A meaningful theory of digital labor and play cannot simply point out their inseparability, but rather must consider how the two practices reproduce and reveal one another in paradoxical ways. In this chapter, Benzon considers two recent cultural texts—Douglas Coupland’s novel jPod and the smartphone art game i-mine—to offer such a theory. Repeatedly doubling work and play back upon one another, these texts offer an immanent critique of the digital economy through form: moments of seeming authorial play in Coupland’s novel instead make the text feel like work, establishing boredom and banality as operational conditions for reading. In i-mine, the boredom of the game’s haptic work serves as a procedural critique of labor exploitation within digital industrial production. Both texts, then, turn to boredom as an avenue of engagement, a crux between work and play in the digital economy. Tracing how these texts implicate the reader/player within the paradoxes of digital labor, Benzon suggests that the boredom that defines both work and play might serve as a critical lens through which to reveal complex interdependencies between devices, bodies, corporations, and infrastructures across the global digital economy.