An important and mounting issue for the contemporary Olympic Movement is how to remain relevant to younger generations. Cognizant of the diminishing numbers of youth viewers, and the growing success of the X Games – the ‘Olympics’ of action sport – the International Olympic Committee (IOC) set about adding a selection of youth-oriented action sports into the Olympic programme. In this article we offer the first in-depth discussion of the cultural politics of action sports Olympic incorporation via case studies of windsurfing, snowboarding, and bicycle motocross (BMX). Adopting a post-subcultural theoretical approach, our analysis reveals that the incorporation process, and forms of (sub)cultural contestation, is in each case unique, based on a complex and shifting set of intra- and inter-politics between key agents, namely the IOC and associated sporting bodies, media conglomerates, and the action sport cultures and industries. In so doing, our article illustrates some of the complex power struggles involved in modernizing the Olympic Games in the 21st century.