In this article, I explore the representations of perpetrators of human rights violations in post-dictatorial Chilean cinema, specifically in documentary film. My objective is to examine how cultural memory has been produced through several cinematic productions. To this end, I focus on the representation of perpetrators in a corpus of four contemporary documentary films: El Mocito ('The young butler', Marcela Said and Jean de Ceartau 2011), Viva Chile Mierda ('Long Live Chile, Damn It!', Adrian Goycoolea, 2014), El Pacto de Adriana ('Adriana's pact' Lissette Orozco 2017) and El Colour del Camaleon ('The colour of the chameleon', Andres Lubbert, 2017). I argue that cultural memory has gradually expanded the imagination with respect to what is at stake in encounters with perpetrators in the post-dictatorship. The way in which this encounter is resolved in different documentary films is relevant to acknowledging the narratives and meanings of state violence in the post-dictatorship, as well as the tensions around the implementation of the transitional project and its fractures.