This dissertation challenges conciliatory views of Caribbean identity and epistemology by highlighting a series of texts and authors that question celebratory approaches to racial and sexual difference. I argue that negative relationality constitutes and epistemological and aesthetic alternative to reevaluate hegemonic representations of the Caribbean, one that dwells on antagonism, excesses, and exceptions that constitute the underside of an exceptional and affirmative view of the region. To do so, I understand negativity as a three-fold approach: a philosophical critique of stable identity and totality; a claim for the autonomous production of aesthetic discourses and its sovereign intervention in the public sphere; and an emphasis on the corporeal as the embodiment of psychic and social incoherence and disobedience. This approach allows me to focus on authors and artists from Colombia, Cuba, and the Dominican Republic that not only question identity as a discursive construct, but also through the ways in which the (re)mediation of these discourses into literary, audiovisual, and artistic forms opens up spaces to think about alternative modes of relation with racial and sexual difference.