My essay examines Bob Dylan’s relation to sound recording, still a neglected topic even with the recent explosion of scholarship on the legendary singer-songwriter. Drawing on historical accounts of Dylan and his career, as well as recent histories of studio recording, I trace the artist’s mercurial relation to record making as evidenced in his turbulent encounters with various record producers. My chief focus is on Dylan’s account of his late 1980s creative crisis in his 2004 memoir Chronicles: Volume 1, which I argue also provides a condensed account of the songwriter’s philosophy of sound recording.