This theoretical inquiry explores how prison-themed video games embody gendered stereotypes about prison and how these portrayals more broadly represent gendered representations serving to create a double-masculinization effect through intersecting masculine gaming cultures and masculinized assumptions about prison. Here, we form conceptual linkages between literature on gaming and gender, prison and gender, and two prior studies on prison-themed video games. Although we draw on past research, the primary intent of this inquiry is to serve as a review of the extant literature as it relates to an emerging area of research (i.e., gender- and prison-themed video games). We consider why such portrayals are important to the current discourse regarding gender in games, and in what ways inclusion in this conversation could create more comprehensive and critical outcomes in the future direction of game development, as well as the possibility for games to engage the public regarding traditionally gendered institutions.