The Essential Bob Dylan

From the young folkie of the early 1960s to the gruff old crooner of the present day, Bob Dylan’s influence on modern music is beyond measure – and, as Gary Tipp discovers, his vinyl back catalogue ain’t bad either…

Over the course of a recording career stretching back to 1962, Bob Dylan’s songwriting genius, amazing vinyl output and singular approach to the music business has made him one of the most iconic and influential performers popular music has ever known. Let us back up that claim.

He played a major role in the evolution of the singer-songwriter by injecting self-reflection into folk songs. His cryptic, quick-witted lyrics went a long way to enlarge pop’s vocabulary and meant rock could be regarded as a serious Pulitzer-worthy artform. He hurried along the advent of 70s country-rock after recording in Nashville with veteran session musicians. And his by turns cocksure, droll, conceited, clever and mean persona created a template still emulated by swaggering rock stars to this day.
Dylan didn’t gain his fabled status by standing still and, over the course of the decades, he is famed not only for his changes in musical direction, but also the series of curveballs he has thrown out to his adoring fanbase. The early 60s began with him in the thrall of Woody Guthrie. His first three albums saw him adopted by the folk scene and proclaimed as ‘the voice of his generation’ for his protest songs.
It was an unwanted tag that prompted him away from rallying-cry anthems and towards a more introspective style, with dense lyrics full of abstract metaphors. The voice of his generation hadn’t exactly clammed up but, much to the vexation of the folk fraternity, his scope was merely personal.
Then, to add insult to his folk fans’ injury, he put aside his acoustic and plugged in his electric. His ‘rock’ albums thrilled the mainstream audience, but then the electricity was turned down a notch as Bob embraced
a country-tinged sound.
The 70s were understandably patchier, but still witnessed the peerless Blood On The Tracks and Desire. This is before his conversion to born-again Christianity confused the bejesus out of just about everybody. The 80s, on the other hand, were a washout – with Dylan out of step with just about everything. The 90s started off shakily, too, but eventually witnessed a renaissance (Time Out Of Mind) that continued through into the new millennium (Love And Theft).
Finally, his deep archive of demos, unreleased songs and live performances was raided through The Bootleg Series (it’s now up to Vol. 13) and their serious critical reappraisal underlined what we all knew in the first place: Dylan is one of the few true geniuses of popular music.


According to legend, the 20-year-old Dylan bashed out one of his most important songs in 10 minutes in between espressos in a New York coffee house. By putting lyrics to an old spiritual, he took the first (accidental) steps towards becoming the adopted ‘voice of his generation’. This single, a US release only, was the rallying cry of the 1960s and the unofficial anthem of the Civil Rights movement.

Rarest 1963 Columbia (US version) £20-£25


After the partial false start of his debut, The Freewheelin’… is an extraordinary leap in Dylan’s development as a major artist. With lacerating contemporary lyrics set to traditional tunes, it’s the album that announced him as a songwriting voice like no other. It contains three major protest songs: A Hard Rain’s A-Gonna Fall, Masters Of War and the near-biblical Blowin’ In The Wind.

Rarest 1963 CBS mono £60 / Latest 2017 Columbia £20


Dylan’s third studio album saw the scruffy troubadour still in full Woody Guthrie mode, and its fine collection of protest-heavy songs, for the most part, address contemporary social injustices (such as racism and poverty). The peerless title track, Only A Pawn In Their Game and The Lonesome Death Of Hattie Carroll remain as masterful now as they were crucially important back in the day.

Rarest 1964 CBS (mono) £60 / Latest 2017 Columbia £18


Having protested too much (literally), reluctant prophet Dylan shelved his social conscience and dug deeper to reveal himself as a romantic and a poet. Much to the vexation of the die-hard folkies, this resulted in an intimate, imaginative and rewarding multi-layered album. It Ain’t Me Babe, All I Really Want To Do and My Back Pages are among its many highlights.

Rarest 1964 CBS (mono) £60 / Latest 2017 Columbia £18


Dylan goes electric as he taps into the zeitgeist and delivers a Beat-style headrush of a single. The track so captivated John Lennon that the poor Beatle felt unable to compete as a songwriter. Bob’s famous cue-card-tossing version in D.A. Pennebaker’s Dont Look Back fly-on-the-wall flick is the precursor to the music video. All achieved in just 20 seconds over the two-minute mark.

Rarest £12


Bringing It All Back Home can be considered a transitionary album; it’s definitely groundbreaking and almost certainly genius. It’s also divided into two distinct halves: Side A sees Bob play loud for the first time – while Side B is a return to the acoustic sound (opening with Mr.Tambourine Man). Protest songs are now firmly a thing of the past, and Dylan’s increasingly cryptic material remains personal and introspective.

Rarest 1965 CBS (flipback sleeve) £60 / Latest 2017 Columbia £18


Just back from a gruelling, hecklesome tour of the UK, an exhausted Dylan angrily scrawled an epic 20-page piece of verse that he eventually condensed into the lyrics of what is his greatest song. Upon the release of this epochal 45, in just over six minutes of the most coruscating music that had ever been committed to vinyl, Dylan emerged as a fully fledged rock star.

Rarest 1965 CBS £12


Named after the road that runs from Dylan’s home state of Minnesota down to the Mississippi Delta, his sixth studio album is where Judas – sorry, Bob – goes all-out electric. With the help of bluesman Michael Bloomfield on guitar, the liberated Dylan finally puts the nail in folk’s coffin with an essential masterpiece of an album… although paradoxically, Desolation Row, the album’s sole acoustic track, almost steals the show.

Rarest 1965 CBS (mono) £60 / Latest 2017 Columbia £18


Recorded during the Highway 61 Revisited sessions, but held back and released as a non-album single, Positively 4th Street is a rocking, spiteful bitch-fest. The assumption is that this vitriolic 7″ slab of vinyl is targeted at the Greenwich Village scenesters who resented his new direction… he has a positively sharp tongue, that Dylan.

Rarest 1965 CBS £15


This non-album single is notable for being the first time The Hawks (later The Band) backed Dylan in the studio. The band’s chugging barroom blues drives the track along, while bitter Bob spits out a lyrically dexterous torrent of contempt. Dylan famously kicked folkie Phil Ochs out of his limousine for dissing the track.

Rarest 1966 CBS £18


Searching for what he described as that “thin, wild, mercury sound”, Dylan recorded this landmark double album in Nashville with a bunch of crack Music Row session musicians (Al Kooper and Robbie Robertson were also along for the ride). It was a genius move that produced a remarkably rich set of songs set in a dense country/blues soundscape. It’s nothing less than Dylan’s certified magnum opus.

Rarest 1966 CBS (mono, 8/9 photos on inner gatefold) £85-£90 / Latest 2017 Columbia £25


Dylan’s post-motorbike crash comeback album is a calm, reflective work that marks another shift in musical direction. It’s a departure from the multi-layered ramshackle electric R&B of his previous three albums; in its place comes a collection of original compositions with a pared-down country feel. If the category had existed at the time, it could happily be filed under ‘Americana’.

Rarest 1968 CBS (mono) £40 / Latest 2017 Columbia £18


What’s first apparent about this classic 1969 single is that it is sung in a low, warm-sounding croon rather than the abrasive nasal tone Dylan used on previous records. In typical myth-making fashion, he attributed the change to the fact he had recently quit smoking. Lay Lady Lay was written for inclusion on the soundtrack of Midnight Cowboy, but wasn’t submitted in time to make the cut.

Rarest 1969 CBS £8


Dylan’s final album of the 60s, a decade whose musical landscape he helped so radically to shape, saw him go full-on country. This charming curveball came complete with steel guitars, relatively straightforward, go-ahead songs and a memorable duet with Johnny Cash on opening track Girl From The North Country. Having alienated his adoring folk audience, he was now challenging his recently acquired rock fanbase.

Rarest 1969 CBS (mono) £40 / Latest 2017 Columbia £18


With his immaculate copybook blotted by the underwhelming Self Portrait, New Morning was released just four months later and went some way towards making amends. A partial return to form, the highlights include opener If Not For You; a sentimental love song which also appeared on George Harrison’s All Things Must Pass in the same year.

Rarest 1970 CBS £30 / Latest 2012 Columbia £18


Recorded after the New Morning sessions, this non-album single was produced by Leon Russell and is often regarded as the first tentative step towards finding a new sound. It’s certainly much more bluesy than the country-styled material that came before it. Although trying to fathom the true meaning of Dylan’s songs can be a futile pursuit, many believed it to be a statement about a desire to withdraw from public life.

Rarest 1971 CBS £8


After three years of relative inactivity, Dylan accepted a small role from director Sam Peckinpah in his movie Pat Garrett And Billy The Kid. He also wrote the music for the soundtrack – while the album was panned, it did produce this memorable single. Knockin’ On Heaven’s Door was Bob’s first hit for some time, and it also appeared in the charts for Eric Clapton and Guns N’ Roses.

Rarest 1973 CBS £8


Reuniting him with The Band, Planet Waves was Dylan’s first proper album in three-and-a-half years. It picked up where New Morning left off and denotes the final chapter in his country period. An overlooked gem, it may be modest in its scope, but it captures a domesticated Bob at his most relaxed and, dare we say, open-hearted. It was released in the UK on Island Records, and on Asylum in the US.

Rarest 1974 Island (pink rim) £25 / Latest 2004 Columbia £12


Dylan’s first official live-album release, Before The Flood celebrated his 1974 American tour with cohorts The Band. The double album showcases many of the greatest songs from his back catalogue, but far from being merely an exercise in nostalgia, the classic tracks are extensively rearranged and reinterpreted. It remains a fascinating, if not fractionally overblown, document of the times.

Rarest 1974 Island (gatefold) £20 / Latest 2014 Columbia £20


Ever the contrarian, the man himself maintains that his 1970s masterwork isn’t personal – yet the raw intimacy of this song cycle about a marriage on the skids suggests otherwise (especially as Dylan’s own marriage at the time was, yep, you guessed it, on the skids). There’s pain, heartache and savage name-calling (Idiot Wind) but there is also maturity and compassion. One of the great break-up albums – in fact, one of the great albums, full stop.

Rarest 1975 CBS £30 / Latest 2017 Columbia £18


Released in 1975, many of the songs were actually recorded in 1967 at houses in and around Woodstock in rural New York, where Dylan and The Band lived. The songs are loose, raw and rootsy, mixing up a charming cocktail of folk, country and blues. It captures Bob at his spontaneous, unpolished and mercurial best, and helped set the alt-country template.

Rarest 1975 CBS £30 / Latest 2017 Columbia £25


In 1975, Dylan unexpectedly returned to the protest song to tell the shameful story of Rubin ‘Hurricane’ Carter, a black boxer wrongly convicted of a triple murder. The powerful single, which could have passed as the speech for the defence, helped to raise national awareness of the case: Carter’s conviction was eventually overturned. Collectors will covet the picture sleeve.

Rarest 1975 CBS (picture sleeve) £10 / Latest 2015 Columbia £15

DESIRE (1976)

Any follow-up to an album as intense as Blood On The Tracks is going to sound relatively breezy in comparison, and that’s exactly what Dylan delivers with Desire. Second single Mozambique, for instance, is a decidedly poppy, picture-postcard of a song. It’s not altogether without its personal moments and closing track Sara is an emotional tribute to his soon-to-be-ex wife.

Rarest 1976 CBS £20 / Latest 2017 Columbia £18


Following the twin successes of Blood On The Tracks and Desire proved difficult even for Dylan, and Street-Legal will forever remain in their immense shadow. For some, the polished production is an issue, but the album still had its admirers. In the UK, it outsold both its illustrious predecessors to become his best-selling studio album.

Rarest 1978 CBS £20 / Latest 2010 Columbia £15


Dylan serves up yet another curveball to his long-suffering fans and this time, he’s not only found religion, but has also recorded a full-scale Christian rock album. The devout Slow Train Coming features Mark Knopfler on guitar (he had no idea born-again Bob had found God until he rocked up at the studio) and veteran producer Jerry Wexler. The album is bluesier and funkier than you might think.

Rarest 1979 CBS £18 / Latest 2015 Columbia £15


The 80s weren’t kind to Dylan, with his recorded output pretty sketchy at best. The exception, however, is Infidels, his first secular record since Street-Legal in 1978. Produced jointly by Mark Knopfler and the man himself, the temporary rekindling of the old magic means it is his strongest work since Blood On The Tracks. The legendary Sly And Robbie provide the rhythm section, and Mick Taylor contributes guitar alongside Knopfler.

Rarest 1983 CBS £18 / Latest 2003 Columbia £15


Moonlighting under the moniker Lucky Wilbury, a relaxed Dylan joined George Harrison, Roy Orbison, Jeff Lynne and Tom Petty to become one-fifth of late-80s supergroup The Traveling Wilburys. The project not only looked promising on paper, it sounded great on vinyl – and this entertaining debut was considered a commercial and artistic success.

Rarest 1988 Warner Bros £25 / Latest 2008 Rhino £15

OH MERCY (1989)

Daniel Lanois took the production gig on 1989’s Oh Mercy and U2’s knob-twiddler managed to coax Dylan out of his rut. It was by far the most consistent collection of songs he had written in a long while and was hailed as a minor triumph. Dylan had regained his love of lyrics and Lanois’ swampy production gave the songs an atmosphere in which to thrive.

Rarest 1989 CBS £15-£20 / Latest 2012 Columbia £15


With a train-wreck of a decade behind him, it was the right time for a reminder of Dylan’s genius, and first up was a five-album set containing rarities and unreleased works from the sessions for 1962’s Bob Dylan through to 1989’s Oh Mercy. It was a treasure trove of pure greatness.

Rarest 1991 Columbia (five-LP boxset) £150 Latest 2017 Columbia/Sony £55


Reuniting with Daniel Lanois, Time Out Of Mind was Dylan’s first release for seven years with original material. The double album proved to be a late-career triumph, surpassing all expectations of those who doubted he had any juice left in the creative tank. Dylan was now cast as a bitter, haunted bluesman singing soul-baring songs about death and loss. It was a persona that suited him well.

Rarest 1997 Columbia (double LP) £30 / Latest 2014 Columbia £22


Bizarrely, despite the title to the contrary, Vol. 4 of The Bootleg Series was recorded at the Manchester Free Trade Hall concert rather than the Albert Hall, hence the quotation marks. It’s a landmark document in the history of contemporary music; even the heckles are legendary (“Judas!”). It’s also a great live album, with seven acoustic tracks and eight electric.

Rarest 1998 Columbia (US version) £90


Daniel Lanois was deemed surplus to requirements here and Dylan took over the production duties himself. It was a shrewd move – his songs and the band sound great when unburdened by any production affectation. Bob’s raspy, weathered voice navigates across a range of styles important to him – blues, folk, swing, bluegrass and even rockabilly. It’s a major tour de force, from a revitalised icon having a ball.

Rarest 2001 Columbia £20-£25 / Latest 2012 Columbia £20


In 1975, The Rolling Thunder Revue – Dylan and an all-star cast, including Joan Baez, Roger McGuinn, Mick Ronson and T Bone Burnett – went on the road to promote the forthcoming release of Desire. It was an ambitious project. Getting all the musicians onstage at the same time was challenge enough, but as this live album reveals, the shows were a ramshackle yet thrilling ride.

Rarest 2002 Columbia (US version) £45-£50


Volume 6 of the illuminating Bootleg Series revisits Dylan’s all-acoustic past and the solo Bob is armed with nothing more than a guitar, harmonica and Joan Baez. This fascinating live performance was recorded just after the release of Another Side Of Bob Dylan and, while the protest songs aren’t yet a thing of the past, the new material does tip an arch wink at what was about to come.

Rarest 2002 Columbia (US version) £45-£50


Martin Scorsese’s documentary covers Dylan’s career, from his chubby-cheeked origins as a schoolkid in Minnesota through to being a frazzled balladeer on the verge of a motorbike crash. The soundtrack album is presented in strict chronological order and, as a result, illustrates just how fast he evolved from callow youth to world-renowned artist.

Rarest 2005 Columbia (US version) £35-£40


With flying visits to the roots of the American music styles of his distant youth, specifically blues and jazz, Modern Times is the companion piece to Love And Theft. Dylan’s artistic renaissance continues, the rasp from his throat he used to call a voice just about holds up, and Dylan is still a grinchy old sod capable of sparks of rare genius.

Rarest 2006 Columbia £20-£25 / Latest 2014 Columbia £20

ANOTHER SELF PORTRAIT (1969-71) (2013)

The Bootleg Series zooms in on the music recorded around the time of Dylan’s 1970 album Self Portrait, an album that was savaged by the critics on its release: Rolling Stone’s Greil Marcus famously started his review with: “What is this shit?”. This fascinating collection of sessions, demos and outtakes, which stretches to the New Morning period, reveals a much better album was somewhere to be had.

Latest Columbia 2013 £45


The original issue of The Basement Tapes back in 1975 barely scratched the surface. A CD-only boxset of the complete sessions contained 138 tracks, of which 117 were not previously issued – Bob and The Band must have really liked it down there in the basement. The triple-vinyl release, Basement Tapes Raw, is a distillation of the collection and is an endless wonder in its own scrawny-little-brother way.

Latest 2014 Columbia £75


Frank Sinatra is famed for the tone and timing of his vocal delivery – one of the greatest voices in contemporary music. At the end of a long career, Dylan’s voice resembles a gravel path bleached in the sun, but why should that prevent him from releasing an album of lesser-known Sinatra covers? Why, indeed. The album reveals itself to be a heartfelt, well-sung appreciation of the songwriter’s art.

Latest 2015 Columbia £20