This chapter sheds light on the complex cinematic milieu in Korea during the period of Japanese rule (1910-45). First, in a case study of Sweet Dream (1936), a “co-production” between the Chosŏn Film Company and the Kyŏngsŏng Film Studio, I investigate how filmmakers in colonial Korea used entertaining “message” films to engage with the “lady of leisure” figure popular in contemporary Hollywood films, while also critiquing the “modern girl” narrative. Challenging contemporary racial stereotypes and eugenic theories, Sweet Dream is one of many collaborative productions that profited from the combination of Korean production crews and Japanese financiers, who controlled a large slice of the East Asian film industry. Second, a case study of “rehabilitation” screenings of the Hollywood film Les Misérables (1935) by the P'yŏngyang Yuhyang-hoe illustrates how government-backed benevolent organizations assisted discharged prison inmates to reintegrate into society. The production and exhibition of Sweet Dream and Les Misérables respectively show how the colonial authorities valued films that contained civic conventions (such as traffic rules and public orderliness) as well as social assimilation. Hence, during this period a wide range of films were utilized to further Japan’s modernizing agenda for Korea and to promote its assimilationist ideology to Koreans. Both Sweet Dream and Twentieth Century Pictures’ Les Misérables are representative films in the development of the colonial Korean cinema insofar as they encapsulate key features of the industry as well as reflect the larger social and cultural developments of the time, including the clash of cultures and the theme of modernity versus tradition.