As a respected cultural figure in Singapore who was posthumously honoured at the Pioneer Generation Tribute organised by the Ministry of Culture, Community and Youth in 2015, the story of Chua Boon Hean is one that goes beyond his role as an established poet in the field of Chinese literature in post-independence Singapore. This dissertation is an effort to elaborate on the story of Chua in Singapore and will attempt to examine his multiple roles and contributions in the socio-historical context of the film industry prior to 1965. Notably, he had played the role of an extraordinary assistant to the Shaw Brothers (Runme and Run Run Shaw) who would qualify as the two most important tycoons to exert profound changes in the development of the Chinese and Malay film industries by the mid-20th century. His life and career with the Shaw Brothers for over three decades since the late 1920s, prove to be critical to our understanding of the overall development of the film industry in Singapore, especially in the period before the colonial city became an independent nation on its own. This dissertation seeks to build on existing scholarships with a greater attention being placed on introducing the different participants involved in the film industry in Singapore before 1945 and how the industry gradually developed into an inter-locking "business of culture" during the early 20th century. It reveals that the development of the film industry in Singapore should be best studied together with its intersection with the field of literature, translation, advertisement (art studios) and amusement parks, as well as its instrumental role in shaping the mundane day-to-day experience for the local population. Contrary to the traditional framework of analysis of the Singapore film industry which tended to focus solely on film production and its content such as genres or storylines, emphasis will be placed on other aspects of the film industry especially exhibition and distribution, in order to present a more comprehensive background to its genesis. It hopes to illuminate how the multi-cultural character of the film industry was a product of the historical agency of individuals living through the period. This case study of Chua also illuminates the dynamism and diverse connections among different Chinese dialect groups in Singapore and the Straits-born Chinese during the early 20th century. Contrary to the perception that the overseas Chinese had been a homogenous group, it is critical to account for the heterogeneity which can offer a more nuanced picture of the Chinese society. Through the unique story of Chua, this dissertation seeks to enrich existing scholarships on Chinese migration and the film industry in Singapore. In the process, we also chart the multi-faceted and multi-ethnic interactions of the Chinese diaspora in Southeast Asia in the early 20th century