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Bob Dylan met Columbia Records’ John Hammond on September 14, 1961 at the apartment of folksinger Richard Farina and his then-wife Carolyn Hester.  Dylan had been invited to Carolyn’s rehearsal session as a harmonica player.  Hammond later told the story of being so impressed with the young man from Hibbing, Minnesota that he decided to sign him on the spot.  A subsequent audition took place, and when Dylan – then dazzling audiences at Gerde’s Folk City on a bill shared with The Greenbriar Boys – showed up for Hester’s Columbia session on September 29, he was presented with a recording contract of his own. The rest is history.  The beginnings of Dylan’s enduring career have been revisited by Columbia and Legacy Recordings on Through the Open Window, the eighteenth installment of the artist’s long-running Bootleg Series, covering the period of 1956-1963.

The first Bootleg volume since 2023’s Fragments, an exploration of the 1996-1997 Time Out of Mind sessions, in, in some respects, not your typical installment of the series.  A handful of tracks have been reprised from the very first Bootleg Series collection, while a couple more turned up on Volume 9, The Witmark Demos.  Still other tracks were previously aired on the ultra-rare 50th anniversary “copyright collections” (intended to preserve copyright in Europe for material that otherwise would enter the public domain there).  But seeing as the copyright collections fetch high coin – an original edition of the 2012 set of four CD-Rs would currently set you back upwards of $2,300.00 per Discogs – a wide-release presentation was inevitable.  Though completists will still yearn for a commercial release of those sets in their entirety, Through the Open Window has the advantage of careful curation.  Unlike those “dumps,” this 8-CD collection has been fastidiously compiled by producers Sean Wilentz and Steve Berkowitz to tell a story in words, music, and text.

It’s the story of a young man prone to spinning tall tales even as he discovered his authentic self through music.  Through singing the songs of others – notably, but not exclusively, Woody Guthrie – the young man found his own voice and the idiosyncratic phrasing that’s set him apart for nearly 70 years.  Private recordings, live performances, studio outtakes, and demos tell this story, chronicling his vivacity and hunger as he effected the transition from Robert Zimmerman to Bob Dylan.

The primitive, early home recordings here nonetheless show a young singer in thrall to rock and roll and blues; the teen pop of “I Got a New Girl,” recorded in May 1959 at pal Ric Kangas’ Hibbing home is a particular delight.  But soon, spirituals and country join the expected folksongs to paint as full a picture of Dylan’s influences as has ever been captured on one collection.  The mélange of styles will be no surprise to anyone who read Dylan’s Chronicles Vol. 1 or listened to his Theme Time Radio Hour broadcasts, but there’s a thrill hearing the artist evolve from track to track, soaking up every song and style as he honed his craft.  (Thankfully Dylan’s friends were present with cumbersome recording equipment to preserve these recordings.)

Guthrie’s “Jesus Christ” (September 1960) and Scott Wiseman’s “Remember Me” (February 1961) are early highlights here, with the latter particularly pretty and heartfelt.  The box then traces Dylan to the fertile Greenwich Village folk scene, recently recreated in director James Mangold’s biopic A Complete Unknown.  There are selections from a Gaslight Café show of 1961 – a subsequent 1962 gig there was released on CD back in 2005 – as well as recordings from such now-legendary Village venues as Gerde’s Folk City and The Folklore Center.  A sense of community is prevalent in these recordings; the Gerde’s tracks feature influential musician and jugband leader Jim Kweskin.  Wilentz and Berkowitz have unearthed invaluable studio recordings, too, such as an alternate take of “I’ll Fly Away” from the pivotal Carolyn Hester session of September 29, 1961 at Columbia’s Studio A.

Five tracks from the sessions for Dylan’s self-titled Columbia debut welcome listeners back to Studio A, with the rehearsal of folk staple “Man of Constant Sorrow” among the most compelling cuts here.  Dylan sounds impossibly youthful, down to earth, and confident in the chatter following the rehearsal take, quipping about Judy Collins’ performance of the song.  Three additional takes recorded during the Bob Dylan sessions were included on the original Vols. 1-3 of the Bootleg Series: “House Carpenter”, “He Was a Friend of Mine,” and an original composition, “Man on the Street.”  (The last outtake is Woody Guthrie’s bright “Ramblin’ Blues,” also known as “Ramblin’ Round.”)

A clutch of recordings from a December 22, 1961 party at Bonnie Beecher’s Minneapolis home find Dylan’s skills as a storyteller coalescing.  His voice on these intimate recordings captures his blazing ambition and profound self-belief as well as his intensity (see the furious, possessed “Dink’s Song”).  His sense of humor is also evident as on his rap about East Orange, New Jersey (“Never go [there]…it’s a horrible town!”)

Dylan sang old favorites as if he was singing them for the first time, bringing the songs inward and anticipating the advent of the “singer-songwriter.”  On the Freewheelin’ Bob Dylan outtake of Hank Williams’ “Lonesome Whistle,” he’s recording in an Americana vein long before the term was coined.  His own increasingly prolific writing reflected a desire for his music to be “of the people” and not of the elite class; his introduction to a near-breathless “Talkin’ New York” from Gerdes Folk City in April, 1962 explicitly expresses this sentiment.

The Freewheelin’ sessions yield numerous treasures here, including a haunting “Rocks and Gravel” and vivid alternate take of “Mixed-Up Confusion” which would become Dylan’s first Columbia single.  (The released take has had a checkered history in the digital age, too, with the original mono single release still a rarity.)  The alternates of “Masters of War” and “Girl from the North Country” are, respectively, blistering and sweetly affecting.

“Let Me Die in My Footsteps” was one of four songs recorded for Freewheelin’ but not heard on the final LP; it was reinstated (along with “Rocks and Gravel,” “Rambling, Gambling Willie,” and “Talkin’ John Birch Paranoid Blues”) for a 2025 Record Store Day vinyl edition.  (Unfortunately, all of those final takes heard on that vinyl LP are not collated here.)  Dylan’s brutal lyrics to “Let Me Die” are sadly as truthful today as they were when he sang them in front of a Quebec audience in the 1962 recording preserved here.  Note the number of prominent political and civil rights figures whose appearances pepper this collection, from Harry Belafonte to Ossie Davis.  Though Dylan bristled at the description of “protest singer,” there’s no doubt he was at the center at the youth movement that led to so many significant changes in the 1960s.

The Canadian performance of “Let Me Die in My Footsteps” isn’t the only evidence of how quickly the Dylan legend was spreading; Through the Open Window also features a performance of “Ballad of the Gliding Swan” from the BBC’s London studios, recorded in January 1963.  His Town Hall performance of a few months later is another triumph, particularly the atmospheric reading of “Dusty Old Fairgrounds.”  His busy 1963 is also represented by Newport Folk Festival performances on which he’s joined by Joan Baez, Pete Seeger, and Peter, Paul, and Mary (the latter, of course, on “Blowin’ in the Wind” which they took to No. 2 on the Billboard Hot 100).  A voter registration rally found Seeger and singer-actor Theodore Bikel on hand.

Dylan’s third studio album, 1964’s The Times They Are A-Changin’, was his first to boast exclusively original compositions.  Selecting the final songs from Dylan’s rapidly growing backlog was no small feat, and Through the Open Window has numerous revealing outtakes such as the ballad “Seven Curses” (reprised from the first Bootleg set) and “Bob Dylan’s New Orleans Rag.”  With such songs as “Boots of Spanish Leather” and “The Lonesome Death of Hattie Carroll,” Dylan’s songwriting was maturing, arguably faster than any of his contemporaries.  Those songs and others here demonstrated a wizened sensibility that belied his young age.  An informal September ’63 California recording of The Times They Are A-Changin’s title track is rough-hewn but mesmerizing in its directness and perfect in its imperfection.  (He was back in Minnesota where more informal recordings were preserved, including his only performance of “Liverpool Gal.”)

Through the Open Window culminates with Dylan’s famous Carnegie Hall concert of October 26, 1963 on its final two discs.  The show has been newly mixed to further illuminate this true “a star is born” moment.  (A rare disappointment here is that the Town Hall show of earlier in the year wasn’t re-presented in its complete form, though it, too, has long circulated among fans.)  One can practically hear the electricity in the air as Dylan offers some of his most incendiary music including “A Hard Rain’s Gonna Fall,” “Talkin’ John Birch Paranoid Blues,” “Masters of War,” and “The Lonesome Death of Hattie Carroll” with an immediacy and a power that’s undeniable.

Mike Piacentini and Steve Addabbo have beautifully mastered the material from a wide variety of sources, making the sound as uniform as possible given the disparate original sources.  As with all previous Bootleg Series volumes, the accompanying text is essential to fully appreciating the audio contents.  The 124-page hardcover by Sean Wilentz is loaded with rare photos, advertisements, newspaper clippings, and memorabilia images that draw the listener in even closer to Dylan’s early days.  A second hardcover book within the slipcase holds the six CDs in slots.  Each disc is adorned with a Columbia replica label in a different color while the pages holding the discs recreate original tape boxes.

For fans who already have (almost) everything on bootlegs and copyright collections, The Bootleg Series Vol. 18 still offers one distinct advantage: that of curation.  For those who haven’t yet taken a deep dive into these formative years for Bob Dylan, the set is one-stop shopping with a comprehensive selection of the most significant material.  It’s a testament to Bob Dylan’s artistry that we’re still discussing these early recordings over 60 years later even as the man himself is still on the road with his so-called “never ending tour,” packing houses with a setlist that still surprises.  This Open Window onto a bygone era – one that still informs the social and political upheaval today – is one that’s well worth a look.

The Bootleg Series Vol. 18: Through the Open Window is available in various formats.  As an Amazon affiliate, we earn from qualifying purchases.

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