In popular culture, the memory of war is often appropriated through a process of trivialization, diminishing war so that it becomes familiar and desirable rather than ominous and frightening. With a focus on the Swedish author and illustrator Ossian Elgström (1883–1950), the article suggests that the process of trivialization is central to the understanding of play in boy’s literature published at the beginning of the twentieth century. Through the fictional representation of children playing at war, the patriotic soldier not only becomes a quintessentialfigure of masculinity. The play elements trivialize war and uphold a specific form of hegemonic masculinity characterized by courage and honor as well ashumor, fair play and camaraderie in contrast to the adult world. Both narrative structure and shifting of focalization prove to be important in relation to theprocess of trivialization and the imagining of boyhood masculinity in Elgström’s books. In connection with the war play motif, the article ends with a discussionof Elgström’s interwar engagement in national socialist activities.