The association of Caribbean literature with notions like identity and resistance has had a long intellectual trajectory. 1 A central theme in the literary and artistic representation of Caribbean resistance has been a meditation about the legacies of colonialism and the alternative master narratives that have been provided by postcolonial and decolonial frameworks. I therefore propose, as a theoretical experiment, a review of the some iconic works of Caribbean literature written between 1930 and the 2000s by establishing a dialogue with three distinct intellectual traditions in which the notion of colonialism and cultural representation have been key: Latin American colonial studies, postcolonial theory, and the decolonial turn. This experiment presents some advantages, as well as some limitations and challenges. On the one hand, it allows us to think about the long durée of resistance and colonialism as a central topic informing aesthetic and poetic projects in the Caribbean. On the other hand, since the essay proposes a survey of some of the authors and texts from the Caribbean region, my exposition could create an illusion of chronological progression or teleology of theoretical approaches and particular topics. This is not my contention here, but I take this risk as a hopefully productive exercise to reimagine artistic and political resistance in the Caribbean.