This study attempts to consider the significance of the Singaporean heartland film by examining how issues of social conformity, hierarchy, and ordering are configured into a dystopian imagination of the heartlands. The researcher argues that the significance of the genre lies in its attempt to destabilize official narratives regarding society, culture, and community by depicting stories of deviance and dysfunction in the heartlands. The methods used in this article involves discourse and textual analysis to identify the recurring patterns, themes, and motifs of the genre. Three major themes emerge from the analysis; (1) the visualization of the dystopian city, (2) the breakdown of the family unit, (3) and general pessimism towards contemporary life in Singapore. However, the analysis also reveals gaps that currently exist in its current configuration. These include tendencies to romanticize a nostalgic past, to eschew social and cultural diversity, and to reinforce narratives of repression and angst in the nation.