Bob Dylan’s Bootleg Series albums… ranked!

The unparalleled exemplar of back catalogue management…

What record companies back then used to do with their artists’ back catalogues was wait until enough of the artists’ records had charted and then re-release them all again as Greatest Hits collections. When the artists started to run out of hits, there were Best Of compilations.

Either way, content was re-cycled, with little annotation and nothing so grand as contextualisation, beyond in those days an occasional sleeve note from a fan on the music press (“… some of the best music known to mankind…”), a cheery note from a band PR (“…the boys hope you ‘dig’ listening to these ‘hits’ again as much as they do…”) or for the heads a trippy endorsement from John Peel (“…the sad and scattered leaves of an older summer…”).

Fans turned out to have an unusual appetite for music they’d already heard, had bought on release and seemed happy to pay for again in re-packaged form. The best-selling American album of the last century was The Eagles’ Their Greatest Hits (1971-1975), released in 1976. It was a cheap and easy way for record companies to make lots of money. It was also cynical, exploitative and unimaginative. Everything you’d expect from a major label, really.

This all changed in 1985 with the release of Bob Dylan’s Biograph. On its original release, it was a 5LP or 3CD retrospective, 53 tracks covering 1962-1981, handsomely packaged with rare photographs, a Dylan interview and his own track-by-track commentary. Of them, 18 were previously unreleased, three of them available until now as singles. Biograph wasn’t so much an anthology as a monument. Pretty soon everyone had something similar in the works. Archives were pillaged. Rehearsal tapes exhumed. You could build a couple of full-scale pyramids from the number of boxsets since released and still have enough left over for a life-size model of the Sydney Opera House.

The Bootleg Series has continued to be the unparalleled exemplar of back catalogue management, highlighting historic albums, tours, concerts, listed here in an order that owes less to scientific calculation than personal preference.

15 Travelin’ Through – The Bootleg Series Vol 15 1967-1969

A 3-CD set covering John Wesley Harding, Nashville Skyline, 1969 sessions with Johnny Cash and his band, featuring Carl Perkins, Dylan’s appearance on The Johnny Cash Show, a couple of out-takes from Self Portrait and a great session with Earl Scruggs. Dylan knew exactly what he wanted on John Wesley Harding. The whole thing was recorded in nine hours. The seven alternative versions included here from the sessions varied little from the album versions, apart from a spritely “I Pity The Poor Immigrant” with a different tune. The Nashville Skyline out-takes are similarly scant. The Cash Sessions are to say the least informal, Dylan and Cash for the most part sounding like old pals moved to song by drink. For all the fun they evidently had, what we were left with sounded like an opportunity missed.

14 The Witmark Demos: 1962-1964 – The Bootleg Series Vol 9

The 47 tracks on this 2-CD set were recorded by Dylan between January 1962 and January 1964 as song-writing demos for his first two music publishers, Leeds Music and M Witmark & Sons, Dylan accompanied by either guitar or piano. Many of them appeared on subsequent Dylan albums, some of them era-defining classics, including “Blowin’ In The Wind”, “A Hard Rain’s A-Gonna Fall”, “Masters Of War”, and “The Times They Are A-Changin’”. There were 15 tracks that remained unheard for nigh on 50 years, strikingly among them “The Ballad Of Emmett Till”, dropped from his debut album, and a lovely version of “Tomorrow Is A Long Time”. Listening to these tracks, you imagined Dylan as the boy he was, writing “Blowin’ In The Wind”, that bombshell moment. Could he possibly have imagined the impact these songs would shortly have on the world and what would become of him then?

13 Bob Dylan Live 1964 – The Bootleg Series Vol 6

The complete set on two CDs from Dylan’s Halloween concert at New York’s Philharmonic, Dylan caught in transition from inspired young folkie, the darling of that night’s crowd, to the yet more challenging visionary of Bringing It All Back Home, when he would write songs that didn’t make hm feel so much like a hack songwriter at an agit-prop Brill Building turning out tunes to be sung on Civil Rights marches, sit-ins and anti-war demos.

Dylan sings confidently throughout, usually loudly, and at his most piercing on nearly every track. A distance between singer and song was sometimes suggested. It’s not at all that he sounded distracted, the performances were first-rate and committed. It was more that what he was playing wasn’t the new music he could hear in his head, although “Mr Tambourine Man”, “It’s Alright Ma” and “Gates Of Eden” were in the set list, hints of what came next.

12 Trouble No More 1979-1981 – The Bootleg Series Vol 13

Slow Train Coming, the first of Dylan’s so-called Born-Again trilogy, was a great success, selling more in nine months than Blood On The Tracks sold in a decade. Dylan was not yet regarded as a demented Bible-thumper. That reputation came with the shoddily recorded Saved and the self-sabotaged Shot Of Love. Fans deserted him like they were fleeing a burning building. Contemporary bootlegs like Knoxville Grail suggested, however, that the live shows from the time were a blast, powerful reworkings of songs sometimes shabbily rendered on recent albums. Over eight discs and a bonus DVD, Trouble No More reinforced that impression with 100 previously unreleased tracks, culled from rehearsals, soundchecks, concerts and studio out-takes. For the less committed, there was a handy 2-disc version.

11 Springtime In New York 1980-1985 – The Bootleg Series Vol 16

This 5CD, 57-track set focused on Dylan’s three early-80s’ albums, Shot Of Love, Infidels and Empire Burlesque, all of them shadows of the albums they could have been. Shot Of Love was largely panned on release, but what a different reception it might have had if Dylan hadn’t jettisoned three key tracks, Groom’s Still Waiting At The Altar, Angelina and the epic Caribbean Wind or any of the cover versions on CDs 1 and 2, recorded during album rehearsals, including a sensational take on The Temptations’ I Wish It Would Rain.

With producer Mark Knopfler’s digital trickery thankfully redacted there were glimpses on CDs 3 and 4 of a different kind of Infidels, with fabulous versions of Jokerman, Blind Willie McTell and Foot Of Pride. Similarly, with the deft elimination of Arthur Baker’s era-specific production effects  on Empire Burlesque, CD5 presents glorious versions of I Remember You, Emotionally Yours and When The Night Comes Falling From The Sky, on its way to becoming the barnstorming take recorded with members of The E Street Band that appeared on The Bootleg Series Vols 1-3. The jewel here, though, was New Danville Girl, later reworked in blockbuster style as Brownsville Girl on Knocked Out Loaded.

10 No Direction Home: The Soundtrack – The Bootleg Series Vol 7

A 2-CD set compiled to coincide with the Martin Scorsese documentary that followed Dylan from 1961 to 1966. The set followed the film’s chronology. From Gerdes Folk City to the Albert Hall; “A Song For Woody” to “Like A Rolling Stone”. Along the way, Dylan was transformed almost from scene to scene. Fresh-faced hobo folkie. Gaunt-faced protest singer. Tab-collared hepcat. Almost the last time we saw him in the film, just before the final date of the 1966 world tour, he was pale, trembling, done in. As likely to fall off his chair as a motorbike. There were gems galore. A Newport ’64 version of “Chimes Of Freedom” and out-takes from Highway 61 Revisited and Blonde On Blonde alone made it essential.

9 Fragments – Time Out Of Mind Sessions (1966-1977) – The Bootleg Series Vol 17

1997’s Time Out Of Mind raised the curtain on Dylan’s extraordinary third act creative renaissance, although fans were divided about the noirish mugginess of Daniel Lanois’ original production, about which Dylan also evidently had misgivings. This 5CD boxset included a remix of the entire album that endeavoured to strip it of what some claimed was Lanois’ murkier studio atmospherics, making it sound closer to the albums that immediately followed, 2002’s “Love And Theft” and 2006’s Modern Times.

The music lost some of its primordial mystery in the process but highlighted anew the singular majesty of tracks like “Tryin’ To Get To Heaven”, “Not Dark Yet”, “Make You Feel My Love” and “Highlands”. There were two discs of alternative takes from preliminary sessions with Lanois, including a striking country soul version of “Not Dark Yet”, plus a largely sensational live disc. Disc 5 recycled tracks that had already appeared on Tell Tale Signs: Rare And Unreleased (1989-2006) – The Bootleg Series Vol 8.

8 Another Self Portrait – The Bootleg Series Vol 10

In one version a 2-CD set, with 35 tracks from 1969-1971 and covering three Dylan albums, Nashville Skyline, Self Portrait and New Morning. Among them were good alternative cuts of songs from the first and third of those albums. Mostly, though, the set was an attempt to rehabilitate Self Portrait, a double album, covers of mainly C&W and pop standards that on release had appalled nearly everyone. Stripped back versions of some of these tracks were especially welcome on the updated Bootleg Series version. But the real revelation was nine previously unheard versions of old country and folk favourites from the Self Portrait sessions, including a sublime reading of the traditional “Pretty Saro” and a quite magical “Tattle O’Day”. The deluxe edition was a 4-CD set adding a revelatory full account of Dylan’s appearance with The Band at the 1969 Isle Of Wight festival.

7 Bob Dylan Live 1975, The Rolling Thunder Revue – The Bootleg Series Vol 5

Apart from two Rolling Thunder tracks on Biograph, the only record of Dylan’s fabulous Bicentennial caravan prior to this 2-CD set was his 1976 live album, Hard Rain, recorded on the unhappy second leg of the tour, the one Dylan played to pay off the production costs of Renaldo & Clara. The hats and scarves were gone, the music mostly sour.

Live 1975 was a 22-track compilation, culled from tapes of five concerts professionally recorded by a mobile unit on the tour’s first leg, assembled to run as if according to the show’s set list. It was thrilling stuff. “Tonight I’ll Be Staying Here With You”, with re-written lyrics and a rampaging new arrangement, “A Hard Rain” recast as a storming roadhouse blues, many more. For the real beef, however, you needed the 14CD The Rolling Thunder Revue: The 1975 Live Recordings, two discs of rehearsals, 10 from shows, one of rarities.

6 The Basement Tapes Complete – The Bootleg Series Vol 11

Seven songs that Dylan and The Band recorded in the summer of 1967 in Woodstock that would enter legend as The Basement Tapes appeared in 1969 on Great White Wonder, rock’s first bootleg. In 1975, Robbie Robertson’s self-serving compilation of tracks from those sessions added overdubs and a bunch of later Band tracks, recorded long after the doors of Big Pink were closed. Fans had to wait 40 years, however, for The Basement Tapes Complete, a 6CD set.

Five collected all the 1967 tracks logged by Garth Hudson, the other separately discovered tracks. It was on the whole mind-blowing stuff, Dylan and The Band blowing through old favourites, before getting stuck into the vast phantasmagoria of Dylan’s new tunes. Most of the songs on CD3 and CD4 were inevitably familiar – so many big hitters! – but elsewhere on the set the legendary “I’m Not There”, a whisper as much as a song, finally got an official release.

5 Tell Tale Signs: Rare And Unreleased 1989-2006 – The Bootleg Series Vol 8

In its box set iteration, a 3CD set featuring 39 rare and unreleased tracks. They were mostly from the sessions that produced Oh Mercy and Time Out Of Mind, plus two startling Modern Times alternative takes, eight live tracks, a first hearing for two songs from unreleased 1992 sessions with guitarist David Bromberg and a marvellous duet with Bluegrass icon Ralph Stanley. Three tracks were retrieved from film soundtracks, including the epic “’Cross The Green Valley”. The set overall was awash with evidence of the myriad ways Dylan sees a single song, his determination even in the studio to repeat himself as little as possible, re-takes serial re-imaginings rather than an opportunity for tweaking and refinement. It was easy to feel swept away by it all.

4 More Blood, More Tracks – The Bootleg Series Vol 14

There were already eight previously unreleased tracks from the original New York sessions for Blood On The Tracks available across The Bootleg Series. Then this arrived, 87 tracks in its Deluxe Edition, spread over five CDs, with everything recorded in New York and the five tracks re-recorded in haste in Minneapolis that appeared on the album released in January 1975. Six hours of musical in all. Listening to the songs as they develop, take shape via constant on-the-hoof revisions, with and without other musicians, was like eavesdropping on genius.

Like looking over Sam Peckinpah’s shoulder as he assembled the final cut of The Wild Bunch, Robert Lowell adding the last words to For The Union Dead, Pynchon putting a full stop to Gravity’s Rainbow or Phil Spector applying the finishing touches to “You’ve Lost That Lovin’ Feeling”. You felt like a witness to a masterpiece being assembled from rough beginnings to final triumph.

3 The Cutting Edge 1965-1966 – The Bootleg Series Vol 12

The accelerated pace of Dylan’s transformation from strumming folkie to full- blown far-out rocker was documented in pretty much its available entirety on this session-by-session account of the making of the three albums he made in 18 months, between January 1965 when he started Bringing It All Back Home, through Highway 61, to the morning in March 1966 when he walked out of Nashville’s Studio A after the final 13 hour session for Blonde on Blonde, a couple of months shy of turning 25.

It remains the most lavishly packaged of the Bootleg Series releases, available as a 5000 limited edition 18-CD set with 379 tracks, roughly the equivalent of 40 albums, that took longer to listen to than it took Dylan to record Bringing It All Back Home. The Deluxe Edition had a more modest 122 tracks. A 36-track CD, The Best Of The Cutting Edge was a reasonable taster.

2 Bob Dylan Live 1966: The “Royal Albert Hall Concert” – The Bootleg Series Vol 4In

Dylan’s 1966 world tour was a nightly contest between the artist and fans made angry and perplexed by his new music. Loud electric blues for the most part, not a Scottish ballad or protest song in sight. English crowds were especially vocal in their disapproval. Things came to a head on May 17, 1966, at a concert at Manchester’s Free Trade Hall, for years thought to have been recorded at London’s Royal Albert Hall, a bootlegger’s mistake. The acoustic first half of the show was well enough received, the audience listening politely to even recent songs like “Visions Of Johanna” and “Mr Tambourine Man”.  After an interval, Dylan and The Band plugged in, blasted off. Large parts of the crowd recoiled. There was slow-handclapping, booing, a notorious cry of “Judas!” Dylan and The Band replied with some of the most brain-shredding live rock music ever heard. Play fucking loud, indeed.

1 Rare And Unreleased 1961-1991 – The Bootleg Series Vols 1-3

Six years after Biograph, the Bootleg Series introduced itself with a 3-CD set, released around Dylan’s 50^th birthday and featuring an extraordinary 58 previously unreleased tracks. What a haul it was! Many of the tracks would have been crowning achievements in the careers of most other songwriters and you wondered again at the contrarian whims that had consigned them to the archives, that dead place.

The breadth and quality of the songs was breath-taking and for the number of top-tier previously unavailable Dylan material it collected, the set remains unbeatable. It reminded us from the start that Dylan’s habit of leaving key tracks off his albums started early, with a dramatic version of the traditional ballad “House Carpenter”, dropped from his first album. Nearly 30 years after it was replaced on Freewheelin’ by the just written “A Hard Rain’s A-Gonna Fall”, we finally heard “Let Me Die In My Footsteps”. There were tracks everywhere making their official debuts that made your head spin. Fabled cuts like “Walls Of Red Wing”, “Farewell, Angelina”, “No More Auction Block” and “Seven Curses”, “I’ll Keep It With Mine”. Alternative versions of “Subterranean Homesick Blues” and “It Takes A Lot To Laugh, It Takes A Train To Cry” and songs from Blood On The Tracks.

CD3 was astonishing in itself, every track a back-of-the-net match winner. The abandoned Shot Of Love masterpiece, “Angelina”; “Someone’s Got A Hold Of My Heart”, an early version of “Tight Connection (To My Heart”) from Empire Burlesque; the E-Street Band version of the same album’s “When The Night Comes Falling From The Sky”, the raging Infidels out-take “Foot Of Pride”. At last, the hallowed “Blind Willie McTell”, dropped from Infidels. The collection ended with the five-minute fever dream of “Series Of Dreams”, a track Daniel Lanois had desperately petitioned Dylan to include on Oh Mercy, Dylan having none of it. For once, it was an argument you wished Lanois had won. Perhaps the most remarkable thing about it all was the feeling that there was a lot more of this to come. That there were many more tracks, unheard, waiting to be discovered, dusted off and offered to the world.