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This study examines how Latinidad can be reclaimed as a site for exploring affinities of Latinos in Latin music industry, especially from the 90s. By looking at sites where Latinidad is constituted, such as the case of Jennifer López becoming Selena, it intends to suggest that the concept can be deployed as a political bridge to connect latinos. And by examining Cuban-American artists' self identification in Latin Grammy Awards, it reveals that the latin music business definitions of Latinidad is coded differently for them as 'Caribbean' to erase a natural resonance of Cuba. In addition, by dealing with Shakira's somewhat contradictory representation of Colombianidad, the study argues that Latinidad serves as a social construct and newly emerges as a convenient interstitial place between the Latin American and the US Latino. Shakira's case serves to show how the transnational trends of latin music contribute to create a simultaneous sense of Latinidad and Colombianidad. Focusing on the commercial significance of understanding of what latino is or should be, this paper aims to interrogate current understandings of Latinidad in the realm of latin music and popular culture.