This paper analyzes the scholarly approaches to the problem of “local” vs. “cosmopolitan” in the context of the cultural transfers between South and Southeast Asia. Taking the “localization” paradigm advanced by Oliver Wolters as its pivot, it reviews the “externalist” and “autonomous” positions, and questions the hermeneutical validity of the fuzzy and self-explanatory category of “local.” Having discussed the geo-environmental metaphors of “Monsoon Asia” and “Maritime Asia” as alternative paradigms to make justice to the complex dynamics of transregional interaction that shaped South and Southeast Asian societies, it briefly presents two case studies highlighting the tensions between the “local” and “cosmopolitan” approaches to the study of Old Javanese literature and Balinese Hinduism.