Time Out Of Mind

Bob Dylan's influence on popular music is incalculable. As a songwriter, he pioneered several different schools of pop songwriting, from confessional singer/songwriter to winding, hallucinatory, stream-of-consciousness narratives. As a vocalist, he broke down the notion that a singer must have a conventionally good voice in order to perform, thereby redefining the vocalist's role in popular music. As a musician, he sparked several genres of pop music, including electrified folk-rock and country-rock. And that just touches on the tip of his achievements. Dylan's force was evident during his height of popularity in the '60s -- the Beatles' shift toward introspective songwriting in the mid-'60s never would have happened without him -- but his influence echoed throughout several subsequent generations, as many of his songs became popular standards and his best albums became undisputed classics of the rock & roll canon. Dylan's influence throughout folk music was equally powerful, and he marks a pivotal turning point in its 20th century evolution, signifying when the genre moved away from traditional songs and toward personal songwriting. Even when his sales declined in the '80s and '90s, Dylan's presence rarely lagged, and his commercial revival in the 2000s proved his staying power.

For a figure of such substantial influence, Dylan came from humble beginnings. Born in Duluth, Minnesota, Bob Dylan (b. Robert Allen Zimmerman, May 24, 1941) was raised in Hibbing, Minnesota, from the age of six. As a child he learned how to play guitar and harmonica, forming a rock & roll band called the Golden Chords when he was in high school. Following his graduation in 1959, he began studying art at the University of Minnesota in Minneapolis. While at college, he began performing folk songs at coffeehouses under the name Bob Dylan, taking his last name from the poet Dylan Thomas. Already inspired by Hank Williams and Woody Guthrie, Dylan began listening to blues while at college, and the genre wove its way into his music. He spent the summer of 1960 in Denver, where he met bluesman Jesse Fuller, the inspiration behind the songwriter's signature harmonica rack and guitar. By the time he returned to Minneapolis in the fall, he had grown substantially as a performer and was determined to become a professional musician.

Dylan made his way to New York City in January of 1961, immediately making a substantial impression on the folk community of Greenwich Village. He began visiting his idol Guthrie in the hospital, where he was slowly dying from Huntington's chorea. Dylan also began performing in coffeehouses, and his rough charisma won him a significant following. In April, he opened for John Lee Hooker at Gerde's Folk City. Five months later, Dylan performed another concert at the venue, which was reviewed positively by Robert Shelton in The New York Times. Columbia A&R man John Hammond sought out Dylan on the strength of the review, and signed the songwriter in the fall of 1961. Hammond produced Dylan's eponymous debut album (released in March 1962), a collection of folk and blues standards that boasted only two original songs. Over the course of 1962, Dylan began to write a large batch of original songs, many of which were political protest songs in the vein of his Greenwich Village contemporaries. These songs were showcased on his second album, The Freewheelin' Bob Dylan. Before its release, Freewheelin' went through several incarnations. Dylan had recorded a rock & roll single, "Mixed Up Confusion," at the end of 1962, but his manager, Albert Grossman, made sure the record was deleted because he wanted to present Dylan as an acoustic folkie. Similarly, several tracks with a full backing band that were recorded for Freewheelin' were scrapped before the album's release. Furthermore, several tracks recorded for the album -- including "Talking John Birch Society Blues" -- were eliminated from the album before its release.

Comprised entirely of original songs, The Freewheelin' Bob Dylan made a huge impact in the U.S. folk community, and many performers began covering songs from the album. Of these, the most significant were Peter, Paul and Mary, who made "Blowin' in the Wind" into a huge pop hit in the summer of 1963 and thereby made Bob Dylan into a recognizable household name. On the strength of Peter, Paul and Mary's cover and his opening gigs for popular folkie Joan Baez, Freewheelin' became a hit in the fall of 1963, climbing to number 23 on the charts. By that point, Baez and Dylan had become romantically involved, and she was beginning to record his songs frequently. Dylan was writing just as fast.

By the time The Times They Are A-Changin' was released in early 1964, Dylan's songwriting had developed far beyond that of his New York peers. Heavily inspired by poets like Arthur Rimbaud and John Keats, his writing took on a more literate and evocative quality. Around the same time, he began to expand his musical boundaries, adding more blues and R&B influences to his songs. Released in the summer of 1964, Another Side of Bob Dylan made these changes evident. However, Dylan was moving faster than his records could indicate. By the end of 1964, he had ended his romantic relationship with Baez and had begun dating a former model named Sara Lowndes, whom he subsequently married. Simultaneously, he gave the Byrds "Mr. Tambourine Man" to record for their debut album. The Byrds gave the song a ringing, electric arrangement, but by the time the single became a hit, Dylan was already exploring his own brand of folk-rock.

Inspired by the British Invasion, particularly the Animals' version of "House of the Rising Sun," Dylan recorded a set of original songs backed by a loud rock & roll band for his next album. While Bringing It All Back Home (March 1965) still had a side of acoustic material, it made clear that Dylan had turned his back on folk music. For the folk audience, the true breaking point arrived a few months after the album's release, when he played the Newport Folk Festival supported by the Paul Butterfield Blues Band. The audience greeted him with vicious derision, but he had already been accepted by the growing rock & roll community. Dylan's spring tour of Britain was the basis for D.A. Pennebaker's documentary Don't Look Back, a film that captures the songwriter's edgy charisma and charm.

Dylan made his breakthrough to the pop audience in the summer of 1965, when "Like a Rolling Stone" became a number two hit. Driven by a circular organ riff and a steady beat, the six-minute single broke the barrier of the three-minute pop single. Dylan became the subject of innumerable articles, and his lyrics became the subject of literary analyses across the U.S. and U.K. Well over 100 artists covered his songs between 1964 and 1966; the Byrds and the Turtles, in particular, had big hits with his compositions. Highway 61 Revisited, his first full-fledged rock & roll album, became a Top Ten hit shortly after its summer 1965 release. "Positively 4th Street" and "Rainy Day Women #12 & 35" became Top Ten hits in the fall of 1965 and spring of 1966, respectively. Following the May 1966 release of the double album Blonde on Blonde, he had sold over ten million records around the world.

During the fall of 1965, Dylan hired the Hawks, formerly Ronnie Hawkins' backing group, as his touring band. the Hawks, who changed their name to the Band in 1968, would become Dylan's most famous backing band, primarily because of their intuitive chemistry and "wild, thin mercury sound," but also because of their British tour in the spring of 1966. The tour was the first time the British had heard the electric Dylan, and their reaction was disagreeable and violent. At the Manchester concert (long mistakenly identified as the show from London's Royal Albert Hall), an audience member called Dylan "Judas," inspiring a positively vicious version of "Like a Rolling Stone" from Dylan and the band. The performance was immortalized on countless bootleg albums (an official release finally surfaced in 1998), and it indicates the intensity of Dylan in the middle of 1966. He had assumed control of Pennebaker's second Dylan documentary, Eat the Document, and was under deadline to complete his book Tarantula, as well as record a new record. Following the British tour, he returned to America.

On July 29, 1966, he was injured in a motorcycle accident outside of his home in Woodstock, New York, suffering injuries to his neck vertebrae and a concussion. Details of the accident remain elusive -- he was reportedly in critical condition for a week and had amnesia -- and some biographers have questioned its severity, but the event was a pivotal turning point in his career. After the accident, Dylan became a recluse, disappearing into his home in Woodstock and raising his family with his wife, Sara. After a few months, he retreated with the Band to a rented house, subsequently dubbed Big Pink, in West Saugerties to record a number of demos. For several months, Dylan and the Band recorded an enormous amount of material, ranging from old folk, country, and blues songs to newly written originals. The songs indicated that Dylan's songwriting had undergone a metamorphosis, becoming streamlined and more direct. Similarly, his music had changed, owing less to traditional rock & roll, and demonstrating heavy country, blues, and traditional folk influences. None of the Big Pink recordings was intended to be released, but tapes from the sessions were circulated by Dylan's music publisher with the intent of generating cover versions. Copies of these tapes, as well as other songs, were available on illegal bootleg albums by the end of the '60s; it was the first time that bootleg copies of unreleased recordings became widely circulated. Portions of the tapes were officially released in 1975 as the double album The Basement Tapes.

While Dylan was in seclusion, rock & roll had become heavier and artier in the wake of the psychedelic revolution. When Dylan returned with John Wesley Harding in December of 1967, its quiet, country ambience was a surprise to the general public, but it was a significant hit, peaking at number two in the U.S. and number one in the U.K. Furthermore, the record arguably became the first significant country-rock record to be released, setting the stage for efforts by the Byrds and the Flying Burrito Brothers later in 1969.

Dylan followed his country inclinations on his next album, 1969's Nashville Skyline, which was recorded in Nashville with several of the country industry's top session men. While the album was a hit, spawning the Top Ten single "Lay Lady Lay," it was criticized in some quarters for uneven material. The mixed reception was the beginning of a full-blown backlash that arrived with the double album Self Portrait. Released early in June of 1970, the album was a hodgepodge of covers, live tracks, re-interpretations, and new songs greeted with negative reviews from all quarters of the press. Dylan followed the album quickly with New Morning, which was hailed as a comeback.

Following the release of New Morning, Dylan began to wander restlessly. He moved back to Greenwich Village, he finally published Tarantula in November of 1970, and he performed at the Concert for Bangladesh in August 1971. During 1972, he began his acting career by playing Alias in Sam Peckinpah's Pat Garrett and Billy the Kid, which was released in 1973. He also wrote the soundtrack for the film, which featured "Knockin' on Heaven's Door," his biggest hit since "Lay Lady Lay." The Pat Garrett soundtrack was the final record released under his Columbia contract before he moved to David Geffen's fledgling Asylum Records. As retaliation, Columbia assembled Dylan, a collection of Self Portrait outtakes, for release at the end of 1973. Dylan only recorded two albums -- including 1974's Planet Waves, coincidentally his first number one album -- before he moved back to Columbia. The Band supported Dylan on Planet Waves and its accompanying tour, which became the most successful tour in rock & roll history; it was captured on 1974's double live album Before the Flood.

Dylan's 1974 tour was the beginning of a comeback culminating with 1975's Blood on the Tracks. Largely inspired by the disintegration of his marriage, Blood on the Tracks was hailed as a return to form by critics and it became his second number one album. After jamming with folkies in Greenwich Village, Dylan decided to launch a gigantic tour, loosely based on traveling medicine shows. Lining up an extensive list of supporting musicians -- including Joan Baez, Joni Mitchell, Ramblin' Jack Elliott, Arlo Guthrie, Mick Ronson, Roger McGuinn, and poet Allen Ginsberg -- Dylan dubbed the tour the Rolling Thunder Revue and set out on the road in the fall of 1975. For the next year, the Rolling Thunder Revue toured on and off, with Dylan filming many of the concerts for a future film. During the tour, Desire was released to considerable acclaim and success, spending five weeks on the top of the charts. Throughout the Rolling Thunder Revue, Dylan showcased "Hurricane," a protest song he had written about boxer Rubin Carter, who had been unjustly imprisoned for murder. The live album Hard Rain was released at the end of the tour. Dylan released Renaldo and Clara, a four-hour film based on the Rolling Thunder tour, to poor reviews in early 1978.

Early in 1978, Dylan set out on another extensive tour, this time backed by a band that resembled a Las Vegas lounge act. The group was featured on the 1978 album Street Legal and the 1979 live album At Budokan. At the conclusion of the tour in late 1978, Dylan announced that he was a born-again Christian, and he launched a series of Christian albums that following summer with Slow Train Coming. Though the reviews were mixed, the album was a success, peaking at number three and going platinum. His supporting tour for Slow Train Coming featured only his new religious material, much to the bafflement of his long-term fans. Two other religious albums -- Saved (1980) and Shot of Love (1981) -- followed, both to poor reviews. In 1982, Dylan traveled to Israel, sparking rumors that his conversion to Christianity was short-lived. He returned to secular recording with 1983's Infidels, which was greeted with favorable reviews.

Dylan returned to performing in 1984, releasing the live album Real Live at the end of the year. Empire Burlesque followed in 1985, but its odd mix of dance tracks and rock & roll won few fans. However, the five-album/triple-disc retrospective box set Biograph appeared that same year to great acclaim. In 1986, Dylan hit the road with Tom Petty & the Heartbreakers for a successful and acclaimed tour, but his album that year, Knocked Out Loaded, was received poorly. The following year, he toured with the Grateful Dead as his backing band; two years later, the souvenir album Dylan & the Dead appeared.

In 1988, Dylan embarked on what became known as "the Never-Ending Tour" -- a constant stream of shows that ran on and off into the late '90s. That same year, he appeared on The Traveling Wilburys, Vol. 1 -- by the supergroup also featuring George Harrison, Roy Orbison, Tom Petty, and Jeff Lynne -- and released his own Down in the Groove, an album largely comprising covers. The Never-Ending Tour received far stronger reviews than Down in the Groove (the Traveling Wilburys album fared much better), but 1989's Oh Mercy was his most acclaimed album since 1975's Blood on the Tracks, due in part to Daniel Lanois' strong production. However, Dylan's 1990 follow-up, Under the Red Sky (issued the same year as the second album by the Traveling Wilburys, now a quartet following the death of Roy Orbison shortly after the release of the Wilburys' first long-player in 1988), was received poorly, especially when compared to the enthusiastic reception for the 1991 box set The Bootleg Series, Vols. 1-3 (Rare & Unreleased), a collection of previously unreleased outtakes and rarities.

For the remainder of the '90s, Dylan divided his time between live concerts, painting, and studio projects. He returned to recording in 1992 with Good as I Been to You, an acoustic collection of traditional folk songs. It was followed in 1993 by another folk record, World Gone Wrong, which won the Grammy for Best Traditional Folk Album. After the release of World Gone Wrong, Dylan released a greatest-hits album and a live record.

Dylan released Time Out of Mind, his first album of original material in seven years, in the fall of 1997. Time Out of Mind received his strongest reviews in years and unexpectedly debuted in the Top Ten, eventually climbing to platinum certification. Such success sparked a revival of interest in Dylan, who appeared on the cover of Newsweek and began selling out concerts once again. Early in 1998, Time Out of Mind received three Grammy Awards -- Album of the Year, Best Contemporary Folk Album, and Best Male Rock Vocal.

Another album of original material, Love and Theft, followed in 2001 and went gold. Soon after its release, Dylan announced that he was making his own film, to star Jeff Bridges, Penelope Cruz, John Goodman, Val Kilmer, and many more. The accompanying soundtrack, Masked and Anonymous, was released in July 2003. Dylan opted to self-produce his new studio album, Modern Times, which topped the Billboard charts and went platinum in both America and the U.K. It was Dylan's third consecutive album to receive praise from critics and support from consumers, and it was followed three years later in 2009 by Together Through Life, another self-produced effort (as Jack Frost) that also featured contributions from David Hidalgo of Los Lobos and Mike Campbell of Tom Petty & the Heartbreakers. He capped off the year with an old-fashioned holiday effort, Christmas in the Heart. Proceeds from the album were donated to various charities around the world.

Dylan released the self-produced (again as Jack Frost) Tempest on September 11, 2012; it debuted at three on both the Billboard 200 and the U.K. charts. The next two years brought acclaimed entries in the ongoing Bootleg Series -- 2013 saw the release of Another Self Portrait (1969-1971), which restored the reputation of a much-maligned era, and 2014 saw the long-awaited appearance of The Basement Tapes Complete -- and then Dylan threw a curve ball for his next studio album. Released in February 2015, Shadows in the Night found the singer/songwriter devoting himself to selections from the Great American Songbook in the pre-rock & roll era. Every one of the ten songs had previously been recorded by Frank Sinatra, and Dylan's album was his version of Sinatra's saloon songs, arranged by his own touring band. Shadows in the Night debuted at seven in the U.S. and at number one in the U.K. It was followed in the autumn by the next installment in The Bootleg Series, The Cutting Edge 1965-1966. Available in three editions -- a double-disc distillation, a comprehensive six-disc box, and a complete, limited-edition 18-CD set -- The Cutting Edge 1965-1966 collected unreleased (and unbootlegged) outtakes from the recording of Bringing It All Back Home, Highway 61 Revisited, and Blonde on Blonde.

In May 2016, Dylan returned with Fallen Angels, his second Sinatra-inspired collection of songs from the Great American Songbook; it debuted at number seven on the Billboard charts. Later that year, Columbia/Legacy released The 1966 Live Recordings, a 36-disc box set containing every known recording from that pivotal year, but its release was overshadowed by Dylan winning the Nobel Prize for Literature in the autumn of 2016. Dylan continued his exploration of the Great American Songbook with the March 2017 release of Triplicate, a triple album containing three thematically arranged collections of pop standards. Entitled Trouble No More 1979-1981, the 13th volume of The Bootleg Series spotlighted Dylan's Christian era in the early '80s and arrived in November 2017. Live 1962-1966: Rare Performances from the Copyright Collections, a double-disc set of highlights culled from previously released rarities collections, appeared in July 2018. Four months later, the six-disc deluxe version of More Blood, More Tracks: The Bootleg Series, Vol. 14 appeared. It contained all known studio recordings -- full and partial -- that eventually resulted in the classic Blood on the Tracks in 1975. Dylan further explored his 1975 archives in 2019, teaming with director Martin Scorsese for the documentary Rolling Thunder Revue: A Bob Dylan Story by Martin Scorsese. The film appeared in June, accompanied by a 14-disc box called The Rolling Thunder Revue: The 1975 Live Recordings. Later in 2019, The Bootleg Series, Vol. 15: Travelin' Thru -- a triple-disc set concentrating on Dylan's Nashville recordings of the late '60s, highlighted by his sessions with Johnny Cash -- was released.

Dylan released "Murder Most Foul," a nearly 17-minute track about the JFK assassination, on March 27, 2020. It was his first original song in eight years, and it was quickly followed by "I Contain Multitudes" and "False Prophet," a pair of singles that announced the arrival of his 39th studio album, Rough and Rowdy Ways, on June 19, 2020. Rough and Rowdy Ways debuted at number one on Billboard upon its release; it entered the U.K. charts at number one. The outtakes collection 1970 -- a set featuring unreleased material from the Self Portrait and New Morning sessions, including recordings with George Harrison -- appeared in February 2021. In September, Springtime in New York: The Bootleg Series, Vol. 16 (1980-1985) was released. Easily one of the artist's most provocative periods, it focused on the years that birthed Shot of Love, Infidels, and Empire Burlesque, with numerous unreleased outtakes, alternate takes, rehearsal recordings, and live performances.

—Stephen Thomas Erlewine

After spending much of the '90s touring and simply not writing songs, Bob Dylan returned in 1997 with Time Out of Mind, his first collection of new material in seven years. Where Under the Red Sky, his last collection of original compositions, had a casual, tossed-off feel, Time Out of Mind is carefully considered, from the densely detailed songs to the dark, atmospheric production. Sonically, the album is reminiscent of Oh Mercy, the last album Dylan recorded with producer Daniel Lanois, but Time Out of Mind has a grittier foundation -- by and large, the songs are bitter and resigned, and Dylan gives them appropriately anguished performances. Lanois bathes them in hazy, ominous sounds, which may suit the spirit of the lyrics, but are often in opposition to Dylan's performances. Consequently, the album loses a little of its emotional impact, yet the songs themselves are uniformly powerful, adding up to Dylan's best overall collection in years. It's a better, more affecting record than Oh Mercy, not only because the songs have a stronger emotional pull, but because Lanois hasn't sanded away all the grit. As a result, the songs retain their power, leaving Time Out of Mind as one of the rare latter-day Dylan albums that meets his high standards.

— Stephen Thomas Erlewine

Not long after attending the California funeral of his friend Jerry Garcia, Bob Dylan found himself snowbound at his Minnesota farm. He would listen to the storms and write after the sun sank from the winter sky. Those songs turned the cold environment into a crystalline lens on the tiring world—a place that was "not dark yet, but getting there," where "the blues [were] wrapped around my head."

What Dylan had left to say or whether he had any enthusiasm left for saying it had, for a while, been unclear. Seven years had passed since he had released an original new tune, and that album, Under the Red Sky, was a near-catastrophe, scuttling what had seemed a comeback after Dylan crept through his polarizing '80s evangelism. He had grown disillusioned with the cycle of writing and recording, he later said, and simply wanted to play.

During the '90s, he issued two solo acoustic albums of earnest, sometimes poignant renditions of American standards, delighting those who had pined for the lost days of the folk kid from Greenwich Village. But coffeehouse covers hadn't made Dylan a spark of resistance in the '60s or a source of bittersweet reckonings with reality in the '70s. He had become a legacy act, accruing lifetime achievement laurels and touring his hits for Boomers in khakis. Possibly for the first time in his career, Dylan was beginning to blend into the scenery.

But months after Garcia's funeral, Dylan approached the audacious producer Daniel Lanois. Since helming the contentious sessions for what many had prematurely considered Dylan's actual comeback, 1989's half-stepping Oh Mercy, Lanois had cut U2's Achtung Baby and Emmylou Harris' Wrecking Ball, a wondrously atmospheric abstraction of the singer's gorgeous and aging country vision. In a New York hotel room, Dylan read Lanois the lyrics and asked him if he had a record. "I said, 'Yes, Bob, I think we've got a record,"' Lanois remembered with a sly laugh during a recent phone call.

Dylan sent Lanois home with a list of reference records to study—Charley Patton, Little Walter, Little Willie John, a mix of ragged blues and primordial rock. "I listened to these records, and I understood," Lanois wrote in his memoir, Soul Mining. "A new birth with the old dogs under your arm, like a stack of classic books." In the end, that rebirth was Time Out of Mind, Dylan's 30th album and one that doesn't sound much like the basic blues at all. Instead, it is an essential post-modern reappraisal of them, an experimental consideration of what could become of the blues' sound and spirit and a mutual communion of articulate, exquisite despair. At the last minute, Lanois took Dylan's blurry snapshot for the cover of Time Out of Mind; on tape, that's exactly how he had captured him.

The next year was a reminder of what Dylan said he despised about making records—extended seaside sessions on the Atlantic and the Pacific, guitars smashed in anger, a militia of Nashville crackerjacks and world-class session players who had to be told more than once to play a lot less. Lanois and Dylan fought like hell in the parking lot of the Miami studio where they recorded, but after more than half a year and many mixes, overdubs, and lyrical revisions, Time Out of Mind—11 songs that would transform Dylan from seemingly obsolete icon to wise, wizened visionary almost overnight—was finished. And then Dylan nearly died.

Four months before Time Out of Mind arrived and just days after his 56th birthday, Dylan was admitted into a Los Angeles hospital after persistent chest pains that suggested a heart attack. Instead, acute pulmonary histoplasmosis—a nasty fungal infection caused by bird-and-bat feces in the country's most fertile river valleys—had inflamed the covering around his heart and nearly killed him. "I really thought I'd be seeing Elvis soon," he said later. For weeks between his hospital release and the album's release, Dylan was bedridden, emerging just in time to play for the pope in Rome and sit for a series of high-profile interviews that inquired not only about his near-death experience but also that of his career.

Dylan's brush with Elvis made for an easy press hook, especially given the twilit misery of Time Out of Mind. In its four-star review, Rolling Stone noted the album "confront[-ed] his advancing years and the prospects of failing health." In a moment of too-soon chicanery, Newsweek's cover joked "Dylan Lives."

But Time Out of Mind is not merely about death, though its inevitability looms at the periphery of these songs with the certainty of the setting sun; sometimes, death even seems for Dylan like the easy, desirous exit. Instead, Time Out of Mind is about dealing with life and its itinerant lows, knowing how it will all end, anyway. The blues become an emotional state of being. Through the cobwebs of his beleaguered voice, Dylan musters all the feelings of losing love, full of pride and insanity and lust and violence and humor, implicitly navigating the five stages of grief.

He writes with the hardened edge of Hemingway, trying to cloak feelings with callouses and sweetening his bitterness with a dash of wit. A portrait of the sometimes-awful truth about life and love, Time Out of Mind stands alongside Mark Rothko's so-called Black Paintings, conceived in poor health just before he killed himself, for its ability to stand at the lip of an abyss and stare into it. If you look long enough at the Rothko or listen closely to the Dylan, the most unexpected shapes will eventually stumble out of the dark.

Dylan begins in a bout of denial. At the start of "Love Sick," he shuffles through empty streets in the rain, a tangle of warped guitar, haunted organs, and faint drums aptly framing his bleak mood. He is mad at the world, judging its smiling people and castigating its illusion of happiness. "I'm sick of love/I wish I'd never met you," he calmly seethes in the closing chorus, addressing his ire not at anyone in particular but at the idea of human connection at large. "I'm sick of love/I'm trying to forget you."

But the first five minutes of "Love Sick," which sound so preternaturally cool and ultimately unaffected that the song was immortalized in a Victoria's Secret advertisement, are purely a pose. After Dylan sashays through that last refrain, he collapses into the confession that sets the tone for most of Time Out of Mind: "Just don't know what to do/I'd give anything to be with you," he sings, his voice now curdled. The band pulls back from the pulse and lets the melody dangle against the open air, as if they too are surprised by the sudden candor of their maestro. This is the moment where we get to the heart of Time Out of Mind, where Dylan crawls inside his own depression.

For most of the next 70 minutes, that's where he stays: Dylan's misery is so exhaustive that, during "Dirt Road Blues," he turns the sight of a rainbow into an instance of pain. Elsewhere, parties give him headaches. He is alternately cold and broke, hot and aimless. "It's such a sad thing to see beauty decay," he half-howls during "Cold Irons Bound," an aired litany of grievances that finds him losing most everything he holds sacred. "It's sadder still to feel your heart turn away."

Dylan hits rock-bottom during a duo of creeping existential crises, mercifully separated here by a swaggering barroom prowl. During "Not Dark Yet," he tells us he has been to "London… and 'gay Paree,"' reminders that he is a worldly sort who has had success and lived well. But here he is, shattered by the most pedestrian of things—love, or the loss of it—and tragically concluding "There's not even room enough to be anywhere." A decade before, he was coming down from his great Christian awakening. Now, he doesn't "even hear the murmur of a prayer." How could he fall further?

Lanois' production has often been criticized for warping Dylan's voice too much, for burying it in a cloud of effects. In early Time Out of Mind demos and outtakes, after all, Dylan practically sounds like Etta James, riding on top of his blues; on the record itself, he is pushing the words upward as an act of mere survival, letting them out so he can breathe back in. But the pervading murk of "Not Dark Yet" is exactly what these lyrics demand. As with the transmuted blues of Loren Connors or Grouper, Lanois lets Dylan flicker at the threshold of existence here, giving his troubles a sense of mortal urgency.

"Trying to Get to Heaven" is about being uncomfortable with everything and everyone everywhere—kicked out of Missouri, given false consolation in New Orleans, taken for a ride to nowhere in Baltimore. In the end, he simply falls asleep to escape inside his dreams, a world that now seems as concrete and meaningful as the actual people around him.

Strange as it may sound, "Trying to Get to Heaven" has long felt inspirational, given the subsequent arc of Dylan's career. "When you think that you've lost everything/You find out you can always lose a little more," he half-grunts toward the end, reaching the apogee of his sadness. But Time Out of Mind won three Grammys and kick-started Dylan's true second coming—a string of self-produced, hyper-stylized albums that turned his love of the blues, standards, and literature into impressionistic, intricate Americana and helped him on his way to a Pulitzer. In your grimmest moments, just remember how near-death Dylan sounds here—and exactly how much life he actually had left.

Even deep in his own hurt, Dylan maintains a sense of pride, hoping to preserve some dignity as he approaches his end. Amid the sad, stately waltz of "Standing in the Doorway," he tells his best lie: "I would be crazy if I took you back," he sings, the slide guitars curling beneath him like confused question marks. "It would go up against every rule." This is what he is supposed to say, of course, to save face when the entire album is about how not getting her back will be his ruin. Who hasn't been here before—completely despondent, but trying to pretend you've got the upper hand in some romantic standoff?

This is the softer, more playful side of Dylan's anger, but it occasionally flashes into hints of violence. When he croons "Don't know if I saw you, if I'd kiss you or kill you" early in the album, it feels like a lonely abstraction, a what-if penned from a distance. By record's end, though, it has morphed into real menace. Breathing fast, pulse racing, he's doing his best to hold himself together during "Can't Wait," trying not to lash out or do something he will live to regret. The guitars slash, and the organs roar, fighting the same urge to explode. "If I ever saw you comin', I don't know what I might do," he yells as best he can. "I'd like to think I could control myself, but it isn't true." His sadness, at last, has beaten his civility.

In spite of its presiding gloom, Time Out of Mind actually delivered a new Dylan standard—his first hit in decades and a song that has become almost as ubiquitous as "Like a Rolling Stone" or "Forever Young," even if he mostly hasn't been the one to sing it. A month before Time Out of Mind arrived, Billy Joel turned the spare ballad "Make You Feel My Love" into a bombastic, string-swept single, shouting the lyrics and howling behind the harmonica like it was he who stepped onstage at Newport in 1965. Twin versions by Garth Brooks and Trisha Yearwood soundtracked the 1998 rom-com Hope Floats, while takes from Neil Diamond, Ed Sheeran, and Kelly Clarkson have followed. But it was Adele's piano-and-cello lament—and its subsequent appearance on "Britain's Got Talent"—that turned Dylan's ostensible love song into an international standard and, according to Adele, made Dylan at least a million pounds in a year.

But what is there on Time Out of Mind to suggest that Dylan had suddenly turned soft for three minutes, that he would dip so smoothly into guileless piano ballads? Absolutely nothing. In the preceding song, he's so tormented his crops are dying and all his friends are traitors; in the next song, he wonders again if he could control his violent impulses if he encountered his paramour. This isn't the sort of person who shuffles over to the piano and readily forgives. This is the sort of person your friends warn you about, the guy who shows up drunk at 3 a.m. and slurs drunken promises as he bullies the doorbell.

All the song's romantic images about warm embraces and dried tears and self-sacrifice are purely hypothetical, things he "could" do if the subject would simply submit to his advances already. In the five stages of grief, this is bargaining, and it's a particularly nasty business here. "I know you haven't made your mind up yet, but I would never do you wrong," he pleads, the trace of guilt in his voice vanishing as quickly as it appeared. He makes his demand clear. "I've known it from the moment that we met/No doubt in my mind where you belong." In context, "Make You Feel My Love" is not a romantic bauble; it is an ironclad threat in a velvet glove, one final attempt to force love from the listener at any cost.

The Dylan faithful largely hated "Make You Feel My Love" from the start. Ian Bell—the late British journalist and exhaustive Dylan analyst—quipped that the song "should have been shipped off instantly, gratis, to Billy Joel, Garth Brooks, and the rest of the balladeers who would take the vapid things to their sentimental hearts." It is a song worth reconsidering, though, not in Joel's mawkish translation or even Adele's austere one but instead in its original setting. Those famous covers alternately sound triumphant or plaintive, suitable enough for a standalone single.

But even as Dylan plays tender piano above a pillow-top organ, he sounds absolutely broken, the cracks of his voice widening into chasms. There's occasionally a whisper of percussion and a distant acoustic guitar lick, but he's mostly left to wrestle these feelings himself. This is the real pit of his desperation, concealed to read like romance in order to save face. It is an essential piece of this picture, a last-ditch attempt for sanity from someone who has lost control.

In the end, Dylan pulls himself together, at least enough to survive for a while longer. Time Out of Mind ends with "Highlands," a brilliant and occasionally hilarious 17-minute shuffle that frames life's endless numbered days as a string of largely meaningless moments. "Feel like I'm driftin', driftin' from scene to scene," Dylan mumbles in a monotone fit for someone who has simply resigned himself to exist. "I'm wonderin' what in the devil could it all possibly mean." He listens to Neil Young, avoids a sad dog, ponders his wardrobe, envies young people, and details an awkward encounter with a waitress in a Boston café that paints him as an artist perennially uncomfortable with his audience. All the while, he daydreams of the Scottish Highlands and its verdant scenery—for him, heaven, or "where I'll be when I get called home." He understands his age and fate, even if he longs for youth. Without the ballast of his love, this moribund acceptance becomes his life.

The total craft of Time Out of Mind, the dry spell that preceded it, and the saga that produced it collectively serve a cautionary function. If you hadn't given up on Dylan by 1997, you were either a zealot who would eke merit from most anything he made or a casual fan who had stopped paying enough attention to have a strong opinion. But the sophistication and nuance of Time Out of Mind work only because Dylan had become a wunderkind, gone electric, faced backlash, crashed his motorcycle, wrecked his marriages, found his faith, faltered in it, fathered a family, seen his kid become a rock star, lost old friends, wavered in relevance, and wondered if he cared about any of it anymore at all. The extra grain in his voice, the lessons of his words, the disorienting blur of his band: It is the sublimated sound of actual pain, lived and analyzed and announced in songs that show you exactly how dark the world can get.

Time Out of Mind feels like the antithesis of our pervasive need to have an opinion about everything all the time. It is a reflection on a life lived, not a reaction to someone else's ideas. There's a place for both, as Dylan's own brash, youthful songs made clear a half-century ago. The difference is one of insight, of 55 years of life slowly distilled into wisdom. Everything won't be alright, but desolation can be its own unlikely source of triumph. Dylan had a grief that gave him nowhere to go but the grave—or, as he did, onward.

— Grayson Haver Currin