Even though critically acclaimed as one of New Zealand’s greatest writers, David Ballantyne, a literary figure with considerable skills and coherence of vision, has been disregarded until recently. Likewise, his coming-of-age story, Sydney Bridge Upside Down (1968), has been out of print for thirty years but is called one of the great New Zealand literary masterpieces. While introducing Ballantyne, who is unknown to Korean readers, this paper explores his novel, Sydney Bridge Upside Down, which, set in an abandoned slaughterhouse, describes the strange, unpredictable, and sinister story of a New Zealand boy on the edge of the world. It is narrated by the faux-innocent voice of the pre-adolescent boy, Harry, disguising a series of killings in both a remote country and a busy city in which killing, sexual temptation, and violence are overwhelmingly mingled. Its plot is mysterious, with dreamlike stream of consciousness, a general air of suspicion, and a dark sense of humor. By focusing on his fairy tale madness and untamed childhood fantasy related to women in a forbidden and dangerous place, this paper characterizes the extremely troubled young Harry with his burgeoning sexuality and jealousy as a heroic monster who tries to save “a beautiful short-sighted girl from being captured by a hairy monster,” referring to his Mum escaping the country and his cousin Catherine escaping the city.