Hikayat Hang Tuah is a classical Malay literary text, contextualized within the 15th century political-culture of the Melaka Sultanate that is imbued with socio-political messages. Its discourse is, nonetheless, relevant to colonialist readers with Orientalist perspective reflective of the British colonizers in the Malay Peninsula (1874-1957) and also to contemporary indigenous readers. This article examines the ‘politics’ of reading Hikayat Hang Tuah, by comparing two reading perspectives, namely Richard O. Winstedt’s, which is from the Orientalist perspective, and that of the writer, which is from an indigenous and post-colonial one. It is the contention of this article that readings of HikayatHang Tuah are constructed by mindsets and intellectual paradigms of specific cultural and political leanings. The colonial politics and culture in Malaya of the late 19th to mid 20th centuries, not only shaped the Orientalist mind of the colonial officers and researchers, but they also operated to influence their readings of native texts by looking at the texts through the perspectives of leading theories of the period, namely evolution and diffusion. After colonialism, these same texts can be read from other perspectives within theories contemporary to this period, including post-colonial theory, which then generate new meanings.