In this paper, we discuss, from both biological and cultural perspectives, the ancient human-plant liaison that gave rise to Near Eastern agriculture. We explain the biological aspects of Near Eastern plant domestication by a comparative analysis of legume vs. cereal crop evolution. This comparison is illustrated by the natural distribution, ecological affinity, physiology, population structure, floral biology, growth habit, plant stature, seed dispersal mode, and seed dormancy of both wild and domesticated plants of these crop groups. We discuss the differences between Near Eastern legumes and cereals with regard to each of the above aspects, and we highlight the relevance of these differences with regard to Neolithic decision-making, adoption for farming, and subsequent evolution under domestication. We reached the following conclusions: (1) Near Eastern legumes underwent different evolutionary trajectories under domestication as compared with their companion cereals, despite apparent similarities between selection under domestication of both crop groups. (2) Careful comparison of pea, lentil, and chickpea shows that each of the Near Eastern legume crops has a unique evolutionary history in its own right, and this also holds true for the cereal crops. (3) The evolutionary history of each of the Near Eastern crops, prior to as well as after domestication, is well-reflected in its adaptation profile in present-day cropping systems, which determines each crop's relative economic importance in different world regions (e.g., chickpea is a major pulse in the Indian subcontinent, and pea is a more important crop in temperate regions, while barley has the widest adaptation, extending from high-latitude temperate regions to semi-arid Mediterranean systems). (4) Ancient choice-making as reflected in the founder crops repertoire, involved nutritional considerations that may have outweighed grain yield per area and/or time unit criteria.