Exploring the shifting ground of the relationship between street art and transgression, this article analyses the dislocation of street art from its traditional geographies of deviance and, in the era of advanced commodity culture, investigates the possibilities for understanding this art form as a socially engaged spatial practice. Embedding contemporary street art in the artistic practices of Surrealism and Situationism, the article traces a lineage of graffiti's associations with protest and the street through to its current manifestations within some of the world's most established 'white cube' gallery spaces. In attempting to avoid the inevitable melancholic readings of street art as commodified sign, the paper argues for the importance of considering the locatedness of the work in any evaluation, and thus moves to read street art in correspondence with the urban spaces in which it performs.