This chapter looks at the representations of the former British Straits Settlements in English fiction from 1819 to 1950, discussing both British literary works that are located in South East Asia and English-language novels from Singapore and Malaysia. Although over the centuries, Europeans of various nationalities had located, intermarried, and established unique cultures throughout the region, writing in the English language at first remained confined to travel accounts, histories, and some largely anecdotal fiction, mostly by civil servants. English East India Company employees wrote about the region, often weaving anecdotal sketches into their historical, geographical, and cultural descriptions. Civil servant Hugh Clifford and Joseph Conrad are the two most prominent writers of fiction set in the British Straits Settlements during the nineteenth century; they also epitomize two opposing camps in representing the region.