Games have played an important role in modern educational methodologies. Beginning with the work of luminaries like Froebel, Montessori, and Dewey and continuing through the Cold War, the counter-culture movement of the 1960s and '70s, and into the present day, shifts in educational practice can be traced historically using the lens of games, where concepts like play, win strategies, cooperation, and engagement figure prominently in curricular structures. The author investigates how games have been discussed in art education literature, linking how the use of games in art educational environments significantly reflects the sociopolitical contexts of the 20th century.