Snowboarding and skateboarding are two of the most popular “action” or “extreme” sports. Born in the second half of the 20th century, these two board sports came of age in the global media spotlight. They rapidly grew in popularity, representing a youthful counter-culture to mainstream sport. Rejecting the rule-bound and competitive structures of traditional sport, snowboarding and skateboarding were athlete-led and resistant to organisation systems, such as international federations and the International Olympic Committee. Despite this rebellious stance, both sports conformed to traditional modes of exclusivity, with women and minorities often kept to the margins. This chapter explores the origins, history, development and global reach of snowboarding and skateboarding. We will highlight the contentious dynamic between athletes and governing bodies of sport, as we follow the development of snowboarding and skateboarding from fringe sport activities to popular Olympic features.