Book 7 looks at Bob Dylan's return to his musical roots as a catalyst to a decade of creative rebirth.

Live performance had gotten stale for Dylan, and he had strongly considered retiring altogether while on an eighteen-month tour with Tom Petty and the Heartbreakers. "My own songs had become strangers to me, I didn't have the skill to touch their raw nerves, couldn't penetrate the surfaces," Dylan recalled in Chronicles. "There was a hollow singing in my heart and I couldn't wait to retire and fold the tent." In Chronicles, Dylan revealed that "it all fell apart" during an outdoor concert in 1987 at the Piazza Grande Locarno in Locarno, Switzerland.

However, Dylan emerged from this creative crisis a few months later rejuvenated. He assembled a new band with G. E. Smith on guitar, Kenny Aaronson on bass, and Christopher Parker on drums for his Interstate 88 Tour, which they kicked off on June 7, 1988, in Concord, California. With the exception of 2020, the start of the global COVID-19 pandemic, Dylan has toured annually to the present day. Although fans have referred to Dylan's schedule since 1988 as the Never Ending Tour, Dylan himself has rejected the sobriquet. Not only have some of his tours been individually named, they have involved a revolving cast of musicians throughout the years.

Among the albums from this period is Down in the Groove, in collaboration with Eric Clapton, guitarist Steve Jones of The Sex Pistols, and bassist Paul Simonon of The Clash. Oh Mercy was released on September 12, 1989, and widely hailed as a return to form. Dylan also joined The Traveling Wilburys alongside George Harrison, Roy Orbison, Tom Petty, and Jeff Lynne.

In 1991, Dylan and Columbia Records issued The Bootleg Series Volumes 1-3 (Rare & Unreleased) 1961-1991, an authorized career-spanning retrospective that merely scratched the surface of the immense trove of unissued music that Dylan had amassed in his thirty years as a recording artist. The Bootleg Series has continued to date, delighting fans and winning critical acclaim with sets devoted to pivotal moments in Dylan's career, including individual albums, tours, and musical periods.

Released on September 30, 1997, Time Out of Mind, Dylan's thirtieth studio album, changed the trajectory of his long career. The critical and popular reappraisal of Dylan's music underscored Dylan's vitality as an artist, especially at a time when few of his contemporaries were making albums that could stand alongside their past triumphs. The album won Dylan his first-ever GRAMMY Award for Album of the Year, and presaged a mid-career resurgence that continues to this day. Yet the success of the album hadn't come from out of the blue; rather, Dylan's touring regimen, the solidification of his backing band, and his re-immersion in his musical roots all set the stage for the work contained on Time Out of Mind.