This article traces the representational-symbolic evolution of Jerusalem in poetry by juxtaposing the yearnful exhilaration of Medieval Spain’s Judah Halevi with the much more somber exasperation of modern Israel’s Yehuda Amichai. The narrative charts the shift from the biblically evocative to the everyday mundanity and profanity with the fulfilling of an ancient collective dream. More importantly, the article attempts to examine the various modes of representation ascribed to Jerusalem as well as the mystically irresistible pull of a city that, like none other, has been so intensely portrayed, sacralised and desacralised in literature.