Extreme endurance sporting events and participation in these events have grown exponentially since the 1970s. Events such as Iron-distance triathlons, marathons, ultramarathons, ultra distance cycling, and military-style obstacle courses now attract millions of participants in the United States annually. Although many studies have analyzed this late 20th and early 21st century phenomenon from a microsociological perspective, looking at individual characteristics of participants, its broader relationship to class-based changes in nature of work during the neoliberal period has not been thoroughly investigated. This article theorizes the rise of extreme endurance sports by uniting Marx’s conception of estranged labor under capital in the Economic and Philosophical Manuscripts of 1844 with Pierre Bourdieu’s concept of habitus particularly as articulated within Distinction: A Social Critique of the Judgment of Taste. While injecting macro-level socio economic concerns into the exploration of extreme endurance sports, the author concludes that investigations into the lived experience of participants must continue, but should be united with explorations into the connection between the phenomenology of play and its relationship to class and the changing economic structure.