This essay takes up the significance of Wittgenstein's philosophy for our understanding of literature (and vice versa) through a comparative reading of the stakes and aims of Kafka's and Wittgenstein's respective circa 1922 puzzle texts “Von den Gleichnissen” (“On Parables”) and the Tractatus Logico-Philosophicus. The essay builds upon the so-called resolute program of Wittgenstein interpretation developed by Cora Diamond, James Conant, and others, bringing its insights to bear on Kafka's perplexing work. The essay explores the ethical weight of these two writers' investment in the philosophical depth of riddles, irony, and parabolic and nonsensical expression as unorthodox modes of indirect instruction about ordinary language and world, the yearning for transcendence, and the failure to achieve it. Both demanding works deal with the ethical difference between “getting” the philosophical import of a story or joke and not getting it in the context of an examination of the relationship (or lack thereof) between the activities and difficulties of everyday life, on the one hand, and those of literary expression and/or spiritual or philosophical teaching, on the other. Both strive to open readers to experience — as revealed through everyday language — by leading us beyond the dichotomy of facticity and transcendence, away from the urge to transcend the limits of language, and toward a recognition of the possibility of seeing our ordinary dealing with things as presenting a face of significance that is at once linguistically meaningful and ethically valuable. The central aim of this discussion of Wittgenstein's Tractatus and “Lecture on Ethics” alongside Kafka's parable is to examine the ways in which Wittgenstein's philosophical outlook, writing, and method (shaped by his general attraction to the Book and book writing as well as by his reading of certain works of literature) are deeply relevant to literary studies, and particularly to our understanding of literary modernism.