This chapter explores short American fictions that are like jokes, drawing on Sigmund Freud’s contrast between the “tendentious” joke, which generates “pleasure by lifting suppressions and repressions,” and “innocent” humor, its pleasure based on “the liberation of nonsense.” In opposition to ideas of the classical American short story as a compact vehicle of epiphany, it argues for a countertradition of short fiction of “innocent” comedy, which features the linguistic slapstick generated by language learning and exposes the instability of language. It frames the immigrant Leo Rosten as an inheritor of Mark Twain, Ambrose Bierce, and O. Henry, all of whom draw on lexicography and language learning to explore the “innocent” humor of unstable language. Like Boris Eikhenbaum in his description of O. Henry, Rosten’s best-known protagonist, the English-language student Hyman Kaplan, asserts that Russian Jews such as himself are especially attuned to the comic potential of English.