This paper reveals and analyzes the cinematographic, political, and aesthetic transitions intersecting two Southern Cone films that premiered concurrently in 1991: the award-winning Chilean movie "La frontera" by Ricardo Larraín and the forgotten Argentine independent production "La redada" directed by Rolando Pardo. Despite bridging similar historical circumstances and tackling sensitive issues that rose to the forefront during the transition to democracy, "La frontera's" and "La redada's" editing techniques, treatment of characters, mise-en-scènes, and conclusions reveal divergent aesthetics that affected the films' reception at the time of their release and that deserve a close critical analysis. Not only can these artistic differences be interpreted in relation to the political moment of transition of the late 1980s and early 1990s in Argentina and Chile, but they also resonate with current discussions about inequality and discrimination in postauthoritarian society and the actual state of democracy in the Southern Cone.