When God created the world, so it is said, he sent out an angel with a bag of foolish souls with instructions to distribute them equally all over the world—one fool per town. But the angel’s bag broke and all the souls spilled out onto the same spot. They built a settlement where they landed: the town is known as Chelm. The collected tales of these fools, or “wise men,” of Chelm constitute the best-known folktale tradition of the Jews of eastern Europe. This tradition includes a sprawling repertoire of stories about the alleged intellectual limitations of the members of this old and important Jewish community. Chelm did not make its debut in the role of the foolish shtetl par excellence until late in the nineteenth century. Since then, however, the town has led a double life—as a real city in eastern Poland and as an imaginary place onto which questions of Jewish identity, community, and history have been projected. How the Wise Men Got to Chelm is the first in-depth study of Chelm literature and its relationship to its literary precursors. By placing literary Chelm and its “foolish” antecedents in a broader historical context, it shows how they have functioned for over three hundred years as models of society, somewhere between utopia and dystopia. These imaginary foolish towns have enabled writers both to entertain and highlight a variety of societal problems, a function that literary Chelm continues to fulfill in Jewish literature to this day.