Bob Dylan: Through The Open Window – The Bootleg Series, Vol. 18 1956-63

(Columbia Records / Legacy Recordings)

CD | LP | DL

Released on 31 October 2025

PRE-ORDER HERE

Through The Open Window is the latest chapter in Bob Dylan’s Bootleg Series, this time covering the period 1956-63. Serving as a perfect accompaniment to the recent Dylan biopic which covered the period 1961-65, this is another vast collection of songs from the archives which oversees his transformation from a rocker inspired by Little Richard to an ardent folkie inspired by Woody Guthrie and covers the period during which Dylan started to emerge as one of the greatest and most poetic lyricists in the world of music as we know it.

It has now been almost three years since the last release in Dylan’s infamous Bootleg Series and naturally the speculation has continued to work in overdrive in anticipation of what might be coming next. In the interim at least we have seen the release of The 1974 Live Recordings (reviewed here) and The Complete Budokan 1978 (reviewed here), collections which have kept the worldwide Dylan community happy to varying degrees of success. But now we finally get the release of the next chapter in Volume 18, entitled Through The Open Window, which covers the period 1956-63, confounding much of the speculation which focused on later periods of Dylan’s thankfully never ending career.

Reflecting back a few months, there is little doubt that the release of the Bob Dylan biopic A Complete Unknown on 25 December 2024 sparked a significant resurgence in interest in this great artist’s life and work, not just for the worldwide fan base that continues to clamour for anything previously unheard or unseen in relation to Dylan, but also for a new and potentially younger audience who had little or no appreciation of his work, legacy or enduring appeal. Covering the period from Dylan’s arrival in New York in early 1961 through to his controversial electric performance at the Newport Folk Festival in 1965, the film’s impact was clearly aided by Timothée Chalamet’s remarkable portrayal of Dylan both in life and performance.

The film’s success was further subsumed in its immersive exploration of Dylan in the early 60s as well as his enigma, showing how his artistic drive and struggle with fame were both revolutionary and frustrating for those around him. Through The Open Window serves as a very effective accompaniment to the film, covering his early and most formative years in which, for the most part, he was performing other artists songs and building on a huge folk music legacy which were to fuel Dylan’s fire for many decades to come.

Through The Open Window comprises an 8 CD deluxe set which includes 139 tracks, of which around 40 have never before been released, a figure which will no doubt ignite yet more debate within the Dylan fan base given the complexity of Dylan’s extensive officially released back catalogue. It also comes with a hardcover book with a 125 page essay by writer, author and historian Sean Wilentz, documenting those times together with over 100 rare photographs. The 2CD and 4LP highlight editions include 42 tracks. It’s overall aim is to tell the story of Dylan’s emergence and maturation as a songwriter and performer, from Minnesota through to the Greenwich Village bohemia in the early 1960s. The collection includes rare Columbia Records outtakes, recordings made at club dates, coffee houses, in tiny informal gatherings, in friends’ apartments, and at jam sessions in long-gone musicians’ hangouts, all from brand new tape sources.

As depicted in the film, Dylan arrived in New York on 24 January 1961, heading almost immediately for the hotbed of coffee houses and cafes in Greenwich Village which housed the stages on which so many new and established folk artists were plying their trade. Dylan wasted no time in getting to know everyone who was anyone in the music business and brought with him a wealth of both talent and finely honed knowledge, both from his extensive reading and from listening to a huge catalogue of songs that were to shape his future. A quick scan of the track listing on this collection makes it very clear that a good deal of this song catalogue is represented here within some rare and obscure performances which predate his arrival in New York.

The wealth of known recordings of early Dylan in existence is well documented, and some may feel is under-represented in this release – more on this a bit later – but then again there are limitations on the extent of any archive release to make it both realistic and affordable. As Sean Wilentz explains within his essay, “Of that time and those places, this collection is just a fragment. 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.”

Disc 1 starts with what is considered to be the earliest known recording of a then rock’n’roll obsessed Dylan who made his first ever acetate on Christmas Eve 1956 with his band The Jokers. Unfortunately we only get a short segment of Let The Good Times Roll extracted from a Little Richard inspired medley of songs which is believed to be around 8 minutes long in total. Maybe one day…..but perhaps a big missed opportunity regardless of its rough and ready sound quality. Fast forward to the next song I Got A New Girl from May 1959 and this home recording in decent quality immediately shines a light on Dylan’s transformation from rocker to folkie which continues to develop through a whole series of previously unreleased recordings running up to October 1961.

The recording quality on these early takes is remarkable given the equipment that would have been available and the enduring spirit of Woody Guthrie sparkles both through Woody’s own songs and many of those that he had popularised in the years leading up to that time. There is an early take of San Francisco Bay Blues from Dylan’s own home in 1960 and a somewhat pedestrian version of Song to Woody, a song which would appear on Dylan’s debut album, together with an always hilarious rendition of Talkin’ Bear Mountain Picnic Massacre Blues from New York’s Gaslight Café in 1961. We also get a great recording of three of Woody’s songs performed by Dylan made when visiting friends in Wisconsin, highlighting an artist who was in the process of finding his new self. By the time we approach the latter part of this disc, including a short set from Gerdes Folk City, we venture very much into excellent sound quality.

For the more die-hard fans of Dylan’s early work, one glaring omission from this period is the lack of any songs from the known recordings which took place at the home of Karen Wallace in Minnesota in May 1960 which allegedly include some songs performed in Dylan’s unique Nashville Skyline style vocals…now this sounds like a real treat to enjoy…..someday. And there is also an alleged recording of an infamous performance by Dylan at Hibbing High School which has yet to see the light of day…..again, maybe one day.

The sound quality on disc 2, all of which derives from 1961, remains excellent throughout starting with a live performance from the Carnegie Chapter Hall on 4 November, Dylan’s debut solo show. This includes an early take on Gospel Plow, another song featured on Dylan’s debut album, Woody Guthrie’s classic Your Land Is My Land and the previously unreleased murder ballad Pretty Polly. More songs exist from this performance, as they do for many other shows featured on this collection, but room clearly precludes their inclusion. Some interesting unreleased studio outtakes from the Columbia Studios include songs like Man Of Constant Sorrow, You’re No Good and Ramblin’ Round, and pristine recordings from the Bonnie Beecher sessions include a very early take on Baby, Let Me Follow You Down.

Disc 3 largely covers live and session recordings from the earlier part of 1962 thereby straddling the release of Dylan’s self-titled debut album which came out on 19 March. Again, the sound quality is excellent throughout with the only exception of the previously unreleased home recording of Talkin’ John Birch Paranoid Blues, another amusing composition which has its own checkered history through its deep political references to communism. This was one of a number of songs that were removed from initial pressings of Dylan’s second studio album, Freewheelin’ With Bob Dylan.

There is most definitely a blues theme running through these sessions, noting the inclusion of songs like Wichita, It’s Dangerous, Corrina Corrina and Deep Ellum Blues, with the spectre of Big Joe Williams looming large. The inclusion of the interesting Midnight Special sessions is also worthy of note before we venture into a live set from Gerdes Folk City and then studio sessions in stunning quality which would lead up to Dylan’s second album, including songs like Rocks And Gravel which was another song removed from initial pressings of this album.

The Freewheelin’ studio sessions undertaken in the latter half of 1962 continue throughout Disc 4, all of which have been previously released in various forms but are at least in chronological order here with blues still running as a theme through early cuts of the likes of Baby, Please Don’t Go, Worried Blues and his very own Bob Dylan’s Blues. The previously unreleased material includes an impromptu version of the later verses of Woody’s This Land Is Your Land and Dylan’s first ever rendition of Long Time Gone, both from session recordings at the home of Dave Whitaker. It is in this period when Dylan’s own compositions finally come to the fore in his output, building on the strong folk legacy within all his previous performances and recordings, including stunning takes of Hard Rain and Don’t Think Twice at Gerdes.

Disc 5 takes us through the early part of 1963 right up to when Freewheelin’ was released on 27 May. These recordings are mainly sourced from home or live sessions, most of which have been released previously in various forms but again presented in excellent quality, allowing the commitment to the art of folk singing displayed by Dylan to shine through so brightly. Of particular interest here is a clip of The Ballad Of The Gliding Swan taken from Madhouse In Castle Street, a drama recorded in the BBC Studios and broadcast on 13 January.

Seven songs are included from a performance at New York’s Town Hall on 12 April 1963, effectively Dylan’s first major solo show. This disc closes with three unreleased songs in the form of a live take on Talking World War III Blues, one of Dylan’s talking narratives that so often draws out the humour in his songwriting as demonstrated by the audience reaction, and sublime alternate studio takes of the classic Masters Of War and Girl From The North Country.

Disc 6 takes us through from July to October 1963, again taking in home and studio sessions alongside performances at the Newport Folk Festival. Notable previously unreleased songs include Only A Pawn In Their Game and Blowin’ In The Wind from a Voter Registration Rally in Greenwood and home recordings of Liverpool Gal and West Memphis, again all in remarkably good quality. We then move into the early recording sessions for Dylan’s third album The Times They Are A-Changin’ which was eventually released on 10 February 1964. Among the unreleased takes are early versions of Boots Of Spanish Leather and One Too Many Mornings, the song which ignited my long standing journey with Dylan’s music back in 1976 when I first heard it performed on the Rolling Thunder Revue tour. We also get rollicking piano driven versions of Bob Dylan’s New Orleans Rag and Key To The Highway.

Discs 7 and 8 comprise the complete and unedited version of Dylan’s legendary concert at New York’s Carnegie Hall on 26 October 1963 which has all been released in some form or other but not in this fashion and maybe not with some of the song introductions……and not before time! From my perspective this is one of the most historically significant shows that Dylan performed in this period and probably his career, almost signifying the ‘arrival’ of Dylan. This is the sound of one man and his guitar transfixing an entire room like never before, and life for Dylan and indeed the world, would never be the same again.

Carnegie Hall is also probably my favourite representation of Dylan performing acoustically, with his wonderful song craft displaying the startling imagery that became such an outstanding feature of Dylan’s creativity. It’s a stunning recording with some beautiful arrangements all surrounded by the sense of nervous excitement that typified this period of Dylan’s live performances, not forgetting the humour that Dylan always brought to the fore, notably in his story leading up to singing Blowin’ In The Wind. For anyone wishing to enter the world of Dylan’s Bootleg Series, this complete show for me is worth the admission price on its own.

Through The Open Window is a fine chronological representation of Dylan’s embryonic years, charting his development both in the studio and on the live stage through that very early period in his life. It documents the shift from performing covers of so many songs which formed the very bones of the legacy that fuelled Dylan’s fire, right through to developing his own unique and masterful songwriting skills which filtered through into his own early releases, making such a marked and long lasting impact on what at that time was very much an unsuspecting world. Whilst the purist fans may still yearn for the release of more extensive archives which are known to exist, this at least is a collection which does meet that stated aim of connecting “the past and the present” and gives us a more cohesive and easily accessible source to celebrate the emergence of someone I consider to be the greatest songwriter of them all.

Of course what this release also achieves is a preservation of some of the lasting mystique that surrounds Dylan both as a songwriter and a human being, something that A Complete Unknown also does so admirably, although perhaps less obviously to the untrained eye in the way that it distorts some of the facts, events and characters involved in Dylan’s early life, albeit it under the watchful eye of the great man himself. The enigma of Bob Dylan lives on and thank goodness so does he, now 84 years young and heading for yet another visit to the UK in November. I cannot wait!

You can pre-order Through The Open Window in all its various forms here.

You can find Bob Dylan on Facebook, X (Twitter), Instagram and his website.

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All words by Ian Corbridge. You can find more of his writing at his author profile here.