Over the course of this paper, the overall role and effect street art has on a city and its development will be discussed. It will touch generally on the topic of street art history and how it stems from graffiti practices. While also mentioning two well known street artists that changed how the form can be perceived and applied to the streets, ultimately being a factor in growing city environments. The difference in definitions of street art and graffiti will also be discussed with reference to its overall subjectiveness, followed by street arts interconnectedness with the law. This will lead up to street art and whether it is a factor in gentrification and how this plays a part in the creative city. It will discuss later if keeping street art out is the response to stop gentrification, while also adding to the idea that street art is selling a false sense of city beautification and used as a ploy marketing tool. Several options of art-led gentrification will be analyzed, as well as its varying effects on the planning of a city. Eventually, this will all lead to an analysis of Roosevelt Row and how the presence of street art within the arts district will cause the district to grow and develop in the future, as it becomes a prime location in the contexts of the revitalizing downtown area.