The Making of Bob Dylan's Music Documented

Rare recordings from 1956-63 provide a wonderful insight into the early development of Bob Dylan's music

You could say Bob Dylan has had more Bootleg Series albums than hot dinners.

Speaking of which, his latest – Vol. 18 – is simply a feast! For it goes back, way back. Titled Bob Dylan’s Bootleg Series Volume 18: Through The Open Window, 1956-63, it covers exceedingly rare recordings from when he was a nobody in his mid-teens in Minnesota, to being a somebody in his early twenties in Greenwich Village, New York.

Few Dylanologists – let alone dedicated fans – would have speculated that such an unreleased treasure-trove still existed from this formative period.  Who would imagine that in those days so much material could have been recorded by an unknown singer-songwriter on such informal occasions? And this was an era of no mobile phones and recording apps!

So, what is new and not already in other bootleg volumes - both official and unofficial - and countless compilations?

Released by Columbia Records and Legacy Recordings, the catalogue division of Sony music, it features a massive volume – an 8CD, 139-track Deluxe set, with a hard-cover book and 100 rare pictures. There are also highlight editions, comprising 42 tracks on 2 CD’s and 4 LP’s. Of the 139 songs, 48 are listed as “never-before released” performances and 38 cuts categorized as “super rare.”

The set covers recordings at clubs, informal gatherings and jam sessions with fellow greats, as well as unheard Columbia outtakes. And a special feature is that it concludes with a previously unreleased recording - in its entirety - of Dylan’s phenomenal landmark concert at Carnegie Hall on October 26, 1963, when on the doorstep of fame at the age of 22. There was a six-track version released in 2005 and other songs from this Carnegie Hall show have popped up in various compilations.

Sony purchased Dylan’s recorded music catalogue – as opposed to his song-writing publishing rights – for an estimated $200 million in 2022. And it is hardly surprising that now is the time to cash in on their investment. For these early years cover somewhat the same period featured in the critically-acclaimed biopic A Complete Unknown, released in December last year.

The hype surrounding the extraordinary box set began in mid-September when a preview single “Rocks and Gravel” was released. It was one of several 1962 outtake from Dylan’s second album The Freewheelin’ Bob Dylan. And around the same time, several other tracks were available on streaming – providing a tantalizing tease for what was to come with the full release on October 31.

It was then when fans could finally hear what was obviously the first actual Dylan recording – an enjoyable 30-second snippet of Shirley and Lee’s “Let the Good Times Roll.” It took place on Christmas Eve, 1956, in a booth at the Terlinde Music Shop in St Paul, Minnesota. He was just 15 and playfully jamming around with a cousin and a friend. His second recorded song was “I Got a New Girl.” It is listed in this volume as “an informal recording,” and was made in his hometown of Hibbing in 1959.

Dylan arrived in New York on January 24, 1961. The inspiration for the trip was largely his infatuation with the legendary Woody Guthrie. He aspired to both meet and play for his folk hero and would do so within a couple of weeks of his arrival. And mixing in the Guthrie folk circles would prove a determining factor in signing a record contract by the end of his first year in the Big Apple. But it was not with any of the folk-specialist labels – all shunned Dylan.

It has been well documented how producer extraordinaire, Columbia’s John Hammond, signed Dylan largely on a whim when he first heard him playing harmonica at a rehearsal session with folksinger Carolyn Hester at her New York apartment in September 1961. (And, yes, there is a track, “I’ll Fly Away,” with Hester, illustrating the wide net cast in Vol. 18.) By the end of October, Dylan had signed with Columbia Records. So, the time-span covered in Through The Open Window, 1956-63 nicely segues around this significant event.

“Of that time and those places, this collection is just a fragment,” music historian Professor Sean Wilentz wrote in the set’s 125-page liner essay. “Even so, as an aural record of an artist becoming himself – or in Dylan’s case, his first of many artistic selves – the collection aims to collapse time and space, not as a nostalgic reverie but as a living connection between the past and the present, the old and the new, which are never as distinct as we might think.”

Central to Dylan’s early recognition were his appearances at Gerde’s Folk City, a music venue in the West Village of Manhattan, which was frequented by the likes of Pete Seeger, Joan Baez, the Clancy Brothers and John Lee Hooker. Dylan made his first appearance there on April 11, 1961 – supporting Hooker. And it was a gig at Gerde’s five months later – when he was opening for the Greenbriar Boys – which brought him his first-ever review. It was in the New York Times on September 29, written by esteemed folk/country critic Robert Shelton. No doubt this favourable top-of-page review – headlined Bob Dylan: A Distinctive Folk Song Stylist - further alerted Hammond to this promising new kid on the folk block.

So the inclusion in Vol. 18 of half a dozen tracks recorded in Gerde’s, in that pivotal year, provides a documented insight into the mind-boggling artistic development of Dylan in his first 12 months in NY. All the selections in the 1961 Gerde’s session - “See That My Grave Is Kept Clean” (Blind Lemon Jefferson), “The Girl I Left Behind” - (Traditional), “Pretty Boy Floyd (Woody Guthrie), “Railroading on the Great Divide” (Sara Carter) – are covers of popular folk standards.

Fast forward 12 months to another awesome Gerde’s gig and the Bob Dylan of Bob Dylan-fame is emerging. This provides a wonderful example of the rapid development of Dylan’s song-writing skills. Three of these five songs – “Honey, Allow Me Just One More Chance” (Harry Thomas/Bob Dylan), “Talkin’ New York (Bob Dylan), “Corrina Corrina” (Bo Carter), “Deep Allum Blues” (Traditional), “ Blowin’ in the Wind” (Bob Dylan) – were either a co-write or written by Dylan. He actually made the live debut of his most influential song, “Blowin’ in the Wind,” at Gerde’s, though it is unclear if this is the one on Vol. 18. The classic would be released nearly a year later on Freewheelin’.

All but two of the 13 tracks on Freewheelin’ were Dylan originals (there was a co-write and a traditional). Most would become classics. While the album was actually released on May 27, 1963, some songs were recorded as early as April the previous year. “Blowing in the Wind” was among them. It was The Freewheelin’ Bob Dylan which would put him on a global stage - the debut album, Bob Dylan, hardly paid for itself and indeed it had led some in the industry to label Dylan as “Hammond’s folly.”

Also fascinating in this early compilation are the recordings made outside New York. There are a handful from before he arrived - four in Minnesota and three in Madison, Wisconsin, where he actually first saw Pete Seeger perform. And it is obvious from Vol. 18 that on occasions he would return to his home state. The most notable of these visits was in mid-1961 when Dylan recorded several songs at Bonnie Beecher’s apartment in Minneapolis. Some cropped up on early bootleg albums and one of the finest of those sessions, “Death Don’t Have No Mercy,” is included in Vol.18.

If the tracks are listed in chronological order, then - as a quirky aside - the first songs actually recorded after his arrival in the big smoke were not in New York, but in neighbouring New Jersey. Woody Guthrie’s classic “Pastures of Plenty” and Scotty Wiseman’s old-timer “Remember Me (When the Candle Lights Are Gleaming)” are listed as “informal recordings” made by Dylan in early ’61 at East Orange in Essex County, NJ. It was a home of folk enthusiasts Bob and Sid Gleason, and where he had first met Guthrie. These two songs were included on The East Orange Sessions 1961 when it was released in 2016 as a compilation of 21 tracks, recorded at least six months before his signing with Columbia - when Dylan was trying to impress influential folkies.

And though “Remember Me” was among the archival tracks in the 2016 release, it is so creatively quaint it must rank as one of the most distinctive songs of this time-span.

The ‘56-‘63 compilation also recognises his first travels outside the U.S. He crossed the border to Montreal in July 1962 to play at The Finjan Club. It has become known as one of his most commanding performances and was officially released in 2012 on Finjan Club: Montreal, Canada July 2nd 1962 (Live) . There are five of the Finjan tracks in Vol. 18, the standout is an early version of “Let Me Die in My Footsteps,” one of his first protest songs. Later in the same year he was invited to London by the BBC for a cameo role in the TV play Madhouse On Castle Street and one song, “The Ballad of the Gliding Swan,” from the production makes this list. It is a sparse, one-minute rendition.  For many, his London visit – where he was exposed for the first time to the Celtic-Folk tradition – was yet another determining factor in his rapid song-writing.

Dylan scholars have long regarded the 1963 Carnegie Hall concert as pivotal to his early success. The full gig - 19 songs – was recorded on October 26 and all have been released in dribs and drabs over the years. Six were included on a 2005 EP, Live at Carnegie Hall 1963, and four other songs were released on the numerous Dylan compilations. Then in 2013, the remaining nine songs were issued on a European-limited vinyl release, The 50^th Anniversary Collection 1963.

But Volume 18 provides the first opportunity to hear the famous concert in its entirety – as originally intended. The Carnegie gig constitute discs 7 & 8 of the Deluxe set and Dylan’s somewhat candid introductions to several songs are included. Prior to this appearance at Carnegie Hall, Dylan had released just two albums, Bob Dylan & The Freewheelin’ Bob Dylan, with the third, The Times They Are a-Changin’ - largely recorded but not released until three months later. The significance of albums 2 & 3 was that all the songs – save one traditional on Freewheelin’ – were Dylan compositions, or co-writes. So, the Carnegie appearance provided him with an opportunity to prove to his aspiring – mostly young – fans that he was now a significant song-writer and not just a Greenwich Village folk interpreter.

All 19 songs on the concert setlist were written by Dylan, though all but five were still to be released. While the audience may have been hearing many of these songs for the first time, some of the unreleased songs had already been included in earlier concert setlists. The best example is “With God on Our Side” which he had introduced at a break-through concert at New York’s Town Hall on April 12, 1963. And it had made an immediate impact. When, in his Carnegie Hall introduction, he declared “Here’s a song With God on Your Side,” it was met with spontaneous applause.  The random clapping continued during the song, after such jaw-dropping stanzas like: Though they murdered six million/In the Ovens they fried/The Germans now too have God on their side

A rousing eight-minute arrangement of “A Hard Rain’s A-Gonna Fall’ – introduced as “a hard rain’s gonna fall means something’s gonna happen” – deserved the thunderous applause. But perhaps Dylan’s most striking delivery on the night came, not with a political song, but with the mystical, Celtic-influenced, lament-on-life “Lay Down Your Weary Tune” - a song he would seldom sing again. He had recently written it at Joan Baez’s house in Carmel California. It would be recorded for the upcoming Times They Are a-Changin’ but it never made the album and would not be released until 1985 on the Biograph box set.  The Byrds would give it early prominence on their 1965 album Turn, Turn, Turn. And in 2005, Columbia thought enough of the Carnegie Hall version to list it in the chosen six on the concert EP.

Listening to Dylan deliver this recital back-to-back is utterly compelling, given that he was introducing a mass audience to songs which would have such an impact on modern music. So what makes it all somewhat mystifying is why Columbia did not release the full concert earlier, instead of drip-feeding the assorted songs through years? Yes, there have been more than 20 Dylan-live albums – including the infamous “Judas” concert at the Manchester Free Trade Hall in May 1966 during his folk-to-electric transition. But none personify his true coming of age as a unique and influential singer-songwriter than Carnegie Hall 1963.

Outtakes from studio sessions can offer an intriguing insight to an artist in the formative stages of creative development. Dylan was no exception in this early folk period. And the selection of outtakes in Vol.18 nicely illustrates this.

There were four outtakes from Dylan’s self-titled debut album, recorded in three two-hour sessions on November 20 and 21, 1961. Three make it to Vol.18 – “House Carpenter,” “He Was a Friend of Mine” and “Ramblin’ Round.” The first two were traditional songs and the third “Ramblin’ Round,” a Woody Guthrie song which made it to a 2014 Dylan compilation and must rank among his best covers of the folk legend.

By the time he began recording Freewheelin’ in June 1962, Dylan was writing up to five songs in a single night. So, it is no surprise that 11 of the 13 tracks on this second album were his own compositions and, not unexpectedly, there were more than 20 outtakes, once the final album-list was eventually agreed upon. Five of these outtakes make Vol.18, the most significant being “The Ballad of Hollis Brown,” the tragic tale of a South Dakota farmer who falls on hard times and kills his family. The song was re-recorded in 1963 for The Times They Are A-Changin’. There were several live versions – with variations – between ‘62-64 and the live track listed on Disc 7 is from the October Carnegie Hall concert. It provides a nice comparison to the original studio recording on Disc 4.

The ten songs on this third album are all attributed to Dylan, though two were variations of traditional Celtic-folk songs. And, as in Freewheelin’, there was a bundle of outtakes. Five make it to this compilation, the most appealing being “Moonshiner” and the grim “Seven Curses.” Both would surface on The Bootleg Series Volumes 1-3. There is also an intriguing “alternate take” of “Boots of Spanish Leather,” a Celtic-influenced love classic inspired by his parting from girlfriend Suze Rotolo. And again, this take can be compared to the version on the Carnegie Hall setlist.

The compilers chose to end Vol.18 in late 1963, with the Carnegie Hall event, which begs the question as to why it wasn’t extended through 1964 when Another Side of Bob Dylan was recorded. But much happened – both social and political - across America in 1963. So, it’s not surprising that two of the eight discs are devoted to material recorded during that year. Dylan, encouraged by Rotolo, a left-wing activist, was on the fringe of this social upheaval and now writing political songs.

And this era is nicely proportionally reflected in Vol.18.

In July, Dylan and Seeger headed to Greenwood, Mississippi, to take part in a black-voter registration rally. It was his first experience of southern segregation. And it was at a rally near a cotton field that he debuted “Only A Pawn In Their Game.”  It would be regarded as an historic performance, captured on film. But some intensive remastering was required  for this track, which is included on disc 6, along with two other recordings from the rally - “Blowin’ in the Wind” and an introduction by the event organizer.

A few weeks later, Dylan made his debut at the Newport Folk Festival. Seeger and Baez were also on the bill. This volume includes one Dylan solo at the event, “North Country Blues,” and three support-performances – “With God on Our Side” (with Baez), “Playboys and Playgirls” (with Seeger) and “Blowin’ in the Wind” (with Baez, Peter, Paul & Mary, The Freedom Singers, Seeger).

Then on August 28 came the Civil Rights March on Washington - most significant event of the year before the John F. Kennedy assassination.  Dylan and Baez both joined the 200,000  marchers at the D.C. event. Dylan would perform “Only a Pawn In Their Game” and “Blowin’ In The Wind” by himself. Neither of these are included, but his duet with Baez of “When the Ship Comes In” is in this collection, along with the introduction by actor and activist Ossie Davis. By the end of 1963 Dylan had become more elusive, saying he felt manipulated by the protest movement. So, it seems appropriate that Vol.18 ends at the close of ’63.

There is no doubt that the real value of Vol.18 lies in the full 139-track Deluxe set rather than the CD and LP highlights – if only to get access to all the 48 cuts marketed as never before released.  And, of course, the abbreviated versions do not include the Carnegie Hall concert in its entirely, nor do they have many of the appealing song-introductions and banter. But the compilers have wisely chosen the “teenage” recordings - obviously never-heard tracks - to open all versions,  

No matter what the status of the 139 songs, this volume is itself a documentary in music. And a most historic one. Project compiler Wilentz said it best when he told Rolling Stone: “He (Dylan) was discovering himself, discovering new stuff. He was insatiable. ” He added “That’s the other thing I think we want to put across, is that a genius, is not born, genius is made, and it’s made by the genius himself. You can hear Dylan on a lot of the cuts here working very, very hard at mastering his craft.”

Though, there is something ironic about this phenomenal collection. For we hear a lot of Dylan chatting between takes, whether it be jibes during a concert, questions between studio tracks or witting remarks playing in front of friends. All allow the listener to eaves-drop on Dylan's sometimes-cocky, sometimes-endearing character in the early '60's.

Fast forward 60-odd years and Dylan, now 84, is still performing. But these days, he has a paranoia about fans taking pictures. So, he wears a hoodie onstage, and hides behind a grand piano or music stand. In fact, he seldom engages with audiences at all.

The times they have a-changed. But the wonderful folk music remains.

Paul Cutler

Editor Crossroads - Americana Music Appreciation