Born in Muar, Malaysia to a schoolteacher and housewife, Chiang came to Singapore at the age of 11 and attended the Anglo-Chinese School, where he was placed in the care of his eldest brother Dr Chiang Hai Ding. He is the youngest of seven siblings, including an adopted younger sister. As a child, he made frequent visits to the cinema, and developed a taste for the Hong Kong classics of the 1960s.