Think you know Bob Dylan? A new box set offers revelations from his early career that will shock even the most diehard fans.
On a balmy, late-summer evening, the suits at Sony Legacy convened a group of journalists and Bob Dylan scholars at Electric Lady Studios, the subterranean recording studio Jimi Hendrix built in the heart of Greenwich Village shortly before his death, to unveil the eighteenth installment in Bob Dylan’s Bootleg Series.
With Sony now the sole stewards of Dylan’s recorded catalog, there were rumblings in Dylan fandom that The Bootleg Series Vol. 18: Through The Open Window, 1956-1963 might not meet the high standards of previous volumes. But with interest in Dylan’s early years at an all-time high—the result of the massive success of last year’s Timothée Chalamet-starring biopic, A Complete Unknown—those suits clearly knew the stakes were too high to drop the ball.
The result is an eight CD box set, out Oct. 31, chock full of both audio and historic revelations. As the renowned historian and author of the excellent Bob Dylan in America, Sean Wilentz, who wrote the absorbing essay included in Through The Open Window, and musician Josh Ritter, who led the evening’s proceedings, said over and over, it’s nothing short of astonishing that, after all his time in the spotlight, it’s still possible to encounter revelation after revelation in Dylan’s early evolution.
“I was thrilled to be able to experience this music through the lens you’ve created,” Ritter said to Wilentz during the preview of the set. “It enriched the whole period. It’s an astounding read. And then, to be able to listen to these songs for the first time and hear this sound coming across the plains, from the dark of night or the cold of winter, it was beautiful.”
Through The Open Window offers a more fully realized version of Dylan’s origin story than ever before, its 139 tracks acting as a soundtrack to guide anyone looking to discover what Dylan has to offer beyond A Complete Unknown.

The Daily Beast spoke with Wilentz, who first saw Dylan at his infamous concert at New York’s Philharmonic Hall in 1964, about some of the key revelations fans of all stripes will encounter when the box set, due this Friday, becomes available.
It took Dylan less than a year in New York City to completely transform his sound.
Wilentz: “It’s amazing how quickly he developed, first as a performer, then as a songwriter. Compare the ‘Madison Tapes’ here, which is more or less how he performed when he arrived in the Village in January 1961, to, say, the outtake of ‘Ramblin’ Round’ from November. In less than a year, he’s become a master interpreter. Then compare ‘Bear Mountain Picnic,’ from mid-1961 to ‘A Hard Rain’s A-Gonna Fall,’ when he was just 21, not much more than a year later. In a year and eight months, he’d gone from an enthusiastic, ordinary kid to a re-inventor of the folk tradition, with flashes of genius beyond even that. It’s hard to think of any other modern greats in any field moving that far, that fast.
Dylan was also “much closer to the civil rights movement and to its younger stalwarts than most people might think.”
Wilentz: “You get this in part from listening to the entire tape from the Greenwood SNCC rally on July 6, 1963, but I think this set both explodes the myth that he was a protest singer as well as Dylan’s claim that he wasn’t a protest singer. The Carnegie Hall version of ‘Masters of War,’ complete with Dylan’s searing introduction, is a perfect example. And one thing I think my essay gets into isn’t so much about myth-busting as to showing how close he was to the civil right movement.
‘Blowin’ in the Wind’ is the only song repeated on four different occasions in the box set. Thanks largely to Peter, Paul, and Mary, it became the signature song of his early career, and the one for which I imagine he’s still best known. It appears in different contexts to show something of its life as songs do take on lives of their own. But I’d single out the performance at the Student Nonviolent Coordinating Committee voting rights rally in Greenwood, Mississippi, with cops hanging around the edges, because it’s so moving and I think will be amazing for people to hear. Here is Dylan’s connection to the civil rights movement which, though never of the conventional political kind, was closer than most people realize.”

Dylan’s story was not “solitary” but rather relied heavily on “community.”
Wilentz: “The nurturing of his genius, the soaking up of genres, that’s a familiar story about Dylan. But to hear it this close-up, in so much detail, enriched my understanding of just what those words mean. So, I was especially happy to include the very informal recordings, most of them not known to the wider world. You hear him working on his own stuff, adapting works by the likes of the ’20s bluesman Richard (Rabbit) Brown (‘James Alley Blues’), spinning off lines that would recur in his work years, even decades, after, and learning not just what he once called his “lexicon in folk music and blues” but improving as a guitarist above all. By the time you get to the outtakes of, say, ‘Boots of Spanish Leather’ and ‘Seven Curses,’ he’s putting it all together.
In many ways, Dylan was and is an inquisitive scholar, who’s not satisfied until he knows exactly how something works. But another thing that came across was how the story was not a solitary one, but involved an entire community, the Greenwich Village folk community, plus its outcroppings in Minneapolis and elsewhere. Without that, Dylan’s story would have been very different, and might not have happened at all.”
Robert Johnson influenced Dylan almost as much as Woody Guthrie did.
Wilentz: One thing that stood out was his closeness with Black blues musicians, like John Lee Hooker, Big Joe Williams, Victoria Spivey, who found something special in him. That, plus just how strong an influence Robert Johnson was on his songwriting, as well as his phrasing and syntax after late 1961, was amazing to discover. I always knew how important Johnson’s influence was, but I’d now say he’s second only to Woody Guthrie as the influence on Dylan’s early years. He took those influences and soon was writing exceptional songs of an unexpected kind that seemed to come out of nowhere. So maybe I do have a favorite thing: That after all this time, and all of this listening, there are still things about Bob Dylan and his art that mystify me and knock me for a loop.”
The key tracks that showcase the “untold story” of Dylan’s first years as a New Yorker.
“Remember Me,” from February 1961, shows that Dylan’s taste ran well outside of folk music, let alone Woody Guthrie, when he hit the Village, with Dylan’s voice more of a croon than a grating Okie twang, unlike what most listeners will expect.
“Let Me Die In My Footsteps” from The Finjan in Montreal in 1962 is one of Dylan’s lesser known “protest” songs. This is a strong, live coffeehouse performance, which exemplifies Dylan’s approach to political matters. Dylan’s song affirms life. While plenty of people were writing songs about nuclear fallout, stressing the effects of nuclear testing, Strontium-90, destruction, Dylan decided to celebrate the land, the outdoors, outside the shelters. While others were learning to die, Dylan was learning to live.
“The Lonesome Death of Hattie Carroll” from Carnegie Hall in 1963, is, along with “Hard Rain,” the greatest song of his early career. But it’s sung here at the most important concert of his early career, for an audience that adored him, but had never heard this song before. You can hear Dylan’s stunning rapport with the audience, but also his own desire to put the song over, playing it slowly so that everyone could catch every word. A Dylan concert, then as now, always featured his very latest material, and here was a song he’d written just a few weeks earlier and that he knew was important, and so performs it with insistence.
Put these together and you can see the many layers of Dylan’s development.







