Due to its geographical position, the Anatolian plateau has always been considered as a bridge in transmitting cultural formations that originated in the Near East to southeastern Europe and to the Aegean. Such a standpoint downgrades the role played by the Anatolian plateau to a transit route between the East and the West, overlooking its distinct structure. It seems that the main bias is in considering the Anatolian plateau as a single cultural unit, ignoring the multifarious nature of its structure. The role the Anatolian plateau played between the ‘East’ and the ‘West’ was much more complex and multi-facetted than assumed, even at times hampering all interaction. Yet another bias is considering Anatolia, in spite of its geographic extent, as the dividing line in defining the boundary between the East and the West. However, it is evident that the geographic limits of the peninsula do not necessarily correspond with the cultural entities. Thus, for example, while the cultural boundary separating the East and the West was somewhere in between the Aegean littoral and the central plateau during the Neolithic period, later it shifted considerably in both directions. On the other hand, through the earlier part of the Chalcolithic period, the extent of the Taurus mountains marks the dividing line between the Near Eastern and Anatolia-Balkan cultural formative zones, which by the Late Chalcolithic period moved much further to the west, up to the Marmara region, the Sea of Marmara then acting as a cultural barrier. Presented here is a conspectus of the recent picture on changing cultural boundaries through the Neolithic to the Early Bronze Age.