I begin this chapter utilizing Walter Benjamin’s theories on storytelling and time in modernity to situate John Wesley Harding’s songs of entreaty in the context of a dissolution of communal time. These songs—“Drifter’s Escape,” “I Am a Lonesome Hobo,” and “Dear Landlord”—establish distinct power relationships. Comprising entreaties of the powerless outsider or the outlaw to those in power, the songs investigate how, during a time when national or communal narratives collapse, such entreaties become rhetorical sites for redrawing or reifying lines of power. Deploying Agamben’s theories on the “bare life” of those consigned to a zone of exclusion, I read “Drifter’s Escape” as an excavation of the legacy of lynching in America. “I Am a Lonesome Hobo,” in these contexts, is read as a revision of the ballads of vagabondage analyzed by Christopher Hill. I ask, in that song, if wisdom inheres in a place outside the law—the location of “honesty” in Dylan’s “Absolutely Sweet Marie”—or if the entreaty, on this album, seeks to redistribute power across lines drawn to exclude. “Dear Landlord” is not read as spiritual allegory or moral disquisition, but, again, as an entreaty questioning such modes of reading or writing.