The beginning of the 20th century was marked by a need for a departure, for Britain, from the Victorian sentiments of a bygone era, foremost among which were the soon-to-be antiquated thoughts about her colonies and colonial subjects. Because that moment was quite past the high noon of the British Empire, and yet, it was still significant enough geographically for the sun to never have to set on it, its shadows were looming long and haunting. At this juncture, it became the calling of a few to insist on a restatement of what it meant to be British in the larger context of the world, much of which she still commanded. Some of the more vocal proponents for reconfiguring Britain in the new world context were writers. Among them Rudyard Kipling, Leonard Woolf, and George Orwell are seen as heralds and disseminators of thought prominent from the 1900s till World War II, which resulted in the dismantling of the Empire. Kim, The Village in the Jungle, and Burmese Days, the novels of the respective authors discussed within the following pages, are as much cultural delineations of alterity, as they are portraits of the British entrenched haplessly to their colonial missions. Using Edward Said’s Orientalism and Homi Bhaba’s theory of hybridity, the point of convergence between the British colonial mission and its subjects coupled with the curious tendency to not see it as a confluence can be seen as the wellspring of most perceptions and misperceptions of the “Other” or the Oriental. This “othering” is seen at various degrees in the three novels, and with the exception of Kipling in Kim, Woolf and Orwell in their novels question, rather self-reflexively, the effect on the Briton of this “othering”. While Kipling’s is the rallying cry to a slowly unraveling Empire, Woolf and Orwell raise their voices in dissent understanding that what is unraveling is not just a geographical mandate but also a moral one.