This article examines the relationship between Jewish jokes and the development of modern Yiddish literature. Beginning by exploring the central role of humor within the environment of Yiddish-speaking Ashkenazi culture, the article goes on to outline how jokes, especially their orality, have come to be understood as representative elements of that humor. During the formative period of modern Yiddish literature, in the late nineteenth and early twentieth centuries, authors experimented with forms and genres to expand the literature and its expressive potential. Sholem Aleichem, one of that literature’s most famous exponents, used humor as a central component of that expansion. This article concludes with an analysis of how he used the joke as an experimental tool in the development of Yiddish literature.