China, Hong Kong, and Taiwan have long been crucibles for cross-cultural encounters between Chinese and Western cultures. They have different political ecologies (in terms of their relative levels of democracy), and Hong Kong and Taiwan have different relationships with China. These two factors have affected the meaning of ‘home country’ or ‘Chineseness’, and therefore the promotion of national identity and nationalism in education and music education are different in these three Chinese societies. The changes in the school music education systems of Mainland China, Taiwan, and Hong Kong are a response to social transitions in Greater China in relation to development and governance across the region. These societies’ ‘Chineseness’ has been described as a potentially unifying regional identity that can be counterposed against Westernization. It should be noted that Hong Kong society was built on British foundations and adopted English and Western values, even though the locals are ethnic Chinese. Though Taiwan is significantly Chinese, Chinese nationalism in Taiwan continues to change, and school education has attempted to re-imagine Taiwan in a new context of Taiwanese consciousness and Taiwanese ethnicity in its semiotic dimension. Thus, the theme of ‘Greater China’ or ‘Chineseness’ in the imaginary region has been the dilemma in the possible discursive associations that arise from the continuing transformation of school music in response to the recent political and sociocultural developments in these three Chinese territories.