Vigorous, expressionistic, and creative, skateboarding has become an increasingly popular activity worldwide. As more and more people begin to skateboard, their presence in urban centers has become more notable, and according to city officials, police, and business owners, more intrusive. A clue to why authority perceives skateboarding as a disruption to society lies within the physical designs and constructs of modern metropolis—symbolism through architecture. Architects and urban planners embrace the dominant cultural and political hegemony of capitalist society in their designs. Skateboarders perceive these objects differently, intentionally using these spaces in an alternative, contradictory way, undermining the social, political, and economic foundation of society. Central to this idea, skateboarders literally re-imagine and re-invent urbanity, transgressing society's idea of the 'appropriate' use of public space, or as social theorist Henri Lefebvre terms, the “production of space,” an economic idea which states that architecture's main goal is to affirm the economic functioning of capitalism by creating an environment which foster production-exchange-consumption activities, an idea cemented at capitalism's core. The transgression of such invisible social/political values has entirely visible consequences in the form of social and political repression. In order to understand how skateboarders engage in their activity in the public realm, the analysis begins with a brief foray into the history and subsequent progression of skateboarding from the “sidewalk surfing” of the '50s and '60s up through modern day street skating, in which the main focus of this paper lies. In order to fully grasp how and why skateboarding conflicts with dominant cultural norms, the skateboarder him/herself need to be understood. Therefore, subculture, its effects on identity, values, and its place within the context of larger culture is also explored.