The popularity, reputation, and influence of George Orwell at home and abroad remain phenomenal more than sixty years after his death. In comparison with other foreign literary masters or popular writers, Orwell’s reception in Taiwan, with the many different translations and paratexts of Nineteen Eighty-Four and Animal Farm, has been exceptionally warm, long-standing, even “Orwellian.” This phenomenon has much to do with Taiwan’s unique historical background, especially its geopolitical context and ideological position in the Cold War. If translation is an afterlife, as Walter Benjamin’s famous metaphor goes, we cannot but wonder about Orwell’s afterlife in Taiwan—a self-proclaimed bastion of anti-communism during the Cold War and a unique country in the Sinophone world. This paper mainly focuses on the translations and representations of Orwell’s Nineteen Eighty-Four and Animal Farm in Taiwan over the past six decades. Whereas the former has often been read as yuyen, meaning both “prophecy” and “allegory,” the latter has been read as political fable and children’s literature, thus extending the author’s readership to schoolchildren. There have been two periods of particularly heightened interest in Orwell: one in the 1950s and the other around 1984. In addition to tracing representative translations of Nineteen Eighty-Four and Animal Farm over the years, this paper discusses how Orwell and his works have been represented by translators, publishers, writers, critics, and intellectuals alike. Taken together, they have made Orwell one of the most popular and respected foreign writers in Taiwan.