In this thesis, I demonstrate that the historical, and ideological, trajectories of HIV/AIDS discourses mirror the tensions between the local, global and transnational in my analysis of selected Anglophone Caribbean and South African literature and film. My methodology is adamantly a comparative studies approach as I overview the broader socio-historical narrative of HIV/AIDS whilst concurrently incorporating the idea of texts as always inflected by the wider historical and ideological processes behind transnationalism. I then link the competing histories of HIV/AIDS with textual depictions of HIV/AIDS, Indo-Caribbean histories, black Atlantic histories, and same-sex desire whilst foregrounding the socio-historical backdrop of transnationalism since the colonial period. A central thread running throughout is that transnational dialectics signify both the effects of the past on the present and the importance of comparative analyses for transnational textual engagements. Texts under discussion are the feature film Dancehall Queen by Rick Elgood and Don Letts, the novel The Swinging Bridge by Ramabai Espinet, the documentary film The Darker Side of Black by Isaac Julien, the feature film Children of God by Kareem Mortimer, the novella Welcome to Our Hillbrow by Phaswane Mpe, and the feature film The World Unseen by Shamim Sarif. Given the concurrent focus in postcolonial/queer around specific regional histories, I pinpoint that the dialectics between local, global and transnational discourses convey more nuanced, yet also more contradictory, textual engagement(s) with HIV/AIDS, transnationalism, sexuality, gender and ethnicity than some of the dominant narrative threads and debates surrounding postcolonial/queer. This point is particularly stressed in light of how many postcolonial/queer discussions readily fix the idea of the local as distinct from the global and the transnational. I thus re-read the contradictory registers of these discourses whilst foregrounding the relationship between these and HIV/AIDS discourses since the 1970s. I concurrently situate ny transnational comparative approach within the broader field of postcolonial/queer theory and approaches.