1819 represents a highly charged moment in the Singapore imagination. It marks the birth of our modern city-state, yet it also signals the beginning of our colonisation: the domination of Malay and other Asian cultures by Western powers. Artists have thus responded to the event with widely variant attitudes, ranging from E.W. Jesudason's laudatory Raffles Institution Anthem (c.1963–66) to Isa Kamari's stridently anti-colonial novel, Duka Tuan Bertakhta / 1819 (2011). The prevailing sentiment, however, has been one of playful ambivalence. While accepting the fact of colonisation, artists have rejected a founding myth that glorifies our primary colonist, Sir Stamford Raffles. Instead, we have lampooned him in works like Robert Yeo's play The Eye of History (1991) and Colin Goh's film Talking Cock: The Movie (2002); raised ourselves to the height of his statue in Lee Wen's art event Untitled (Raffles) (2001); highlighted narratives of overlooked figures in the drama of colonisation: William Farquhar, Sophia Raffles, Nonio Clement, Sultan Hussein Shah, Munsyi Abdullah, and Sang Nila Utama. As a cultural researcher and author of the biographical drama The Last Temptation of Stamford Raffles (2008), I shall examine trends behind these divergent representations of our colonisation. I argue that artists have chosen to retell 1819 not as a year of conquest, but as a polymorphous moment of transformative contact between East and West; one in which we may view ourselves, not as the victims of change, but as its agents.