Art (paintings, installations, performance art) and film on the Caribbean offer vantage points for analyzing alternative ways through which the region has been thought, imagined and produced. They are periodized semiotic productions that feed into and are marked by perspectives that are at once global, national, and even personal. Considering the constitutive contexts of these productions and performances, we will attempt to glean the diverse perspectives, and the way these have influenced sociocultural policy and offer alternative interpretations of diasporic lifeways of Caribbean people.