterns of alienation while revealing planetary sentiments in the minutia of Sierra Leone’s devastation. Bibliogr., notes, ref., sum. [Journal abstract]