This article explores Japanese artists’ proactive engagement with wartime politics through the formulation of patriotic art associations during the Asia-Pacific War (1937–45). The main foci of this investigation are three artist collectives formed in response to the outbreak of war and the advent of the mass mobilization policy: the Army Art Association (Rikugun Bijutsu Kyōkai), the Women Artists Service Corps (Jōryū Bijutsuka Hōkōtai), and the Art Unit for Promoting the Munitions Industry (Gunju Seisan Bijutsu Suishintai). Although these three collectives were all created under the banner of promoting Japan’s imperialist war, the actual motives behind the foundation of and participation in these patriotic art associations varied to a significant degree, depending on the artists’ political/economic standings, age, gender, and the ever-changing conditions of the war. Carefully contemplating these sociopolitical factors, whether imposed upon or internalized by the artists, illuminates how artists from time to time actively committed to the war effort in order to pursue their own benefits. By closely examining the formulation and activities of these patriotic art associations, this article reveals how the alliances between artists and Japan’s wartime state were formed, not only through top-down control but also as a result of a multilateral reciprocity, thereby exploring how artists played a proactive role in forming the wartime cultural landscape.