The ties that bind the Greco-Roman and Hebrew cultures together are strong and convoluted, from as early as their beginnings in ancient times. This chapter deals with the encounter of modern Hebrew poetry with the Greco-Roman classical tradition, situating it in the polarized relations between the two cultures, as well as in their close and symbiotic interactions. Complex historical residues played a role in the relatively belated reception of Greco-Roman classical elements in modern Hebrew literature. And while Greco-Roman elements contributed to the shaping of Hebrew literature as part of modern European culture, they were not integrated deeply into it. It was only after the Second World War that a window of opportunity for a common cross-cultural destiny opened up, when Hebrew writers saw the shared platform of the two cultures as a bulwark against fascism. At the same time, the belatedness in the reception of elements of the Greco-Roman classical tradition in Hebrew poetry prevented them from being “eroded”, as it were, by the Biblical corpus (the main point of reference of Hebrew literature) – by becoming, for example, objects of irony or parody.