This paper is a preliminary inquiry into the unique interplay between nationalism and cultural perception in Singapore, borrowing from Phillip’s (1950) notion of cultural cringe — the idea that local culture is deemed inferior to that of foreign entities. Despite being a hub for global cultural exchanges, Singapore’s local arts and cultural practices are often devalued by its locals. This is evident in local sentiments that suggest Singapore lacks a distinctive culture or produces inferior cultural products. This study focuses on Singaporean youth, who stand to be future producers and consumers of culture. By tracing Singapore’s national history, we aim to elucidate the intertwined relationship between this sense of cultural inferiority and the nation’s identity and nationalism. We argue that those who align more strongly with Singapore’s nationalistic attitudes are less inclined to develop attitudes of cultural cringe, viewing local cultural expressions not as subpar Western replicas but as emblems of Singapore’s national prowess.