The primary goal of this paper is to examine the ways in which legal and sanctioned “street art” features as a prominent tool in the recent attempts to revitalize and rejuvenate one of the most storied and historically important cities in the world: Detroit, Michigan. It will do so first by examining some of the factors that hastened Detroit’s decline from urban, industrial powerhouse to universally recognized symbol of post-industrial urban decay, and back again, to its present, albeit tenuous, status as celebrated emblem of urban regeneration. This is done so as to explain why the efforts to “save” Detroit in general are concentrated on such a small tract of land in the city’s downtown core or “Central Business District” (CBD). Second, it will examine key planning documents jointly authored by stakeholders in the public and private sectors, that regard commissioned street art projects (such as Shepard Fairey’s mural on the Quicken Loans Headquarters) as strategic aesthetic levers that attempt to author new narratives in the collective imaginary regarding the present and future of the troubled Motor City. Third, it draws on extensive field research undertaken in Detroit’s CBD so as to argue that street art projects are important, but are also limited in their capacity to engage broader audiences/publics due to their being locked in situ. Fourth and finally, the role of technologies not traditionally associated with graffiti or street art (mobile digital cameras and social media) are regarded as pivotal to its reframing and current embrace by property developers and municipal officials. By leveraging the communicative capacities of ubiquitously connected mobile devices and their ability to capture and disseminate digital photographs of street art, the reach of these photographs extends far beyond the limited physical confines of city streets, accessing publics accustomed to seeing vastly different photographs of Detroit. It is these digital and eminently social photographs, so often neglected in the academic literature, that are the visio-narrative devices being used to author the next chapter of Detroit’s fabled history.