Sixteenth-century literature witnessed a remarkable shift from the courtly sphere to the lives of burghers, innkeepers, lansquenets, peasants, and workers. In the countless Schwänke (jest narratives) published during this period, we are both entertained and instructed by listening to what ordinary people said to each other, what they fought over, and what mistakes they might have made in their social relationships, often leading to facetious situations meant to provoke our laughter. One of the most popular authors of this genre was Georg/Jörg Wickram, who effectively created the model collection with his Rollwagenbüchlein (1555), a work that runs almost parallel—but in prose—to Chaucer’s much earlier Canterbury Tales (ca. 1400). Wickram’s text primarily addressed the typical representatives of early modern society who were well-educated and wealthy city dwellers. Many other writers later followed Wickram’s literary concept in crafting their jest narratives. This study closely examines the broad spectrum of individuals who appeared in the literary framework and served as the butt of the jokes. Such an approach makes it possible to understand how the reading audience viewed foolish peasants, clerics, aristocrats, prostitutes, merchants, physicians, or craftsmen who populated early modern cities and the countryside. In this sense, the Rollwagenbüchlein acts as a literary mirror of early modern society. While Sebastian Brant, in his famous Narrenschiff (1494), had ridiculed virtually everyone, Wickram offered satirical narratives on the individuals populating his world (primarily Southwestern Germany).