With the perspective of cultural politics, this paper briefly traces how Hong Kong Drama originate from modern Chinese Drama, and merge with the development of Western Drama in the 1960s. In the 1980s, due to the historical problem of "1997," when the sovereignty of Hong Kong would be returned to the People's Republic of China, Hong Kong Drama emerged the sense of localism, and interplayed with its growing subjectivity. In the 1990s, many Hong Kong theatre workers participated in the construction of this subjectivity, which shaped Contemporary Hong Kong dramatic arts, that has been transforming in a fragmentary space, and was characterized by its mixing aesthetics of modernism and post-modernism. This paper illustrates the diversity of Contemporary Hong Kong Drama's aesthetic practice with three theatre workers, namely: Bonnie Chan, Chan Ping Chiu, and Ho Ying Fung. Grounding on self-reflection, they develop three difference approaches, treating theatre as the practice of life, cultural criticism, and an expression of cultural anxiety.