This thesis is a comparative study of two documentary films made in and about the Montreal neighbourhood of Saint-Henri. Hubert Aquin’s À Saint Henri le cinq septembre (1962), and Shannon Walsh’s homage, Saint-Henri The 26th of August (2011) are at the centre of my investigation, which is concerned with the multifaceted ways these films represent, and sometimes, create uncanny effects in Saint-Henri. Its mediated uncanniness is discussed in psychological, technological and architectural terms. I explore the various methods used by the directors in their respective modern and postmodern approaches to represent the physical spaces of Saint-Henri, as well as the people who inhabited this post-industrial (1962), and now quickly gentrifying (2002) neighbourhood. Produced almost fifty years apart, these films exemplify transformations in both documentary film and community studies during this period. An examination of the connections between film, geography, economy, and the social and architectural make-up of neighbourhood, this thesis is a study of a community that, I argue, has been consistently under threat.