Risk societies (Beck, Risk society: Towards a new modernity. Sage, 1992) regularly present situations that exceed individual capacities for control, certainty, expertise, and knowledge—ranging from toxic exposures to climate change to legalised gambling to high-dose pharmaceuticals. Risk markets—licit and illicit, regulated and unregulated—deliver intense and potentially lethal experiences. Building from the experiences of extreme athletes, this chapter offers a new frame for ‘risk regulatory societies’ that order time and space in ways that fuel oscillation between risk and safety as a basis for identity. They heighten emphasis on safety, compliance, and insurance to anchor social norms and routines of risk avoidance in everyday life while also promoting “cultivated risk-taking … in which danger and its resolution are bound up in the same activity” (Giddens, Modernity and self-identity: Self and society in the late modern age. Stanford University Press, 1991, p. 133). Today ‘cultivated risk-taking’ is curated in lifestyle risk markets promoted through mass and social media. Yet participation in it is often framed as ‘addictive’ and individuals seeking out risky or extreme situations are studied as ‘sensation-seeking’ or ‘thrill-seeking’ ‘edgeworkers’. This chapter reviews the scholarly literature on extreme sports, an umbrella term for a genre of diverse activities that demand participants engage with risk in unique, skill-based ways, and examines the construction of addiction to extremity as a social scientific research object.