Singapore is a highly urbanized city-state, so arguably all sports assume an urban nature and constitute an urban sports culture. Using skateboarding as a lens, this article examines how its history in Singapore reflects the Singaporean state’s governmentality and general attitudes towards youth in the country. More specifically, the article suggests that Singaporean statesmen and policymakers, in response to greater challenges from an increasingly educated and liberal-minded populace that demands alternative expressions of freedom and personal aspirations, have refashioned and even encouraged skateboarding as a productive sport that can channel youth energies away from delinquency and endear the state to young skateboarders, who are generally teenage boys. Skateboarding thus forms an integral part of Singapore’s urban sports culture, as evidenced by the creation of skateparks in both the downtown and heartlands and the popularity of skate videos on the internet. Skateboarding, once a symbol of an undesirable masculinity displayed by supposedly idle and boisterous young boys, now presents an alternative masculinity of active and energetic youth that coexists with the hegemonic masculinities of male technocrats and academically successful students.