By the end of 1961, barely a year after arriving in New York City from the Midwest, Bob Dylan had already demonstrated a variety of facets. The proof of this can be found right at the start of “Through The Open Window,” the 18th installment of Dylan’s ongoing Bootleg Series.
That fall, Dylan, then just 20, recorded his first album with producer John Hammond. Among the many unreleased recordings found on the box’s eight CDs are leftovers from these sessions, including an alternate version of the traditional song “Man of Constant Sorrow.”
Dylan sounds like an insecure boy scout who seeks approval from his scout leader after tying a square knot. He does a take and then asks Hammond, “Did you record that?…Did you like it?” However, when Hammond asks if anyone else has recorded the song, a different side of Dylan emerges. “Not in this way… In a different way, I guess,” he says, before mentioning a colleague in the scene who had already released a version of the song. “Judy Collins did it. But not one version… not like that. This is another.”
A casual, revealing moment
On a compilation that gives us plenty of insight into Dylan’s development and creative process before his switch to electric guitar, this moment is both incidental and revealing. Dylan’s version of “Man of Constant Sorrow” isn’t significantly better than any other performer’s; he doesn’t rock them like other folk and blues songs he played at the time.
But his subtle rebuff to Collins is a sign of the cocky and brash boy already in evidence – the same one who could cut people down to size while redefining himself and shaking up both the New York folk scene and the world of pop in general.
From the Midwest to Greenwich Village
Through The Open Window covers the years 1956 to 1963 and serves as an unofficial companion to last year’s biography A Complete Unknown. It begins before the start of this believable and moving film, with a youthful Robert Zimmerman performing the Shirley & Lee hit “Let the Good Times Roll” – Dylan’s first known recording – in a music store in St. Paul.
The box set ends about two years before Dylan’s stormy performance at the 1965 Newport Folk Festival. Like the film, the box set tells a familiar story: an earnest and ambitious but seemingly awkward boy with a mysterious past moves to the big city, ingratiates himself with the music scene, impresses everyone with his skills and songs, and then leaves those inspired by headlines behind to move on to more ambitious, poetic and personal themes.
Another side of transformation
Of course, this story was also told in his official releases of the period – from Bob Dylan to “Another Side Of Bob Dylan” to “Bringing It All Back Home” and beyond. But “Through the Open Window” shows us another side of this transformation.
Using a wealth of sources – unearthed club recordings, private home tapes, outtakes, stage remarks – we follow Dylan’s move from the Midwest to New York, conquering the Village coffeehouse and club scene, trying out songs in front of friends, interacting with other artists, plundering parts of their repertoire (particularly his own). mentor Dave Van Ronk) and even interacted with an exuberant radio DJ.
As familiar as this development may be, we have never been presented with such a detailed document of this metamorphosis, showing how rapid, relentless and often breathtaking it was.
Rarities with historical value
Compiled by Steve Berkowitz and Sean Wilentz, the box set also includes material previously featured on previous editions of the Bootleg Series. But 48 of the titles were previously only known to collectors, which further increases their historical value.
We can finally hear one of his performances from the fall of 1961 at Gerde’s Folk City – not the legendary evening that got him his record deal, but one a few nights later. We hear the very first live performance of “Blowin’ in the Wind,” which shows how mature the song was even back then.
Not all of the rarities meet the high expectations: the set from Folk City is a bit unimpressive, and “Talkin’ John Birch Paranoid Blues” seems slightly over-the-top. But their inclusion in a Dylan collection is long overdue.
Over time, Dylan’s transformation from lively, bold folk newcomer to master of his craft can be heard in details large and small. Recordings of him playing songs by Woody Guthrie and Jesse Fuller before he moved to New York show how deeply he was already interested in American folk music.
We hear early versions of “Tomorrow Is a Long Time” or “Bob Dylan’s New Orleans Rag,” and even a song called “I Got a New Girl,” which suggests that Dylan was never a purist.
The joke of young Dylan
As anyone who saw his early performances in New York will testify, Dylan was funny. On these recordings he enchants the audience with absurd stories, ironic observations and his typical mischief. It’s a talkative, endearing side that was rarely heard later.
The box ends with the complete recording of his concert at Carnegie Hall in the fall of 1963 – a highlight that cemented his status. Here Dylan’s feel for traditional songs deepens, and his rapid development as a songwriter remains astonishing.
“Tomorrow Is a Long Time” becomes a dark, beautiful song; “The Lonesome Death of Hattie Carroll,” recorded at a friend’s home in Los Angeles, is fascinating. When Dylan steps onto the Carnegie Hall stage with three albums under his belt, he has completely found his voice, his songs and his presence.
This tape, which makes up the last two CDs in the box set, is unexpectedly revealing. The audience is silent during the protest songs, laughing at Dylan’s irony and appearing awestruck. It’s hard to imagine that he would soon abandon this approach – but Through the Open Window shows exactly that: Dylan was always on the verge of closing one window and opening another to a whole new world.

