The landscape of Latin American celebrity representation, typically understood through the theoretical lens of cross-over, is undergoing significant shifts. The Colombian rockero Juanes's career, press reception, and participation in the transnational public sphere have established him as a celebrity diplomat. Read against the star texts of previous cross-overs, Juanes's economic success and the international attention his political efforts have garnered suggest a dynamic shift in the agency and representational strategies available to Latin American celebrities. His ability to succeed in this realm is contingent on a performance of hegemonic heterosexual masculinity. A critical discourse analysis and transnational feminist approach traces the production, circulation, and discourse of the music, press reception, and production of Juanes's celebrity and philantrophic/political efforts.