The history of the ethnic Chinese in Southeast Asia has been one of trials, tribulations, as well as of economic success amidst varying degrees of discrimination and acceptance in their adopted countries. Beginning with the Southern Song dynasty (1127–1279), China's interest towards Nanyang (South Seas) reached its high point during the reign of Ming emperor Zhu Di. Commerce and trading activity in the region and the ambitious quest for an enlarged suzerainty saw eunuch Admiral Zheng He's (Cheng Ho's) famous voyages to the region. The subsequent arrival of the European colonialists, starting with the Portuguese, led to rapid economic expansion and an influx of Chinese and Indian migrant labour to service the growing demands for labour and entrepreneurship in the colonial lands, a phenomenon that reached its peak in the late nineteenth and early twentieth centuries and was responsible for much of the heterogeneity of Malaysia and Singapore today.

Thus, the geopolitical-ethnic uniqueness of Singapore is not a recent development. The British were conscious of its geopolitical centrality despite the stereotypical description of Singapore as a “sleepy Malay fishing village”. In a matter of decades from Sir Thomas Stamford Raffles' founding in 1819, Singapore was transformed from an indigenous Malay enclave into a Chinese-majority entity. Its rise as an important entrepôt coincided with the themes of discrimination, ethnic violence, and pogroms against the ethnic Chinese in other parts of Southeast Asia. The constant challenge faced by naturalized ethnic Chinese in Southeast Asia was, and remains, to maintain their ethnic identity without doubts being cast on their commitment to the newly adopted homelands and the region. Similarly, Singapore's Chinese exceptionalism needs to be managed within the intricacies of ethnic relations in a multi-ethnic society and the latent regional geopolitical sensitivities against the backdrop of the putative rise of the regional hegemon, China.

In this chapter, Singaporean “Chineseness” refers to the trend in which increasing importance and prominence is placed — in form, if not in substance — on Chinese language and culture within political, economic, and socio-cultural discourse in Singapore.