Throughout the developed world, in which digital media have achieved a ubiquitous status for many people, games have become an exemplary cultural form that serves as a prominent metaphor of everyday competition and success. This essay explores gamification—a term that derives from behavioral economics and refers to the use of game mechanics in traditionally nongame activities—as a form that economic, social, and cultural life increasingly takes in the present. After exploring how the gamified world of the early twenty-first century departs dramatically from a society oriented around the production of what Guy Debord called “spectacles,” I turn to three recent digital games that problematize gamification: SPENT (2011), Third World Farmer (2006), and Thresholdland (2010). Each of these games repurposes a different digital game genre (the role-playing game, the construction and management simulation game, and the transmedia game) and tackles a different topic (poverty and homelessness in the United States, underdevelopment of the Third World, and immigration struggles in Europe). Despite these differences, they all actively challenge the victory-oriented nature of gamification while critically foregrounding the structural failure and mass loss perpetuated by systems of contemporary capitalism. In the conclusion, the essay explores play as a precarious, uncertain, but also transformative relation that might complicate the gamified elements (points, badges, and reputation systems) that so often organize games and social practices in the early twenty-first century.