Pearl of the Orient and Below the Lion Rock have emerged as Cantopop representing Hong Kong since the late twentieth century. However, their depictions of the city do not capture how popular music constructed diversified ideas of Hong Kong. This chapter examines the transregional origins of Hong Kong’s popular music industry from the 1950s onwards and investigates how it depicted the city across borders. It begins with the transregional origins of Hong Kong Cantopop during the 1950s–1970s, emphasising the city’s image among Chinese communities in Southeast Asia. The next section focuses on the construction of Hong Kong Chineseness. It examines how various songs in the 1980s, such as The Brave Chinese by Liza Wang and True Heart by Anita Mui, presented the city and its China-oriented sentiments to Chinese overseas. The final section investigates the diverse interpretations of Hong Kong identities in Cantopop since the 1990s. It shows how multiple ideas of Hong Kong emerged across generations and regions. Overall, this chapter reveals how Cantopop constructed global, Chinese, and local ideas of Hong Kong. It proposes a transregional perspective that enables a more comprehensive understanding of Cantopop as a global popular music genre originating from East and Southeast Asia.