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My paper argues that the contemporary theories of postcolonial criticism have inadequacies in accommodating the plurality of experiences in the pre/post – colonial literature. And hence the paper proposes ‘double occupation’ as a better mode of approach towards postcolonial criticism. First, this paper explores the image of Africa in TD Ramakrishnan’s novel Mama Africa (2019) and Meena Alexander’s poems “Manhatten Music” (1997), “Art of Pariahs” (1996), and “Port Sudan” (2002). The narrative in Mama Africa unfurls through the perspective of the protagonist Tara Vishwanath who is an African author of Indian origin. TD Ramakrishnan writes in Malayalam whereas Meena Alexander's poems are in English; which are shaped by her diasporic experiences in Sudan as a Keralite or as an Indian. Located in the horizon of ‘Afro – Indian’ experiences, her three poems reflect on the issues of exile, affinity to roots, migration, and hybrid identities. As an example, the paper attempts to locate these works in the theoretical framework of Homi K Bhabha’s ‘hybridity’ and shows how the literary experience of cultural hybridity goes beyond Bhabha’s theorisations. In literature, the colonizer – colonized relation is constituted in diverse modes of interactions. Hence this paper calls forth a critical approach that can accommodate the plurality of experience as well as the analytical dimension of criticality. Inspired by Oren Lieberman’s idea of ‘double occupation’ and Lyotard’s theorisation of ‘figure/ground’, my paper argues that postcolonial criticism should simultaneously 'occupy' the plurality of ‘post conditions’ and the ‘normative definitions’ of criticality. While assuming a shared postcoloniality, the contemporary critical theory focuses on the ‘figure’ which denotes, in this case, the normative features of the postcolonial writings. And the heterogeneity of the postcolonial experiences gets blurred in the ‘ground’.