This current study focuses on the effects of neoliberalism on the Chilean sociopolitical period of postdictatorship (1990–2010) by studying a new generation of filmmakers in the work of Alberto Fuguet. In the trilogy of Se arrienda (2005), Velódromo (2010), and Música campesina (2011), Fuguet reviews the flâneur figure exploring the aesthetic of detachment and disaffection in the contemporary urban space, a topic that has become critical in Chile’s postdictatorship. As they cross urban spaces, these characters oscillate between estrangement and detachment from a local identity, a past time and/or origin. They are flâneurs embodying a division between time and space, incarnating a melancholic view towards the past, present, and future. Distant from their community, these individuals are unable to participate in any collective project. This feature of Fuget’s filmmaking arguably reflects a Chilean sociopolitical trend of the postdictatorship period, whereby filmmaking has adopted a repression of memory and history that mimics the tension between resistance and adhesion to the neoliberal model. I propose that this sort of political detachment is the result of what I call the politics of detachment of the Chilean postdictatorship as depicted in Fuguet’s understudied cinematography.