With a career that’s lasted over 60 years,Bob Dylanhas had plenty of ups and downs and, after a period of creative struggles, managed to release one of his greatest albums more than three decades into it. While many new listeners will discover Dylan for the first time throughTimothée Chalamet’s excellent performance in the biopicA Complete Unknown, longtime fans know that there’s a lot more to the singer-songwriter than his hectic days in the 1960s. Even though Bob has had several artistic downturns, what’s impressive is that he has always found a way to renew himself creatively.

From Dylan’s country crooning on divisive albums likeNashville Skylineto the mixed response towardSelf Portraitin the early 1970s, even this future Nobel Prize winner’s heyday alienated some of his listeners. This willingness to experiment with his style and sound was also part of what madeDylan’s albumsso great, as even when audiences didn’t understand his work, he followed his own path and wasn’t influenced by others' expectations. AlthoughBob has plenty of albums hailed as his comeback, none of them reached the magnificent power of what he achieved with his 1997 record.

Bob Dylan - Time Out of Mind (1997)

Bob Dylan Struggled In The 1980s And 1990s

Dylan struggled to fit in among the synth-pop stylings and grunge aesthetic of these decades

The 1980s and early 1990s were tough times for Dylan fans as, although many appreciated his work during this era, he struggled to find mainstream commercial success. The early 1980s were a controversial time for Dylan, as he became a born again Christian and went on long, biblical rants at his live shows where he refused to play any music that didn’t spread the word of God. WhileBob moved away from his gospel phase on albums like 1984’sInfidels, the fundamentalism with which he spread his religious message alienated much of his core fan base.

Dylan’s albumsKnocked Out Loaded(1986) andDown in the Groove(1988) were both commercial failures that received near-unanimous negative reviews. Critics at the time were starting to dismiss the singer as a relic of a bygone era who was no longer relevant within the polished, overproduced musical landscape of pop and rock at the time.

Bob Dylan playing the harmonica for the cover of his 2023 album Shadow Kingdom.

Bob’s time with the supergroup the Traveling Wilburys, where he teamed up with legends like George Harrison, Tom Petty, Jeff Lynne, and Roy Orbison, received acclaim, and albums like 1989’sOh Mercyfelt like a return to form. However, the entire 1980s were a shaky time for the singer, and the 1990s started rough with the albumUnder the Red Skyopening with “Wiggle Wiggle,” a song commonly ranked among his worst compositions. After returning to his folk music roots with two cover albums of acoustic renditions of traditional songs, Dylan was primed for a true comeback of epic proportions.

Time Out Of Mind Was A Huge Comeback For Bob Dylan

Dylan found his voice once again and emerged with a brand-new style

Dylan reunited with theOh Mercyproducer Daniel Lanois for his major comeback record,Time Out of Mind.While Bob has reinvented himself plenty of times, something about this album was different, as the haunting blues rock sound and deeply introspective lyricism felt like a swansong for Dylan’s career and almost like a farewell album. Opening with the cynical anti-love song “Love Sick,” the youthful energy of Dylan’s voice in the 1960s was replaced with a rugged and aged delivery that signaled a lifetime of hardship in every line.

Dylan had been hospitalized with a near-fatal heart infection shortly before the album’s release.

Time Out of Mindwas an extraordinary record whose quality matched Dylan’s work during the 1960s, as tracks like “Standing in the Doorway,” “Tryin' to Get to Heaven,” and “Not Dark Yet” addressed the singer’s mortality head-on. These existentialist themes were bolstered by the fact that Dylan had been hospitalized with a near-fatal heart infection shortly before the album’s release (viaLA Times), as fans confronted the harsh truth that the singer may not be around forever. Closing out with the ethereal masterpiece that was the 16-minute epic “Highlands,”Time Out of Mindwas one of Dylan’s greatest achievements.

What Bob Dylan Did After His Comeback

Dylan has kept very busy in the years since Time Out of Mind

As an undeniable return to form for Dylan,Time Out of Mindwas just the beginning of a late-career resurgence that continues to this day. Bob kickstarted the 21st century with a bang, as in 2001, he won an Academy Award for Best Original Song for “Things Have Changed,” written for the filmWonder Boys. This was quickly followed up with the astounding album “Love and Theft,” a record that proved his comeback was not just a once-off as he further developed his older blues rock style and infused it with fun-filled Americana, country, and roots influences.

WhileTime Out of Mindmay have sounded like a farewell in 1997, Bob was only getting started as he released more acclaimed studio albums likeModern Times,Together Through Life, andTempest. The release of Dylan’s 2004 memoir,Chronicles, also peeled back the curtain on the notoriously reclusive singer’s personal and professional life. Even thoughDylan is now in his 80s, the fact that his most recent record of original material,Rough and Rowdy Ways, has been dubbed by many as one of his greatest albums showcases just how well and truly he bounced back from his creative struggles.

Time Out Of Mind Is Still An All-Time Great Bob Dylan Album

Dylan achieved something special with his 30th studio album

With a discography as vast as Dylan’s, it can be daunting for those unfamiliar with his later work to decide what records to check out, althoughTime Out of Mindwill always be a solid choice. The success of this record has even extended beyond Dylan himself, as the track“Make You Feel My Love” has been performed by hundreds of other artistsand was famously the only cover song on Adele’s multi-platinum debut album,19. The song has managed to transcend Dylan’s legacy and become a modern standard in the 21st century.

The appeal ofTime Out of Mindhas not diminished in the decades since its release, and in 2023, fans got to hear the record in a new light when it was the subject of Dylan’s long-running compilation series.The Bootleg Series Vol. 17: Fragments – Time Out of Mind Sessionsfeatured a remix of the original album, outtakes, alternate versions, and live recordings, which provided new insight into how Dylan painstakingly discovered his new voice on the record. As a late-career masterpiece from a living legend,Time Out of Mindis theBob Dylanalbum that just keeps giving.