São Tomé, a small island in the Gulf of Guinea and a former Portuguese colony, is an exemplary place to analyze the development of plantation “cropscapes.” These cropscapes emerged around sugar in the sixteenth century, evolved with coffee in the 1850s and consolidated with cocoa from the 1880s onwards. While is impossible to ignore the monocultural nature of São Tomé plantations and the centrality of specific plants for these plantation ecologies, there were other human/plant assemblages, that sustained, subverted or ran parallel to plantation goals of production, profit and power. This article zooms into cannabis to explore different relations between plantation working peoples and plantation environments, between suffering, healing, and violence, between labor, pleasure, and power. It will examine how cannabis was part and parcel of the lives of peoples from Angola recruited to São Tomé and, consequently, of the island's plantation worlds in the late nineteenth century. It will also discuss how colonial discourses on cannabis obscured and silenced the presence of this plant in contemporary plantation histories, regardless of its traces in the archive. Cannabis histories are in fact important ones: they counter imperial master narratives by showing how, even under conditions of exploitation, laboring communities and plants co-produced spaces of autonomy, care and leisure.