Australia's northern-most tropical city of Darwin has a strong presence in the domestic and international touristic imagination as a tropical escape destination - a small city poised on the edge of outstanding natural beauty - yet in national cinematic representations Darwin is often presented as a frontier zone, whether these tropes are pivoted around culture or nature. I would like to take up this idea of the city of Darwin as special and distinctive in the national imaginary that is discernible in recent Australian cinema, an idea that I show extends to the city's representation in theatre and literature. This paper performs a close textual reading of the city's recent representation in two high profile Australian feature films, Charlie's Country (Rolf de Heer, 2013) and Last Cab to Darwin (Jeremy Sims, 2015). These are films that employ compassionate, humanistic themes, each maintaining a strong focus on main characters who find themselves both marginalized and neglected within the broader mechanisms of Australian society: hence each film is simultaneously performing the secondary work of critiquing Australian culture. In both films, I show how the tropical city of Darwin operates as a space of difference, but unlike the contemporary tourism marketing that simplistically brands the region as a "site of desire", here we find two unique critiques of Australian law and society that work to show the ethical frontiers of legislation and of human sovereignty.