In this essay I argue that City Song enacts a performance of Vancouver that reveals as much about a city in the process of conscious redefinition as it does about the politics of representation in documentary film soundtracks, exposing key ideological overlaps between the making of cities and their cinematic representations. The film stages the city through a set of eight sequences, each roughly delimited by the performance of a particular song, and each offering its own distinct vantage point on the city with attendant shifts in rhetorical tone and aesthetic treatment. The songs cover a range of styles common within the folk repertoire of the day, and beat-style narration offers points of transition between locations. The Inquisition Coffee House is the hub of the film wherein several songs presented in synchronized performance reveal the source of the music we hear throughout the rest of the scenes. The issues facing the city are thus articulated and interrogated by way of musical performance, making City Song a striking (and strikingly early) exploration of what Stella Bruzzi refers to as the “performative” mode in documentary filmmaking (186). As I will demonstrate, City Song’s “performativity” is both troubled and enhanced by the way it intersects with issues specific to the music documentary (of which it is a also a relatively early example). I argue that this intersection is best understood as a process of the city’s self-representation that I will refer to as “staging” following recent work by Karin Bijsterveld (2013). This staging is only accessible by way of attention to the soundtrack, both in terms of the obvious thematic content of the lyrics and the loaded location in which they are sung and from which they carry over the rest of the film. Ultimately, the overt staging in City Song explores the potential for a film to engage actively in the re-imagining of a city, making it a model case study for how works of art can be used for serious soundscape research into urban actualities of the past.