A guide to Bob Dylan, from the ’60s to now 

A guide to Bob Dylan, from the ’60s to now 

Primer is The A.V. Club’s ongoing series of beginners’ guides to pop culture’s most notable subjects: filmmakers, music styles, literary genres, and whatever else interests us—and hopefully you. This installment: the work of singer-songwriter Bob Dylan.

Bob Dylan 101
After creating a new name and a fanciful origin for himself, Minnesota-born Robert Allen Zimmerman had already started to make waves in the New York folk scene by the time his second album, The Freewheelin’ Bob Dylan, hit stores in 1963. But Freewheelin’ cemented him as the central figure of folk music in the early ’60s, positing him in the public imagination as a righteous, imaginative singer and songwriter equally concerned with the news of the day and with matters of the heart. Dylan quickly found that identity burdensome, but here, he wears it well, alternating inspiring (“Blowin’ In The Wind”) and fearsome (“A Hard Rain’s A-Gonna Fall,” “Masters Of War”) protest songs with wistful love songs like “Don’t Think Twice, It’s All Right.” Both the politics and the wistfulness owe much to Dylan’s on-and-off relationship with Suze Rotolo. Rotolo, the daughter of American communists who didn’t approve of her relationship with Dylan, shares the famous cover with him, providing a peaceful image for a collection otherwise characterized by passion.

Dylan’s subsequent albums deepened his reputation as a topical songwriter and as an artist capable of imbuing love songs with his own personal perspective. Had he somehow stopped making records after 1964, his status as an icon of the period would already be secure. But his greatest work lay ahead, and would explode in a burst of activity over the next three years. Dylan went from folk to rock on 1965’s Bringing It All Back Home—or, rather, went from folk to folk and rock. Split between “electric” and “unplugged” sides, Home can be described as a transitional record, easing fans from the guitar-and-voice Dylan of the early ’60s to his new “thin wild mercury” sound. But any album that begins with the proto-rap of “Subterranean Homesick Blues” and ends with the visionary “It’s All Over Now, Baby Blue” shouldn’t be described solely in terms of how it relates to what came before and after. Home is a major statement in its own right, though the much-ballyhooed, controversial rock songs (which include classics like “Maggie’s Farm” and “Love Minus Zero/No Limit”) end up taking a backseat to the breathtakingly ambitious and stunningly beautiful compositions on side two. Ostensibly keeping with Dylan’s “old” sound, tracks like “Mr. Tambourine Man” and “It’s Alright Ma (I’m Only Bleeding)” are acoustic, but they’re hardly traditionalist folk. Infusing some of his best-ever melodies with surreal language loaded with indelible images and incomprehensible wordplay, Dylan finally outgrew the scene that birthed him, and he carved out a new space only he would occupy for the next few years. 

Dylan’s forays into rock music on Bringing It All Back Home sound tentative by comparison to the confident, full-bodied eruption that is “Like A Rolling Stone,” the revolutionary opening track of 1965’s Highway 61 Revisited. Dylan likened writing “Stone” to vomiting, and while he cut the song down considerably from the 10-page screed that originally poured out of him, it was still a declaration of independence from his musical past, and from anything and everything happening around him at the time. The lyrical breakthroughs from the second side of Home were now being applied to approximations of Chicago blues. Backed by a bountiful mix of slashing guitar, barrelhouse piano, and otherworldly organ fills, Dylan created a sound that formed the core of roots rock music for decades to come. Adding his funny, spiteful, mind-bending lyrics to the mix redefined what rock music could be. It isn’t that Highway 61 was more “profound” than rock records before it; the album merely showed that musicians could do anything they wanted in a rock context. Highway 61 drew on Rimbaud, James Dean, Howlin’ Wolf, Allen Ginsberg, the Bible, Federico Fellini, and Little Richard, reshaping these diverse influences to fit the sensibility of a gangly, weirdo Midwesterner who wanted to be bigger than Elvis. 

So many superlatives have been heaped on “Stone” and Highway 61 that it can be a challenge for neophytes to unpack all the baggage and appreciate them as music. Every song on Highway 61 has been analyzed, deconstructed, and recontextualized. But once that thunder-crack snare from “Stone” kicks the album off, all that conversation falls away. Even after taking it out of the context of its time period, this is still sublime rock ’n’ roll, played with careless ambition and reckless abandon by a young genius making it up as he goes along. 

Highway 61’s even more ambitious sequel, Blonde On Blonde, opens with the boisterous sing-along and future classic-rock-radio staple “Rainy Day Women #12 & 35,” a goofy lark that doesn’t really suggest the masterpiece that follows. Working largely in Nashville with a lineup that included members of The Hawks—a mostly Canadian rock ’n’ roll band Dylan hired to be his backing band on tour—and Nashville session musicians, Dylan takes his amphetamine-stoked fusion of folk, blues, and rock music as far as it can go, singing and playing harmonica with an almost-scary passion over his collaborators’ grooves, and reeling off a cryptic, evocative string of words that’s alternately wry, restless, and heartbroken. It all spills out into the side-filling, 14-minute final track, “Sad-Eyed Lady Of The Lowlands,” which sounds like the work of a man making peace with the drama and disappointment that preceded it.

If Dylan is no longer the most bootlegged artist ever—the Grateful Dead, Phish, and dozens of other lesser jam bands might have surpassed him by now—then he’s certainly the first most bootlegged artist in rock history. Along with the treasure trove of Basement Tapes that were widely circulated (often under the name Great White Wonder) among Dylan fans until the official release in 1975, there was the “Royal Albert Hall” concert recording from 1966. Actually recorded at Free Trade Hall in Manchester near the end of Dylan’s first “electric” tour, and finally released as a sanctioned album in 1998 as The Bootleg Series Vol. 4: Bob Dylan Live 1966, The “Royal Albert Hall” Concert, it captures him at his most iconic, playing beautiful, stoned-sounding psychedelic folk songs on one disc, and fronting The Hawks for the angriest, most mind-blowing rock music of his career on the other. The electric disc includes the famous “Judas!” moment, an insult hurled at Dylan by an anonymous fan right before the night’s set-closer, “Like A Rolling Stone.” It’s mind-boggling that anyone privileged enough to witness a night of such overwhelming (and historically important) music could still have such a petulant attitude. But it adds to the drama of the album, not to mention Dylan’s furious energy: His climactic demand to “play fuckin’ loud” before leading The Hawks into a hell-raising “Stone” is one of the great moments in rock. 

Dylan disappeared not long after the so-called “Royal Albert Hall” concert, the victim of a motorcycle accident whose severity and circumstances remain an item of debate. Retiring, temporarily, from public life, he holed up in his Woodstock home, and in 1967, he began recording again with The Hawks, who were then in the process of becoming The Band. Much of the recording took place in the basement of his collaborators’ home, Big Pink. Later dubbed The Basement Tapes, these loose, informal sessions mixed new Dylan tracks, covers, and goofery, in the process stumbling on a volatile fusion of rock and traditional American music. Columbia circulated some of the sessions as demos for other artists, and covers started to emerge as a result: “Too Much Of Nothing,” “Nothing Was Delivered,” “Quinn The Eskimo,” “Tears Of Rage,” and “You Ain’t Goin’ Nowhere” all originated in the basement sessions. 

The tapes themselves were never meant to see the light of day, but a few were released on the Great White Wonder bootleg, which hit stores, unofficially, in 1969, revealing not just the songs, but the spare, loose sound that proved so influential as more musicians began incorporating traditional influences in the late ’60s and early ’70s. More songs saw official release as part of the 1975 album The Basement Tapes, which overdubbed some recordings and added stray songs by The Band, but otherwise offered many of the high points of those fruitful hours. But to fully appreciate The Basement Tapes, listeners should dive into the deep end and spend time with the full sessions that surfaced on the bootleg market in the ’90s as a five-disc set. They aren’t hard to find on the Internet. While an official release is probably inevitable at some point, their shadowy semi-official state is fitting. Murky, mysterious tracks filled with false starts, dead ends, and more than a few moments of transcendence, they remain rock’s great mystery recordings.

Dylan’s trilogy of mid-’60s rock albums inspired legions of artists who proceeded to “invent” the ’60s as a concept in the second half of the decade. As for Dylan himself, he retreated into family life and back to the bedrock American music and tall tales that originally entranced him as a young man. After recording so many songs during the Basement Tapes sessions, he took a different batch of new tunes down to Nashville and recorded 1967’s John Wesley Harding in just 12 hours. By contrast with his recent rock records and live shows, Harding has spare musical backing, with Dylan strumming acoustic guitar and blowing harmonica over the remarkable rhythm section of bassist Charlie McCoy and drummer Kenny Buttrey. Dylan’s lyrics were similarly stripped-down and direct; Biblical imagery had long been a part of his songs, but they became especially prominent on Harding, with Dylan’s writing aspiring to the simplicity of parables and gospel stories. Unlike the beatific, hippiefied folk-pop just starting to come into vogue at the time, Harding is not a feel-good record. It’s an album full of apocalyptic warnings and dark truths, a lightning-streaked storm crawling over the horizon with a slow, foreboding inevitability. 

By the mid-’70s, Dylan was perceived by many to be past his prime as a songwriter. A record-setting tour with The Band in 1974 testified to his continued popularity, but it had been several years since he had put out an album that lived up to his “classic” output. Finally, with 1975’s Blood On The Tracks, Dylan returned to form, and in some respects, even surpassed it. The introspective singer-songwriters of the ’70s had taken Dylan’s influence in a laid-back, pop-friendly direction, but with Tracks, Dylan topped Jackson Browne, James Taylor, and their contemporaries at their own game, singing about the sad side of love with brutal honesty and uncommon artistry. 

A song cycle about the end of a romantic relationship, Tracks was widely seen as a running commentary on the end of his own marriage, an interpretation the famously private Dylan denied. The degree to which songs like “You’re A Big Girl Now” and “If You See Her, Say Hello” are autobiographical isn’t really important; Dylan’s bruisingly frank depictions of the sorrow, anger, loneliness, and finally acceptance felt in the wake of a breakup are so relatable and true to life they operate as a sort of universal autobiography for the brokenhearted. As he did so often in his career, Dylan returned to his original, folk-based sound for Tracks, though his lyrics now had the benefit of a more grown-up perspective. 

Blood On The Tracks was an album Dylan could have made only in his mid-30s, after he had a little more life under his belt. 1997’s Time Out Of Mind, similarly, reflects the mood of a man entering the later stages of his life and coming to terms with mortality. Released after a long, creatively fallow period, Mind was widely hailed (like countless other, lesser Dylan albums) as his best since Blood On The Tracks. In Mind’s case, this was actually true, and the album set a new benchmark for subsequent Dylan records. On his debut album, Dylan sang several songs about death; Mind is just as obsessed with the end of life, only now, Dylan addresses the subject with far more eloquence and urgency. (He contracted a near-fatal lung disease shortly after the album was completed.) The album’s spooky vibe owes a lot to Daniel Lanois’ distinctive production (which Dylan later criticized), but Dylan’s songs and his haunted vocal performances push Mind into the essential part of his discography.  

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Intermediate work
In many respects a sequel to Freewheelin’, 1963’s The Times Are A-Changin’ tilts the balance toward protest songs, opening with the opaque but insistent title track and bringing assured fury with tracks like “With God On Our Side,” “Only A Pawn In Their Game,” and “The Lonesome Death Of Hattie Carroll,” the lattermost inspired by the murder of a black woman by a white man in 1963. Dylan later eschewed “finger-pointing songs,” but his third album offered some of the finest examples of the genre.

That move away from topical songs began with the following year’s appropriately named Another Side Of Bob Dylan. Recorded in a single session, Another Side shifts the focus again, offering confessions and personal reflections in place of topical songs. In some ways, he had no choice but to make that shift, having publicly broken with the folk and protest movements while drunkenly accepting the Emergency Civil Liberties Committee’s Tom Paine Award in December 1963. Politics still surfaced in tracks like “Chimes Of Freedom,” but three-dimensional, not-always-flattering depictions of romantic love like “All I Really Want To Do” and “It Ain’t Me Babe” dominate the album. Most telling of all, the song “My Back Pages” sounds like a farewell to his protest instincts, with its reference to “lies that life is black and white” and a refrain that echoed his Tom Paine speech, suggesting his head was elsewhere: “I was so much older then / I’m younger than that now.” In November of 1964, Irwin Silber, editor of the folk magazine Sing Out!, penned an open letter to Dylan calling his new material “inner-directed now, innerprobing, self-conscious—maybe even a little maudlin or a little cruel on occasion” and noting “you seem to be in a different kind of bag now, Bob.” He couldn’t have known how different that bag was about to get.

Where John Wesley Harding confounded expectations, Nashville Skyline slipped away from them entirely. The solidly mainstream country album found Dylan slipping into the role of a countrypolitan crooner. On some tracks, one of the most distinctive singers around barely sounded like himself, as he was playing the part of a country singer. He slipped into the role well, however, and in spite of mixed reviews and an unsure reception at the time, time has been kind to the album. Particular standout tracks are “I Threw It All Away” and the hit “Lay Lady Lay.”

A companion piece to Blood On The Tracks recorded between stretches of the Rolling Thunder Revue tour inspired by that album, Desire is shorter and less consistent than that masterpiece, but compelling in spite of some glaring flaws—at times even because of those flaws. “Joey”—like most of the album’s songs, co-written by songwriter-theater director-psychologist Jacques Levy—pays tribute to gangster Joey Gallo, but somehow works in spite of some dubious fact-fudging, even more dubious rhymes, and a seemingly endless running time. Much less questionable: “Hurricane,” an epic return to protest songs about the incarceration of Rubin “Hurricane” Carter. Plus some of the most personal-sounding songs of Dylan’s career: “Isis,” “One More Cup Of Coffee,” and “Oh, Sister.” Then there’s “Sara,” a heartfelt tribute to Dylan’s wife filled with autobiographical details and elegiac underpinnings. Within a year, they’d be in the midst of an ugly divorce.

The ’80s were a tough, confused, frequently flat-out terrible period for Dylan. Every other decade boasts a surplus of good-to-brilliant work and some failures, but most of Dylan’s ’80s output was regrettable. Much of this is due to Dylan’s indifference to the craft of making records, which had become epidemic by this time. Even really good songs from this period were all but thrown away due to poor production. This was finally rectified on 1989’s Oh Mercy, when Dylan employed his eventual Time Out Of Mind collaborator, Daniel Lanois, who coated the songs in a swampy reverb fog that brought some of the mystery back to Dylan’s music. More importantly, he pushed Dylan to play his own parts rather than fly in session musicians. Not everyone was happy about the sound of Oh Mercy or Lanois’ heavy-handed style: It ranks with Mind as the most “produced” album in Dylan’s catalog, a stylistic anomaly in a sea of freewheeling, underplanned records. But Oh Mercy also boasts Dylan’s strongest set of songs since the ’70s—he wrote extensively about the intense rush of inspiration he experienced at the time in his memoir, Chronicles, Vol. 1which makes it a shoo-in for his best album of the ’80s. 

Time Out Of Mind heralded Dylan’s official comeback in the late ’90s. This is definitely true of Dylan the songwriter, but all the comeback talk surrounding Time overlooked two very good records earlier in the decade where Dylan rediscovered his prowess as an interpreter of ancient folk and blues songs. 1992’s Good As I Been To You and 1993’s World Gone Wrong were the first albums in nearly 30 years where Dylan was accompanied only by his guitar and occasional harmonica. They’re also his only records that contain no original compositions, which explains why they’re often overlooked among people discussing Dylan’s work from this time. But both albums, especially World Gone Wrong, are absolutely essential to understanding Dylan’s artistic rebirth later in the decade and beyond. Dylan’s early-’90s folk records were like a reset button for his career, bringing him back to where he started in the early ’60s, so he could rebuild his music and take it in a new direction after bottoming out in the ’80s. 

How do you follow up an album about finality? For his follow-up to Time Out Of Mind, Dylan opted to look backward. Released in 2001, Love And Theft finds Dylan settling into the role he’s played on records ever since: a preserver of tradition. Drawing on traditional blues and country—and digging back into the pre-recorded musical past—Dylan sounds relaxed and ruminative, delivering songs that sound as if the turnings of the 20th and 21st centuries have been folded together. The victims of “High Water (For Charley Patton)” could come from any time in history when the winds of change hit the disadvantaged harder than those in power. Like the albums that follow, it’s the work of a man comfortable with his own place in musical history, but still striving to contribute to it.

Advanced studies
Bob Dylan’s self-titled 1962 debut sounds slightly unformed and raw compared with what came immediately after. But factoring in his age at the time (he was a baby-faced 20-year-old) and relative lack of experience (he was barely two years out of Hibbing High School), Bob Dylan is a remarkably prescient album, pointing the way to where Dylan was headed in the years ahead. It was recorded quickly and cheaply, and proved to be a learning experience for Dylan, who initially struggled to sing properly into the studio mic. Most of the songs were standards from the New York folk scene, and many of them were about death. Dylan tries to affect a gravity in his voice that he wouldn’t achieve legitimately for another 40 years, but he’s at his best when he sounds his age on one of the album’s only originals, “Song To Woody,” a moving tribute to his mentor, Woody Guthrie. 

In 1973, Dylan moved to California, where David Geffen wooed him away from Columbia for an album and a tour with The Band, which had become a success in its own right in the intervening years. The reunion resulted in Planet Waves, a well-received but slow-selling album, followed by a successful tour. While the tour found some of the old chemistry between Dylan and The Band, it’s only intermittently evident on Planet Waves, a solid effort highlighted by “On A Night Like This” and “Forever Young,” the latter in two different versions.

Recorded between his booze and drug-fueled Rolling Thunder tours and his eventual conversion to Christianity, 1978’s Street-Legal came out of a deeply unhappy time in Dylan’s life. His marriage had finally fallen apart, and he was approaching 40 with a deep sense of personal dissatisfaction. All of this is apparent in the music, which is equal parts bitter, strange, and epic. Street-Legal’s punchy commercial sound is a concession to late-’70s album-oriented rock radio, and the overbearing presence of female backing vocalists suggests that Dylan was attempting, in his own idiosyncratic way, to court pop-music listeners. The songs themselves are the opposite of pop: “Changing Of The Guards” is a thick tangle of lyrical metaphors that’s hard to decipher even after dozens of listens, “New Pony” is perhaps Dylan’s dirtiest sex song, and “No Time To Think” is a bizarre waltz that piles on verse after verse for more than eight minutes. The pain in Street-Legal can be off-putting; even the pretty “Is Your Love In Vain?” comes with a dose of anger that curdles into misogyny. But there’s some essential music here, especially the great story song “Señor (Tales Of Yankee Power),” which unfolds as dramatically as a Sergio Leone shootout. 

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In November 1978, a fan threw a cross onstage in San Diego and changed Dylan’s life. The cross-throwing incident opened one of the strangest chapters in Dylan’s career. In his hotel room the following night, Dylan picked up the cross and had what he described as a conversion experience. He started working Christian-themed material into his shows. In January 1979, he formalized his commitment, meeting with members of California’s Vineyard Christian Fellowship, an evangelical church that emphasized end-times prophecies. That year he also committed his new faith to record with Slow Train Coming, the first, and best by a good margin, of three explicitly Christian recordings. Highlighted by guitar contributions from Dire Straits’ Mark Knopfler and contributions from a gospel backing group, Slow Train Coming finds Dylan training his expressive powers toward evangelical ends, turning himself into an assured preacher with a clear-eyed, black-and-white sense of right and wrong, reminiscent of his protest days. (It’s fitting that Todd Haynes connected the two periods in his inventive Dylan-themed film I’m Not There.) It’s an unexpected detour, narrow in its focus and often narrow in its view of the world. But it’s also stirring, and too moving even for the faithless to dismiss.  

Coming after the doldrums of Dylan’s born-again period, 1983’s Infidels was heralded by some at the time as a return to form. It’s not, but after Oh Mercy, it’s Dylan’s best album of the ’80s. Working with an all-star cast of musicians, including Knopfler, Mick Taylor of The Rolling Stones, and the reggae group Sly & Robbie, Dylan has musical chops on Infidels that can’t be denied, even as the ’80s production takes away much of his band’s grit. Like Street-Legal, Infidels was Dylan attempting to make a contemporary-sounding rock record, and the ballad “License To Kill” and the hard-charging political song “Neighborhood Bully” aren’t far removed from the sound of Tom Petty records from the early ’80s. And yet even Infidels is frustrating for what it could have been: For whatever perverse reason, Dylan opted not to include his greatest song of the ’80s, the hymn-like “Blind Willie McTell,” on the album. (The song later was released as part of The Bootleg Series: Vol. 1-3.

Speaking of The Bootleg Series Volumes 1-3 (Rare & Unreleased) 1961–1991, the first disc is as essential as any official album, offering a shadow history of Dylan’s recording career that includes everything from early oddities like a waltz-time take on “Like A Rolling Stone” to discards any other artist would be happy to claim. If nothing else, the set confirms that Dylan hasn’t always been the best judge of his own material. Vol. 7: No Direction Home, the soundtrack to Martin Scorsese’s documentary of the same name, scares up more worthy oddities, while Vol. 8 — Tell Tale Signs: Rare And Unreleased 1989–2006 continues the story with worthwhile almost-rans from the later years that rival the better-known songs on the albums from that period. The series’ most recent installment, Vol. 9 — The Wittmark Demos: 1962–1964, collects intimate versions of early Dylan songs recorded as demos for artists who might be interested in covering them. It’s a fascinating listen, both for its spareness and for the way it captures Dylan as a guy hoping to sell a few songs to interested parties.

Released in 2006 and 2009, respectively, Modern Times and Together Through Life are both in the vein of Love And Theft: solid, easy-to-recommend efforts from an elder statesman who never lost the habit of writing songs and has kept his craft sharp as the years have gone by. Neither feels like a major statement, nor do they feel like an artist content to coast, or lost and in search of inspiration. (Dylan seems to have put that period behind him in the ’80s.) 

Demerits
No one can accuse Bob Dylan of being overly reverent about his own past. Dylan has the opposite problem: He can be his own worst interpreter. That’s the case with 1979’s misbegotten Bob Dylan At Budokan, a disastrously glitzy redux of Dylan’s greatest hits that sounds like a clueless cover band gracelessly clubbing all the beauty and nuance out of his best material. Dylan is notorious for reworking his most familiar songs in a live setting, and the results are frequently worthwhile, or at least interesting. But he shows alarmingly little feel for his own songs on At Budokan, wrecking the melodies, then blowing them out with a legion of horn sections and backup singers.

Dylan’s decision to make his Christianity the central theme of his music in the late ’70s can be read as brave and even daring. And when he was armed with good songs, like on Slow Train Coming, the subject matter hardly ever got in the way of appreciating the music. But on 1980’s Saved and 1981’s Shot Of Love, Dylan’s preachiness became too loud to ignore. Saved is the finger-pointiest of the born-again albums, and all but impossible for fans to enjoy if they don’t share Dylan’s religious beliefs. Shot Of Love is better, and even boasts his best “religious” song, “Every Grain Of Sand.” But a Dylan collection without “Property Of Jesus” probably won’t feel incomplete. 

Apart from Paul Simon, few veteran ’60s artists had a good time of it in the ’80s, when gated snares and watery synths became the dominant sound; it seemed like simply picking up a guitar and playing wasn’t an option anymore. Dylan had a worse decade than most, particularly toward the end of it. In 1985, Empire Burlesque kicked off a trilogy of weak-to-awful albums that found Dylan struggling to find inspiration and chasing trendy production techniques that played against his strengths. Knocked Out Loaded and Down In The Groove are worse still, but even the weakest Dylan albums usually have something to recommend them. Rescue the sprawling “Brownsville Girl” (co-written with Sam Shepard) and “Death Is Not The End” for your Dylan playlists, and leave the rest. (Dylan’s first album after his Oh Mercy comeback, 1991’s Under The Red Sky, plays more like a companion piece to these than a proper continuation of its predecessor.)

Miscellany 
Bob Dylan has released several live albums, the best being the previously mentioned Bob Dylan Live 1966. All of the Bootleg Series live records are worth hearing, especially The Bootleg Series Vol. 5: Bob Dylan Live 1975, which chronicles the mid-’70s Rolling Thunder tour. (It’s preferable to 1976’s Hard Rain from the same period, though that album has its merits.) Another worthy live record is Before The Flood, which was recorded during Dylan’s tour with The Band in 1974. Dylan’s ’80s live albums are more problematic: 1984’s Real Live is for completists only, and 1990’s Dylan & The Dead (taken from a brief 1987 tour) is a slog. 

Dylan has dabbled in film throughout his career, with mostly undistinguished results. His performance in Sam Peckinpah’s Pat Garrett And Billy The Kid is practically nonexistent, but his soundtrack has some nice instrumentals, and it spun off one of his best-known songs, “Knockin’ On Heaven’s Door.” Dylan tried his hand at directing with 1978’s Renaldo And Clara, a four-hour mishmash of live performance footage from the Rolling Thunder tour and improvised dramatic scenes starring musicians from Dylan’s band. The film received an extremely limited run, and since it was subsequently pulled from distribution, has been rarely seen since. Two other films starring Dylan, 1987’s Hearts Of Fire and 2003’s Masked And Anonymous, were also poorly received, though the latter has a great cast (including John Goodman, Val Kilmer, Luke Wilson, and Mickey Rourke) and a certain loopy charm, due to being structured like a long, meandering Dylan song. 

Most of Dylan’s cinematic adventures belong in the “optional” category. Not so for Don’t Look Back, a D.A. Pennebaker-directed account of Dylan’s 1965 tour of Great Britain. The film captures a man at the end of his rope, exhausted by reporters (whom he taunts), tired of the responsibilities of political activism (and Joan Baez, the girlfriend who embodies those responsibilities), and ready for something new. Martin Scorsese’s 2005 documentary No Direction Home is longer and much more conventional, but well worth the time. Scorsese focuses on Dylan’s early years up through the motorcycle accident. The narrative that emerges isn’t that far removed from that of Raging Bull or Goodfellas, all stories of men who got what they wanted and were undone by their success—if here only temporarily.

Tarantula, Dylan’s stream-of-consciousness novel written in the mid-’60s, but only officially released in 1971, is strictly for the dedicated. But Chronicles: Volume One, the first of a proposed, seemingly stalled series of memoirs, is essential. Jumping between his early years and the periods in which he recorded New Morning and Oh Mercy, it’s a clear-eyed, spirited look back. It also pulls off the weird trick of being frank and mysterious, sliding back the curtain just enough to suggest Dylan is still concealing a great deal.

The weirdest album in Dylan’s catalog has to be 2009’s Christmas In The Heart. A straightforward collection of holiday carols, Heart finally satisfies the demands of fans who longed to hear Dylan lend his old-man croak to “Winter Wonderland” and “Here Comes Santa Claus.” If the album is supposed to be a joke, Dylan manages to hold back his smirk. As it is, while Heart isn’t particularly listenable, it’s still a hard album to hate. Dylan’s decision to donate all of his royalties from the album add to the sense that Heart is an odd but good-natured folly.

Top 5 albums

1. Highway 61 Revisited
A landmark album that somehow sounds as fresh today as ever, Dylan’s declaration of independence from other people’s labels vibrates with nervous energy. The sound is in love with words and music, and he tries to bend both into the shapes in his mind through sheer force of will. 

2. Blood On The Tracks 
The great album of breaking up, growing disillusioned with the past, and moving on, Blood On The Tracks is the sound of ’60s folks trying to make sense of the less-hospitable ’70s, but it’s the perfect accompaniment to anyone figuring out that being a grown-up presents challenges much different from being young.

3. Blonde On Blonde 
It speaks to the quality of Dylan’s best albums that a record as titanic as Blonde On Blonde comes in at No. 3 on this list. It’s the peak of Dylan’s most creative period, and its mix of rock, blues, and psychedelia helped create the idea of the ’60s as we’ve come to know it. 

4. John Wesley Harding 
An album out of its time, John Wesley Harding found Dylan working with none of his Basement Tapes conspirators, but drawing on the haunted Americana he and The Band conjured up on those sessions. It’s a revisionist Western in album form, using traditional sounds to reinterpret our shared musical past and what it meant for the present.

5. Time Out Of Mind 
What Blood On The Tracks is to breaking up, Time Out Of Mind is to grappling with mortality. An album that fully restored Dylan’s artistic standing, Mind was an album only a fiftysomething Dylan could’ve made, reflecting a singular point of view at a specific time and place in his life as effectively as any of the records he made as a much younger man.

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