This thesis is the first extended study to consider the representation of (old) age and ageing in postcolonial literatures and film productions from Aotearoa New Zealand and the Caribbean. It explores the fault lines and intersections between, on the one hand, postcolonial studies, and age studies, critical gerontology, and dementia studies on the other. I argue that strategies aimed at the ‘diversification’ of these latter disciplines often ossify, romanticise, or even instrumentalise ageing Indigenous and Caribbean figures. In contrast, I advance a postcolonial ageing studies methodology to explore the stakes and possibilities of age and ageing in Aotearoa New Zealand and Caribbean texts. In reclaiming these works as representations of age, my readings demonstrate that ageing inaugurates distinct responsibilities and embodied and cognitive points of difference that enable older people to address issues such as land dispossession; threats to intergenerational health and wellbeing; exploitative care relations; and colonial trauma. Age and ageing are thus figured in these texts as interrelated loci for reimagining intergenerational relations beyond the colonial legacies pervading Māori and Caribbean communities. In making these connections, I foreground age as a hitherto unexplored platform for the comparative study of Aotearoa New Zealand and the Caribbean. My analysis of these heterogenous representations allows me to cultivate new theorisations of age such as spiral kaumātuatanga (elderhood), trickster performativity, and dementia-gain. This thesis contributes to the methodological reorientation of age-related studies and postcolonial critique as I pursue situated ethical models of interdependency, agency, and care beyond the individualist, ableist, and productivist norms of neoliberal societies. Ultimately, this thesis takes the first steps to establish postcolonial ageing studies as a necessary frame for our understanding of ageing in a world marked by colonial modernity and its continued global manifestations