This article begins with an analysis of the two medieval, anonymously published satires Das Lalebuch (1597) and the imitation Die Schiltbürger (1598). These medieval books are discussed from a literary perspective: Das Lalebuch, for example, should be understood as a subtle, satirical (and philosophical) response to Thomas More’s Utopia (1516); Die Schiltbürger demonstrates an initial popularisation or simplification in terms of form and content. In contrast to those assessments, I suggest that at least and especially the Schildbürger stories by Erich Kästner and Otfried Preußler, written in the 1950s, are by no means simply lesser, „degraded“, or „depraved“ reiterations of the original. Although both authors are known for passing on and consolidating our ideas about the Schildbürger, they do not contribute to a history of simplification and trivialisation, but rather make use of the material in pursuit of separate aesthetic concepts.