Tracing key historical junctures from George Town’s founding to the present, this chapter offers an interpretation of its evolution. It examines how the town’s development was fashioned by local, regional, and global forces—first as an East India Company settlement, then as a Crown colony, as British influence expanded across the Malay Peninsula in the late nineteenth century. The analysis considers the impact of the Japanese occupation during the Second World War and the subsequent transition to independence, highlighting the emergence of racial tensions and the introduction of race-based policies that continue to structure Malaysian society. Particular attention is given to the anxieties of the Straits-born Baba Nyonya regarding their political rights and status in the postwar period. The discussion also explores the twin processes of economic modernisation and heritage-driven urban renewal in post-independence Penang, arguing that the rigid ethnicisation of contemporary Malaysian politics does not reflect George Town’s complex historical and contemporary realities. In doing so, the account provides deeper insights into Penang’s multicultural heritage and sociopolitical landscape, reflecting on colonial legacies and the ongoing contestation of identity.