The purpose of this paper is to examine the image of the city as represented and conceptualized in the works of prominent modern Arab poets, mainly since the 1950s. In this article, I will argue that the attitude of these modernists toward the city is characterized by a unique ambivalence. On the one hand, many of them (particularly those who migrated from provincial towns and rural areas to a capital city) unequivocally depict the city or metropolis as a harsh and cruel prison. On the other hand, these same poets recognize the immeasurable possibilites and the immense cultural space the big city offers its inhabitants, especially its poets and artists. Accordingly, a more incisive reading of their works reveals that modern Arab poets are also enthralled and captivated by the modern city. They feel that they have to put up with the metropolis, awe inspiring as it may be, distant from the "firsts sky" as it may be, because it allows them to confront paradox and incongruity, thus eliciting creativity. Therefore, as far as most Arab modernist poets are concerned, having been uprooted from their home village has put them face to face with "the other". In their eyes, it is exactly this challenge to their comfortable and somewhat stolid existence that propels them to the forefront of artistic creation.