The word "funny" is examined as it is used throughout Selvadurai's Funny Boy (1994) from the early chapters describing the family's domestic life, to the ways in which language dominating public and textual discourses is rendered funny. Through an examination of the multivalent meanings of the words "funny" and "tendencies" in the novel, its intertextual references, and allusions to British canonical literature, this paper explores how the novel's "critical funniness" negotiates such forces as imperialism and nationalism, seemingly stabilizing, but also violent and castrating. Critical funniness poses challenges to the history of British colonialism that frames modern Sri Lanka. This paper shows how the text of Selvadurai's novel resists the essentializing discourses implied in the country's national and sexual ideologies.