Bob Dylan - Through The Open Window (Album Review)

My personal journey listening to the music of Bob Dylan began about 34 years ago, and even back then, it took me a good year to develop a decent enough appreciation of his whole career to start making compilation cassettes of my favourite Dylan tracks. Also, only the first three-disc box set, Volume 1-3, of the Bootleg Series had been issued. So, with that, all the studio albums and the quite tasty ‘Biograph’ box set released in 1985, there were already a lot of style changes, distinct phases, and top songwriting to explore. Now, in 2025, I have a painstakingly compiled playlist found on Spotify called The Complete Chronological Bob Dylan that, just as the title claims, places every available track from each Dylan album, Bootleg Series, live albums, compilations and appearances on other artists’ records in exact order of known recording date, with everything else filed as accurately as possible. In total, to listen to the whole playlist uninterrupted from start to finish, it would take over 148 hours. No wonder that over the past couple of years, the word in Dylan chat circles has been that the Bootleg Series might be drawing to a close, with little left in the archive waiting for a repackage and release. I actually do not believe that to be the case; the Never Ending Tour alone could ensure that these volumes themselves have a touch of the infinite. However, there might come a day when the fundamentally essential titles in the series have all been issued. That being the case, then this, Through The Open Window: The Bootleg Series Vol 18: 1956-1963, will absolutely be one of the definitive, indispensable editions.

Through The Open Window opens with the very first recording Bob Dylan ever made. It was on Christmas Eve 1956 when the fifteen-year-old, as leader of his trio named The Jokers, cut a do-it-yourself 78rpm acetate with Bob bashing the piano and singing on a ramshackle but spirited cover of Let The Good Times Roll. What unfolds across the eight discs that follow is as thorough, exhaustively detailed and excavated a document of his early formative years as has ever been available. Played alongside the three original CBS albums from 1962 and 1963, there will be no richer audio experience of the period when Bob Dylan found his name, his unique approach and established an indelible place in the pantheon. These years have been permanently marked as the phase in which Bob started out as a Woody Guthrie derivative, evolving into the most potent writer of folk protest music the world over. The reason this particular release scores top marks is that it celebrates this era and its incredible music rather than, as on previous collections, setting their traditional acoustic stylings as something to be reacted against before the controversial explosion of Dylan’s so-called electric conversion.

Complete live concerts have been central to many of the Bootleg Series titles, and the entire show included on Through The Open Window, from 26th October 1963 at Carnegie Hall in New York, is up there with the greatest heard so far. It is the perfect conclusion to this period, and I would argue, a time capsule of the moment Dylan himself peaked within this chapter. By the time he recited material from these first three albums in 1965, as witnessed on film in Don’t Look Back, he was obviously a man whose muse had snaked off in a whole other direction. Here, however, on the back of a well-received second LP, Peter, Paul & Mary, taking his Blowin’ In The Wind to number one and fresh songs composed over the previous weeks for The Times They Are A-Changin’ album, including the title track, we capture a singer and writer wholly invested in this topical, socially aware music. Presenting classics like The Lonesome Death of Hattie Carroll to an audience unfamiliar with this new work, he enunciates so clearly and deliberately, ensuring that everyone follows the narrative. A lifetime away from the muted stage presence of Dylan today, here he tells a mocking anecdotal yarn and is sincere in his solidarity with the blacklisted Pete Seeger and The Weavers during a wordy introduction called Hootenanny Hoot. As detailed in the extravagantly illustrated 123-page accompanying book, Bob had a far greater, hands-on involvement with issues like civil rights that summer than is widely assumed these days. This concert recording shows us a singer committed to the words he sang; there is no irony or red herrings, the man had his teeth into something and was willing to articulate and lead—little wonder so many of his audience believed and were ready to follow.

Bob’s introduction to Masters of War that October night speaks volumes; he announces, “Some people said this song I wrote is very naïve, but I’ve got to stand here and really not care because I do actually hope that the masters of war die tomorrow”. This all begs the question, though, what changed? His next album, released in 1964, deliberately steered towards the personal and poetic; the seismic shifts that followed are well known. Less than one month after this concert, John F. Kennedy was assassinated. Bob’s devastated reaction is discussed in the book, and it is tempting to draw a connection between this and the urge to escape into the song-and-dance man jokingly alluded to later. Similarly, that desire to never be pinned down is another long-term Dylan trait that also alights throughout these tracks. There is a revealing exchange between producer John Hammond and Bob during the first album sessions, when John tries to get some information from the artist about Man of Constant Sorrow. He offers nothing but a disinterested “don’t know” to the question about who wrote it. Then Hammond persists, “Has anyone else recorded it?” Bob answers unhelpfully, “not that way.” “So, who has recorded it?” he pushes. “Judy Collins, but not that way.”

It is in these little archival jewels that the Through The Open Window box set becomes authoritatively essential. Album sessions are covered for all three of Bob’s official releases in the period, but it is the outtakes and studio try-outs, not the familiar versions, that are covered. There is an impossible amount of invaluable home recordings preserved with unexpectedly good audio quality. There are non-album songs recorded for Broadside Magazine not to be sniffed at; John Brown is, in fact, one of Bob’s strongest from the protest era. On top of that are radio and TV appearances, as well as more live sets, including genuinely rare tapes from Gerdes Folk City in April 1962 and Town Hall, NYC, one year later. There is an unexpected bounty in the shape of harmonica session work. Bob’s playing on a Carolyn Hester album has long been known and available to completists, but here, from those same sessions, we get to hear a scarce alternate take of I’ll Fly Away. Dylan’s harmonica turns up too on a Harry Belafonte recording of Leadbelly’s The Midnight Special from early 1962. We even get to hear a fly-on-the-wall moment as Belafonte acts as mediator, soothing producer Hugo Montenegro’s growing frustration with the young harmonica player’s difficulty nailing his part. And whilst John Hammond getting Bob to cut a band-backed single in late 1962 (going electric three years prematurely) is no longer a revelation, the attempted version of That’s All Right at those same sessions, with a more than passable Elvis styling to his vocal, is a discovery. It all adds up to a wonderfully deep, immersive and spectacularly constructed package dedicated to Bob Dylan’s early years. It should, barring some hard-to-see future uncovering like a complete recording of the January 1963 BBC play ‘Madhouse On Castle Street’ (represented here with one song excerpt), stand as the main artefact for a deep exploration of this period. For now, the Bootleg Series still has a lot to offer in its proper, meticulous and craftsman-like curation of an all-time legendary music figure.