Filmmakers have had to take into account certain restrictions whilst keeping their stories authentic, and tried to align themselves with the national agenda whilst playing into audience's tastes. The lack of local support pushed filmmakers to take on second jobs in order to continue creating their art, further reflecting the volatile situation that filmmakers are facing. Filmmakers also typically fall into two categories: commercial and arthouse. Commercial filmmakers like Jack Neo pander to local audiences, but his films have been criticised for their lack of any cinematic qualities. Arthouse filmmakers like Anthony Chen continue bagging awards around the world, but fail to make an impact locally. This research paper poses the overarching question: how do Singaporean filmmakers measure success in Singapore’s film industry? The paper also asks the following supporting questions: how do filmmakers appeal to local audiences whilst maintaining marketability overseas? Is the current film industry sustainable? What role do Singaporean films play within the country’s cultural narrative? This paper hopes to ultimately aid filmmakers by providing a clearer understanding of the industry, in order to help determine their position within the industry and our overarching national narrative.