To examine the aesthetics of video games, this paper proposes to consider games as a contemporary multi-media version of the so-called “Denkbild,” or “thought-image,” an experimental genre of philosophical writing employed by members of the Frankfurt School that takes literary snapshots of philosophical, political, and cultural insights that interrupt and challenge the enigmatic form of traditional philosophical thinking. While previous scholarship tends to examine the aesthetics of video game as a homogenous, self-contained genre that can be clearly defined and understood within the framework of a variety of dichotomies, thinking of video game through the lens of the Denkbild allows us to understand the diversity, conditionality, and incommensurability of game as a multimedia aesthetic object. By presenting two snapshots of video game players, the collector and the glitcher, this paper argues that the concept of Denkbild allows us to better understand the relationships between game, gamers, and the socio-political context in terms of unexpected bonds, accidental breakthroughs, and moments of absolute freedom.