This thesis builds upon the existing fields of speculative and critical design to consider how games can foster critical reflection. It takes a bi-directional approach, exploring manifestations of criticality for players and their retellings (when a player tells others a narrative or anecdote about their experiences of play), as well as criticality in a research-creation project called MENU NEW GAME+ (MNG+)—a game that tasks players with exploring main menus for games that do not, and will not, exist. First, the process of developing MNG+ is explained, and ‘menuization’ (the creation of game menus) is posited as a method for bringing the findings of speculative and critical design practices into the realm of game design (speculative play); second, the idea of a critical game retelling is explicated, and such retellings are argued to be an underutilized resource for game designers and academics to explore both game design and player experiences. From both sides (player and designer), concrete manifestations of criticality are explored and explained through the lens of creating breakdown situations that do not abandon the notion of usability.