Over the course of the last several years an increasing number of artists, critics and scholars have begun to (re)examine the relationship between artistic and geographic practices. This has brought about a proliferation of hybridized artistic projects, exhibitions and texts. While a number of the works raise important issues and engender dialogue, the saturation of the art market has also resulted in the production less cohesive and thought-out projects This project focuses on a very specific subset of the intermingling between artistic and geographic practices: artistic experimentations with cartography. In an effort to examine the political efficacy of such experimentations, I concentrate on three distinct but similar artistic projects. The first chapter discusses Guy Ernest Debord's 1957 map of Paris titled The Naked City, arguing that the political efficacy of the work lies less in its Marxist critique of official cartographies, and more in its affirmative capacities. The Naked City functions not only as an expose of the homogenizing processes of capitalist spatial representation, but also as a map of the Situationist derive. It thus breaks down the original form - in this case the Plan de Paris - while also creating the space for potential new forms to arise. With this expanded understanding of The Naked City in place, the second chapter discusses Jane and Louise Wilson's 2003 video installation, A Free and Anonymous Monument. Like Debord, the Wilsons utilize appropriation and fragmentation as a means of critiquing the homogenizing processes of capitalist representation, specifically those in Northeast England. While acknowledging the particular affinities between the The Naked City and A Free and Anonymous Monument, I also argue for a more expansive understanding of the Wilsons' work. Following Deleuze's own project to re-think the nature of the simulacrum, I argue that A Free and Anonymous Monument exhibits the positive potentialities of the simulacrum, thus shifting representational repetition even further away from critique and toward affirmation - from Debord's detournement to Deleuze's simulacrum. The third chapter follows a very similar route, reprising and then abandoning Debord's Naked City. It focuses on Notes for a People's Atlas of Chicago, an ongoing collaborative project begun in 2005 by Daniel Tucker and the interdisciplinary non-profit AREA Chicago. While recognizing the critical role that the work of the Situationists and more specifically, The Naked City play in NPAC, I also link the project to Earth art and the history of site-specificity that arises from it. In her seminal text, One Place After Another, art historian Miwon Kwon asserts that the numerous variations of a community that arise from community-specific artistic collaborations, reveal its ambiguous and problematic nature. Taking Kwon's arguments into account, I contend that The People's Atlas both recognizes and propagates the unstable and fragmentary nature of both site and community. Thus, NPAC functions as a minor art. It not only serves as a literal topology of radical subjectivities, but also involves a diagramming of becoming, summoning its audience into being. In transferring the production of the map to community members and non-experts, the project aims to create a more democratic and collaborative production of space and knowledge.