This study is centred on the Four Seas Pictorial (1951–1956) published by the U.S. Information Service in Hong Kong, and investigates how the USIS used the Four Seas Pictorial as propaganda to seek resonance from readers in Southeast Asia and shape their imagination of the free world. The study collects documents on the Four Seas Pictorial from the U.S. National Archives and Records Administration to research a publication that was considered a sister product of World Today, as well as a pictorial news magazine issued by the Hong Kong USIS for Southeast Asian readers, and the first pictorial in Western-aligned Southeast Asia. Through research on the Four Seas Pictorial, aside from the pictorial record and ideological formation functions of the pictures, we also find that “politics” within the “entertainment” was characterized by mass appeal and commercialization. The objective was to realize the cultural propaganda objectives of American power in a more economically rational way in order to win the support from more readers in the free world of the United States and Free China. In addition, through the editing of the Four Seas Pictorial, we can see the possible changes in American power through its local intermediaries. The overall direction of the United States was to maintain the correct ideology, but details, including the form it should take, were decided by local intermediaries. Finally, the study reflects on the possibility of a history of Hong Kong pictorials. In existing research on late Qing pictorials, we can find pictorials produced in Hong Kong. In addition to the influence of the Chinese pictorial tradition, we also have publications such as the Four Seas Pictorial, which has been regarded as the Hong Kong version of Life, showing both Shanghai and American influences in the development of Hong Kong pictorials.