The construction of Singaporean identity can be traced through the Singapore filmmaking industry with two most prominent filmmakers in Singapore, P. Ramlee and Jack Neo portray Singaporean identity through several approaches. Though P Ramlee is Malaysian, he plays such a crucial role in the construction of Singaporean identity as studios like Shaw Brothers where he worked, was based in Singapore. He presents Singapore through the economic lens, called “Cultural Materialism” in which money was given the prominence in P Ramlee’s movies. His movies are an implicit portrayal of Singaporean where he implies the idea that Singaporeans are inherently tied to or constantly navigating the importance of wealth and economic success. In continuation, Jack Neo adds his own nuance in the portrayal of Singaporean identity in his movie, focusing on Chinese-Singaporean. He portrays them based on their vernacular practices (traditional values and practices) and the use of various dialects while also adding critical discourse towards the government. However, Neo’s movies are widely contested as to whether his work is to perpetuate the hegemonic of the state or to counter them which leave a modern contestation of tradition and modernity where traditional practices are seen to be deprioritized over government modern projects (the use of English is prioritized), making Chinese-Singaporean people risk their cultural identity. The method used in this paper is qualitative where the writer analyzes based on movies produced by P. Ramlee (Bujang Lapok in 1957) and Jack Neo (I Not Stupid in 2002) and supported by several journal articles.