This paper investigates the methodological use of Ottoman-era literary works in Arabic, with comparative discussion of Ottoman Turkish and Classical Malay literary works, as historiographical sources for an analysis of transimperial notions of selfhood and difference. The 15th and 16th centuries saw the rise of global networks of trade in spices and silk commodities connecting Central America and the Mediterranean to Central Asia and the Indian Ocean. The archival evidence in centers such as Venice, and Istanbul, and the Netherlands reveals a complex political history of imperial administrators formulating key legal strategies that fostered the global economic activity of multiconfessional networks of merchants and diplomats. While certain archival documents are conducive of a specifically cultural analysis of these transimperial encounters and exchanges, these documents can be contextualized further through a careful examination of often-overlooked literary sources that offer narrative representations of early modern trade routes. Drawing on selections of key literary works, including the Arabic navigator Ahmad ibn Mājid’s (d. 1500) surviving corpus of Arabic poetry and prose, the merchant ‘Ali Akbar’s Ottoman Turkish Ḵeṭāy-nāma on China, and the Classical Malay Sejarah Melayu, this paper asks whether the globalizing trends of transimperial commerce and subjecthood in the 15th and 16th centuries allow historians to speak of changing notions of self and difference along the trade routes connecting the Mediterranean with Central Asia and the Indian Ocean.