Since their inception in the 1960s as hacker-fueled experiments created on supercomputers designed for Cold War battle simulations, video games have always straddled the realms of work and play insofar as the first game developers used highly complex machines of industry to create programs that served no immediate utilitarian purpose. In the following decades, blurring the line between work and play would become a common feature of many contemporary knowledge-based economies. Kelly explores how incorporating game-based projects into humanities courses offers students the foundation for engaging with—and even critiquing—the socioeconomic paradigms that support the conflation of work-with-play. The author’s experiences having students design critical video games in upper-division Critical Writing courses are examined to demonstrate how two primary insights emerge from game-based assignments. First, the process of designing video games exemplifies key characteristics of labor conditions within contemporary knowledge-based economies while also presenting students the opportunity to manipulate these conditions to address relevant social issues. Second, designing critical games allows instructors to reflect upon preconceptions regarding what constitutes the “work” of cultural critique. Finally, the author also offers an interpretive framework for designing new classroom experiences that resonate with the cultural, economic, and technological trends students face in the workplace.