This exposition is a semi-dialogical inquiry into the potential of the methods and poetics of estrangement in documentary and political cinema, where we focus on the representation of the “neoliberal condition” in present-day society. We reflect on and rethink ideas that stem from various theories and strategies of emancipatory practices in cinema and literature. Here we acknowledge the tensions between conventions in for example social documentary, political cinema, and different conceptions of realism versus the idea of estrangement as an artistic strategy. The struggle to emancipate spectatorship and readership from the passivity and uncritical temptations promoted by the spectacles of the hegemonic culture industries has been a central concern in theoretical debates and artistic praxis that involves estrangement as a technique. How do Jacques Rancière’s notions on emancipation and radical equality challenge Brechtian ideas and methods of estrangement? How could the lineages of Third Cinema and testimonial literature help to rethink these matters today? What are actually the relevant means of estrangement in contemporary documentary art and literature?