This chapter presents a comprehensive review of the interaction between circum-Caribbean indigenous peoples and nonhuman primates before and at early European contact. It fills significant gaps in contemporary scholarly literature by providing an updated archaeological history of the social and symbolic roles of monkeys in this region. We begin by describing the zooarchaeological record of primates in the insular and coastal circum-Caribbean Ceramic period archaeological sites. Drawing from the latest archaeological investigations that use novel methods and techniques, we also review other biological evidence of the presence of monkeys. In addition, we compile a list of indigenously crafted portable material imagery and review rock art that allegedly depicts primates in the Caribbean. Our investigation is supplemented by the inclusion of written documentary sources, specifically, ethnoprimatological information derived from early ethnohistorical sources on the multifarious interactions between humans and monkeys in early colonial societies. Finally, we illustrate certain patterns that may have characterized interactions between humans and monkeys in past societies of the circum-Caribbean region (300–1500 CE), opening avenues for future investigations of this topic.