This paper explores the role of digital media and creativity in the processes of learning that occur in groups of urban skateboarders. In particular, it examines how the production and consumption of amateur videos contribute to both skaters' mastery of the techniques of the sport and their integration into the culture of the sport. The data come from an ethnographic study of skateboarders in Hong Kong, which included in-depth interviews, participant observation and the collection of texts and artifacts like magazines, blog entries and amateur skating videos. Skateboarders use video in a number of ways that significantly impact their learning and integration into their communities. They use it to analyze tricks and techniques, to document the stages of their learning and socialization into the group, to set community standards, to build a sense of belonging with their "crews" and to imagine "idealized futures" for themselves and their communities. Understanding the value and function of such "semiotic mediation" in learning and socialization into sport cultures, I suggest, can contribute to helping physical educators design tasks that integrate training in physical skills with opportunities for students to make meaning around their experiences of sport and physical education. (Contains 1 note.)