This essay presents an analysis of a particular rabbinic parable tradition, in an attempt to chart its diachronic development as a literary form in traditional Jewish lore. The parables under consideration belong to the grouping identified as “Parables of the King.” These are stories with a royal hero. In the examples discussed here, ridiculous conditions are presented as prerequisites for participation in a royal banquet. This motif derives from a pronounced eschatological context; however, new narrative elements were added at different chronological stages to the parallel versions of the parable, changing significantly its original theological setting. This paper is a study of this literary tradition, in light of a corresponding NT parabolic tradition and of its link to a tradition known from the apocryphal Apocryphon of Ezekiel. The article aims to establish the mode of evolution of the literary form of the parable from the hypothetical ancient Jewish homiletic tradition, as preserved in the NT, to its manifestation in rabbinic literature. At the same time, the article tracks the history of the eschatological idea behind the parable.