In his 2004 memoir, Chronicles Vol. 1, Bob Dylan reflects on his initial venture to New York City, specifically Greenwich Village, in January 1961, having journeyed from Minnesota. At that time, Dylan was unfamiliar with the bustling city, but this soon changed as he became a pivotal figure within the Greenwich folk scene. This transformative phase in Dylan’s early career is the central theme of Through the Open Window, 1956-1963, the latest volume, the 18th, in The Bootleg Series, co-produced by Sean Wilentz and Steve Berkowitz.

The collection, spanning eight CDs with 139 tracks, includes 48 previously unheard recordings. It begins with Dylan’s take on “Let the Good Times Roll,” a track he recorded in a Minnesota music shop at the tender age of 15 in 1956, and concludes with his landmark performance at Carnegie Hall in October 1963. In between, the set offers a wealth of home and live performances, rare studio outtakes, and other gems. Iconic songs such as “Blowin’ in the Wind,” “A Hard Rain’s a-Gonna Fall,” “Boots of Spanish Leather,” “Don’t Think Twice, It’s All Right,” “Masters of War,” and “The Times They Are a-Changin’” are among the highlights.

Sean Wilentz, a respected history professor at Princeton University, contributed an insightful essay for Through the Open Window. He has also provided notes for earlier volumes in the Dylan Bootleg Series, including Live 1964 and The Cutting Edge, 1965-1966, and authored the 2010 book Bob Dylan in America. In a recent interview, edited for clarity and brevity, Wilentz delves into the musical brilliance of the collection and the pivotal role this era played in Dylan’s artistic evolution.

David Chiu: In your essay for Through the Open Window, you describe the collection as just a fragment of that era. Yet, to me, it feels like an expansive anthology of music.

Sean Wilentz: It really highlights the vastness of Dylan’s accomplishments. Though the collection spans from 1956 to 1963, much of it centers on 1961 to 1963. Our aim was to narrate the story of Dylan’s early development as both a performer and songwriter. Today, we recognize him as a Nobel Prize-winning songwriter, one of the few, but he had to start somewhere.

An esteemed professor of history at Princeton University, Wilentz also wrote a detailed essay for Through the Open Window (He also penned notes for the previous Dylan Bootleg Series releases Live 1964 and The Cutting Edge, 1965-1966, and wrote the 2010 book Bob Dylan in America. In this new interview — which has been edited for length and clarity — Wilentz discusses some of the musical highlights of the set and the significance of this period in Dylan’s growth as an artist.

David Chiu: You wrote in your essay for Through the Open Window: “Of that time and those places, this collection is just a fragment.” But to me, the box set is a massive compilation of music to absorb.

Sean Wilentz: It says something about the enormity or the size of what Dylan actually managed to get done. The set’s from ’56 to ’63, but much of it is really from ’61 to ’63. What we wanted to do was to tell a story of Bob Dylan’s early maturation as both a performer and a songwriter. We know him several decades later as a Nobel Prize-winning songwriter, one of the very few. But he had a beginning.

Dylan’s story is the story of a very particular genius flowering at a very particular time in a very particular place. That is to say, the early ’60s in Greenwich Village. And I think what Steve and I wanted to try and do was to present that story through music, through his performances, listening to him as he matures, as he finds his own voice, and then develops that voice.

Chiu: Were there some things that you discovered about Dylan that surprised you while working on this project with Steve?

Wilentz: His maturation as a performer before he becomes a songwriter. When he first gets to [New York], he’s already got a lot of talent. You can tell. He’s got many different voices. He’s very ambitious. He wants to do many different things, almost all at the same time.

By the time he’s cutting his first album [1962’s Bob Dylan], he had moved on from there. Nevertheless, you can hear him already maturing as a performer. He’s a different kind of performer. He is someone who can enter someone else’s song and make it his own in a way that you can hear it very early on. There’s a certain rock and roll attitude and all that. He’d begun as a rock and roller, and we make that clear, too. You can hear a bit of that, but by the time he gets to November 1961, when he’s cutting that record, he really knows how to get inside a song and make it his own.

There are a couple of examples of that in the box. The one that I like the most is the outtake of him actually singing “Ramblin’ Round,” which is a Woody Guthrie classic. And what he does with that song is really amazing because he sings it unlike anyone else has done it. He sings it with great feeling. It’s not even the best take of it, but it’s the one that we had. I find it very moving, and I think other people did too. When you read people discussing him, even this early on, there was something very special about him. It’s a kind of empathy, understanding what somebody else has done, but it’s also making it your own. And that’s what he manages to do.

He’s already been writing some songs of his own, and some of them are okay. Some of them are interesting. But by April ’62, he’s writing “Blown’ in the Wind,” which is a quantum leap beyond what he’d done before. And then by September that year, he’s writing “A Hard Rain’s a-Gonna Fall,” which is three quantum leaps beyond what he had done with “Blowin’ in the Wind.” So this is a young man in a hurry, but it’s also a young man who is learning a great deal, working very hard. I don’t think I was quite prepared to hear all of that going on and for it happening so rapidly.

Chiu: Are there a couple of tracks on this set that might be considered the Holy Grail for die-hard Dylan fans?

Wilentz: Well, the obvious one is “Liverpool Gal,” which he recorded in 1963. This is a song that he recorded while visiting his friends in Minneapolis, and it was recorded by his friend, Tony Glover, then known as Dave Glover, from the band Koerner, Ray & Glover. It’s a song that describes his trip to London in 1962-1963, which was a very important trip in itself. It’s unlike many of his other love songs written at the time in very interesting ways.

The ones that actually stand out for me may not be the ones that other people find most interesting. And those are the ones that he does in the private tapings with the McKenzies and the Baileys [“Ballad of Donald White” and “Ain’t No Grave,” respectively]. This is just him playing into a tape recorder, honing his craft, trying out new things. There’s one in particular that I found interesting, which is his recording of “House of the Rising Sun” in 1963, which is very unlike the version that he stole from Dave Van Ronk and ended up on his first record. It’s a much more raw, in some ways. I think it actually captures the song itself better than the original version because it is almost droning and raw and so forth. It shows Dylan to be endlessly inventive. I mean, here’s a song that he had recorded two years earlier, and he says to whoever is taping him, “This is the way I sing it now.” He sings it in a way that’s very powerful.

Chiu: Dylan’s arrival in New York City seemed like such perfect timing as the Greenwich Village folk music scene was booming. He sort of came in and gradually took over.

Wilentz: Well, timing is everything in life. There was a reason he showed up, which was that he wanted to see Woody Guthrie. But he was aware there was more going on.

Dylan did a lot to shape the Greenwich Village scene, but the Greenwich Village scene did a lot to shape him as well. Yes, he was there at the right time and he found the right people. Not everybody liked what he did at first, but he did have a coterie of very strong supporters. And he also found mentors like Dave Van Ronk and others who were able to introduce them to things that he might not have learned about any other way.

He hit an enormously vibrant place not just for folk music, but for all of the arts that were really focused on that little neighborhood in extraordinary ways. But then he made the most of it. So you have to give him a lot of credit for the timing because lots of people came there and they weren’t able to do what Bob Dylan did. It wasn’t just the music — there was dance, theater, comedy. It was all happening at the same time. He was so voracious in his appetite. All of it mattered to him, and you could hear a lot of it in all of his music as well.

Chiu: The set also includes Dylan’s live performances at civil rights events in 1963, including the March on Washington and the SNCC Voter Registration Rally in Greenwood, Mississippi.

Wilentz: Greenwood, Mississippi, was a dark and bloody ground for the civil rights movement. There had been a voting rights drive that the Student Nonviolent Coordinating Committee (SNCC) had gotten going a year before, but the repression was extraordinary. The threat of violence was constant just because they were trying to help Black people get to vote, which was something that Mississippi whites were resisting. And Greenwood was both a center of the movement, but it was also a center of the white resistance. So they were in collision.

Bob Dylan gets invited to go down there and be part of this freedom festival. This was not the [1963] Newport Festival. It was a much different kind of thing. It was a voting rights rally, but they wanted to bring some singers in to help. So they bring Dylan in, along with Pete Seeger and Theodore Bikel.

They ask him to sing Blowin’ in the Wind. But first, he wants to sing a song about Medgar Evers, [“Only a Pawn in Their Game”], which was an extraordinarily important song. So he sings this song. It’s not indicting the killer of Medgar Evers — it’s indicting the system that created the killer. And people got it. They applauded quite loudly. He also made a lot of close, good friends within the SNCC organization. His commitment was not simply political. It actually became personal and those friendships lasted. So all of that’s going on in this one little concert in a dusty little field outside of Greenwood, Mississippi. It’s an incredible moment.

Chiu: The set features his October, 26, 1963, concert at Carnegie Hall presented in its entirety. That performance was a crowning achievement for him at that point in his career.

Wilentz: Without a question, that’s the culmination of what he had been doing. Everything we heard from at least 1961 led to that concert. And it was an extraordinary event. He is performing songs that people had not yet heard, including “The Times They Are a-Changin’”. He saves “The Lonesome Death of Hattie Carroll” towards the end of the concert and really wants people to listen to it because he knows that it’s an important thing.

So the songwriting is there, but it’s also the event itself, and you can hear that on the record. We want to make sure that that was clear on the [box]. He is by now not only a popular performer, but he has now attained a kind of fame that was unprecedented, a kind of convergence of bohemian attitude and very upfront politics, and then this mass appeal that was going on. And you hear the young people there who are hanging on every note, cheering madly. By the time we get to the end of the concert, they are almost delirious.

It’s a very political moment. A lot of the songs are political. This is October 1963, the end of a year, especially in the history of the civil rights movement, which had been decisive. And his songs were in part about that. He sings “Only a Pawn in Their Game” at that concert. It’s all kind of coming together. You can hear it not only in his voice and not only in his command of the stage and of his material, but in the audience as well. And it’s the interaction between the audience and Dylan that I think helps make that [show] more than a musical event. It makes it a cultural event.

Chiu: What do you hope people – including the diehard Dylan fans and the casual listeners – will come away from Through the Open Window?

Wilentz: I just hope they enjoy the music. There’s a lot of music on here, and the music itself is meant to be enjoyed and played over again. What you’re going to see is the growth of a great artist in a community at a particular time, in a particular place. The other thing I hope they come away with is an understanding of the multivalent aspect of Dylan — not only his talent, but of his own listening and his own art.

People think of Bob Dylan as a kind of guy in a work shirt and blue jeans singing “Blowin’ in the Wind,” and with a kind of raspy voice. What you’re going to hear is a much more complicated character, artistically, personally, etc. You’re going to hear as many different voices. There’s the voice of him as a 15-year-old [on “Let the Good Times Roll”]. But there’s the voice of him singing a country western tune. “Remember Me,” which is an old country song done in 1940 by a pair called Lulu Belle and Scotty, “the Sweethearts of Country Music.” And he sings that song in a voice that’s practically crooning. He’s always had a lot of different voices in him, and he knows how to use them. You can hear that on this record as well. It’s the variability, the complexity, the eclecticism. Dylan’s interested in everything, and he’s going to use everything for his art. And then he’s going to perform it in ways that are much more variable than people have any idea about. So they’ll come away with that, too.

There’s a continuity to all of that that people will, I think, also get a sense of from this record if they listen to it hard enough. If you were to listen to the Carnegie Hall concert, and then listen to the concert of Philharmonic Hall in ’64, and then listen to anything he was doing after Newport in ’65, including the early rock concerts and so forth, you’ll see a guy changing enormously. But at the same time, there’s a continuity to it. What he does is he picks up something that he finds fascinating, interesting, magical, mystical in the songs. And then he enters it and makes it his own. That’s what he’s still doing in many ways.