Understanding and defining nation and identity in diaspora has long characterized the cultural production of Caribbean authors. Notwithstanding, Hispanic Caribbean authors that have emigrated to the United States face this question doubly as they form part of what is labeled the Latino community. While much of the Latino Studies groundwork began in Mexican American or Chicano literary circles, whose cultural background is vastly different from that of the Hispanic Caribbean, authors of Cuban, Dominican, and Puerto Rican descent have brought new perspectives to constructions of race, class, gender, and sexual orientation to the broadly named “Latino/a” experience. While much of the early theoretical and literary work was written by men, women writers began to produce prolifically in the late twentieth century. The first voices to be published in mass were primarily those of a privileged existence, coming from families of higher social classes within the Latino community, despite being marginalized within the context of the United States. During the late 1970s to early 1990s, literary production established that being Cuban American, Dominican American, and Puerto Rican in the mainland U.S. meant being light-skinned, heterosexual, and of middle to upper-class economic status. However, during the mid-to-late 1990s and early twenty-first century, new voices came to the forefront to challenge these hegemonic constructions of Caribbean Latina identity that dominated the cultural imaginary and, instead, presented intersectional protagonists who consistently face discrimination based on their gender, sexual orientation, race, and economic class both in and outside of the Latino community. By utilizing diverse strategies of resistance, such as humor, these authors, including Achy Obejas, Jennine Capó-Crucet, Loida Maritza Pérez, Angie Cruz, Giannina Braschi, and Erika López, highlight and satirize the normative aspects of the Hispanic Caribbean diasporic cultural imaginary that marginalizes and/or excludes the voices and experiences of their characters as being representative of Caribbean Latina identity. In this sense, these authors not only represent a marginalized perspective of identity within the Latino community, but they also re-present, as in presenting anew, a more diverse image of Latina identity in the twenty-first century that departs from the homogenous, normative image of Caribbean Latinas played out in earlier narratives of identity from the early-1990s Latina literary boom.