This dissertation pursues the argument that New York Style Writers (often misnamed as “graffiti” based artists) transformed a transportation infrastructure system into a communication technology. The introduction focuses on a series of popular culture anchors from Basquiat to the films Wildstyle and Style Wars, guiding the reader through the basic shapes and concerns of the practice as it developed in the later 20th century. Then, in chapter 1 I begin by historicizing their practice within the longer history of metropolitan development in New York City, specifically the automobile focused development priorities which occurred at the cost of the subway’s growth. Alongside those funding priorities, I examine the broader systems of racism and social defunding which occurred throughout the city, especially in hip hop’s birthplace. In Chapter 2, I inquire about the aesthetics of sociability behind the development of the subway as a communication network, relying on the modernist approaches of Carlos “Mare 139” Rodriguez. In Chapters 3 and 4, I inquire further about the aesthetic methods which allowed the subway to be transformed into a communication system, specifically considering compression and identity strategies on behalf of Rammellzee’s preoccupation with mathematics and technology. Chapter 5 takes a deeper look at the municipal mechanisms and informatics which led to widespread devolution, especially in racially marginalized areas of the city, and traces these problems into the longer term future of the city (into the 21st century). Chapter 6 continues the investigation into themes of technology among Style-Writers, specifically considering the work of Kase II and the ways that his “computer style” negotiated stylistic concerns arising in the digital age. Keeping in mind Mare’s commentary that the subway resembles the architecture of the internet, I turn to the work of Skeme and his favored production area, the 3 train yard in Harlem, considering his claims for intuitive algorithms. The conclusion extends the questions of technology and computation by asking what theories of artificial intelligence may learn from the insights of the Style Writers.