This chapter examines how a variety of writers have strategically manipulated reductive ‘Orientalist’ strategies of representation across quite different texts and historical moments. It begins with a discussion of the life and works of Sake Dean Mahomed, Travels of Dean Mahomet (1794) and Shampooing or Benefits Resulting (1822), the first Indian to write in English and publish in Britain. It also draws briefly on the letters of Ignatius Sancho to show how both writers similarly exploit and play on the concept of ‘exoticisation’ to create different personas which aid their passage through British culture. The chapter highlights how the seductive trope of the ‘Oriental’ and the ‘exotic’ persisted in the reception of influential twentieth-century Indian poets who were both prominent in British literary culture, Rabindranath Tagore and Sarojini Naidu. The chapter concludes with an analysis of Hanif Kureishi’s much later invention of Karim Amir and his father in The Buddha of Suburbia (1990), Englishmen ‘almost’ (Kureishi), to show how all these writers deliberately straddle multiple positions and use dualities, the ability to look in two directions at once, to their own advantage.