The current article links masculine leisure with bodily performances and playfulness connected to global neoliberal expressions of gender, class and ethnicity. This study draws from an analysis of a skateboard video of young white middle-class men skateboarding in an urban environment in one of Sweden’s greater metropolitan areas. An interview with the young man who created the video was also conducted. The analysis brings together lines of inquiry that concern young males’ playful use of urban space with the articulation of the visual culture of skateboarding as a homosocial, mainly white middle-class practice where bravery and risk-taking are essential articulations. We argue that the skateboarders articulate masculine subjectivity by a complex amalgam of playfulness, risk-taking, colonization of space and the visual style involved in their skateboarding. The construction and presentation of self in the skateboard video are integrated with the quest for individual identity, self-realization and meaning making that pertain to a global entrepreneurial mindset in which mainly white middle-class men are privileged.