This thesis theorizes the simulator as the paradigmatic video game text reifying the systemic logic and structuring principles of rationalization, abstraction, and productivity at the core of contemporary capitalism. Deploying the systems-analysis methods of games studies alongside theoretical frameworks of Autonomist Marxism, this intervention proposes a means of working through the entanglements of labor and leisure reified in games that simulate work. This thesis therefore asks, in what ways must we revise the notions of ‘productive’ games when confronted with unremunerated forms of play that nonetheless reproduce, sustain, or calcify the logics of capital? In short, why do we play hard work? Tracing the circuits of capitalism through simulation, this thesis first examine ‘Games of Production’ such as Stardew Valley and Factorio – simulators that crystallize the logic of scientific management and Fordist organizational regimes of totalizing managerial control in the perennially privileged sites of production, the farm and factory. This thesis then follows the flows of capital by interrogating truck simulators as ‘Games of Circulation,’ which simulate a ground-up view of the networks of logistics that sustain the movements and flows of global capitalism. Ultimately, this project aims to show that through the simulation of capitalism’s vast matrix of systems and logics, simulators not only reify the structuring principles of capital, but also serve as optics to chart insurgencies that resist them.