The authors look at Caillois’ reflections on the dichotomy between work and leisure in relation to Marxism, whose dialectics are shown to influence the milieu under which Caillois developed his ideas. The contribution interrogates this labor/play dialectic while looking at recent literature on games being produced within the current capitalist and neoliberal system, focusing on phenomena like “playbour” and on key elements discussed in these theories, from the affordances and limitations of technology to the immaterial technological tools used by gamers and game makers. The article argues that looking at Caillois in relation to Marxism would provide an interesting critical perspective, one that has been underexplored by current approaches. The authors note that contemporary concerns on capitalism and games are far from being at odds with Caillois’ distinction between labur and play and suggest that the influence of Marxism on Caillois’ writings would provide an interesting terrain of further discussion.