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In the opening lines of his book The Tales of Rabbi Nachman, Martin Buber positions Rabbi Nachman as the final link in a chain of tradition that has “now” broken. Rabbi Nachman stands at the far edge of the break that was constitutive of Buber’s own modernity. Hebrew literary historiography has largely embraced the narrative of a break between traditionalist and secular writing, and has seen this break as constitutive of the modernity of “secular” Hebrew writing. And yet, every major “secular” participant in the production of “modern” Hebrew and Yiddish literature has engaged in some way with the tales of Rabbi Nachman. From I. L. Peretz to S. Y. Avramovitch, from Y. H. Brenner to S. Y. Agnon, from Der Nister to Bashevis-Singer and many others, the widespread engagement with the tales of Rabbi Nachman cannot be dismissed. Nor can it easily be reconciled with the divisions purportedly constituted by an imagined break between traditional and modern—or religious and secular—writing. The present paper will begin by discussing the imagined break and its historiographical function. It will then proceed to explore the investment of several major writers—Peretz, Avramovitch, Brenner—in the literary activity of Rabbi Nachman by discussing the literary characters of the Talush, the Madman and the Hassid in their writing. More than to argue for the “modernity” of Rabbi Nachman’s tales, it will seek to problematize the notion of a “literary break” and ask questions about the relation between Jewish literature and Jewish modernity.