The 1965 Merchant Ivory Productions film Shakespeare Wallah depicts a British theatrical troupe performing Shakespeare in post-independence India. Although the film situates the viewer's sympathy with the British members of the troupe, the filmmakers also present the troupe ironically, showing how they are floundering and nostalgic in the face of a liberated India. The film is made more complex by the fact that the actors playing the central roles were themselves members of the Shakespeareana troupe that had actually toured Shakespearean productions across India both before and after independence; several of the actors were essentially playing themselves. The film and its characters—both the real and fictionalized versions—thus adopt a highly ambivalent attitude toward postcolonialism and the role of Shakespeare in India. This article begins with an overview of interculturalism and cultural imperialism as they relate to Shakespeare in Asia and then explores how these different modes of postcolonial cross-cultural interaction are depicted and performed in this fascinating film.