As major Asian trading centres and former British colonies, Singapore and Hong Kong inevitably have parallel histories. Although their destinies diverged in the latter part of the twentieth century, comparisons between the two places are useful in developing an understanding of the historical circumstances of each city, and also in developing regional perspectives. The burden of the present article lies in three arguments. First, while the Japanese occupation is often seen as a climactic event in Asian history that destroyed the colonial world and set in motion the transition to independence, the economic policies that defined the post-war era were initiated by colonial regimes during the 1930s and continued by nationalist governments after 1945. Second, the political trajectories followed by Singapore and Hong Kong in the first post-war decades were largely determined by unanticipated developments relating to the cold war, and did not follow logically from the situation that existed in the 1930s, or even when the war ended in August 1945. Third, while both places were seen as colonial relics in post-war Southeast Asia and had to contend with nationalist policies that were incompatible with their social make-up and business practices, efforts to assimilate them within national states were unsuccessful, and they continued to flourish as global city states.