In this paper we examine how practices and logics associated with the cultural ‘outsider’ underpin one particular fusion of contemporary art, alternative sports, and marketing interests which are endemic to post-Fordist economies. We describe a skateboarding-infused art exhibit, Beautiful Losers, to investigate how power dynamics operate relative to post-industrial creative classes. In particular, we illustrate how Beautiful Losers is one example of an emerging social field that privileges ‘outsider’ dispositions and discourses. Bourdieu’s concept of symbolic capital is used to describe the interested parties and the struggles for legitimacy existing within the social field. We contextualize the social significance of ‘outsider’ discourses in consumer culture and how that has gained currency within post-industrial society. We then link the idealization of the cultural ‘outsider’ with contemporary discourses associated with alternative sport and artistic disinterest. Beautiful Losers distinctly merges these logics in ways that legitimate an ascendant version of ‘outsider’ masculinity. We provide insights into how the legitimation and reproduction of this ‘outsider’ masculinity represents a symbolic struggle for capital amongst participants and audiences. Arguably, symbolic capital was primarily afforded to the white male artists and founding members who came from middle-class backgrounds.