Over the past 70 years, because of their different historical and social contexts, the film industries of China’s three regions, namely mainland China, Taiwan, and the Hong Kong Special Administrative Region (SAR), have exhibited distinct characteristics that grow out of a single cultural root. Based on data from the Internet Movie Database (IMDb), this study investigates how the image of China has spread overseas through cultural products by applying big data analysis and machine learning methods to compare the content, topics, and attitudes toward the image of China disseminated by films originating in these three regions. The results show that the three areas have sought to express their subjectivity during periods of flux and striven to connect with the world in films. The macroscopic analysis of large-scale content allows the exploration of hidden cultural phenomena and compensates for the lack of objectivity of traditional research methods, while understanding embedded historical and cultural contexts of the three regions helps to clarify the regions’ ethnic, cultural, and emotional connections. Therefore, this study has contributed to cultural sociology both in topic and methodology.