In 1956, Robert Zimmerman was a 15-year-old kid, a misfit in his small Midwestern town, and leader of a ragtag rock’n’roll combo who compensated for their lack of technique with boundless enthusiasm. In 1963, Bob Dylan was arguably the most celebrated pop artist in America, whose songs were hailed as standards before he could even record them and whose fans considered him to be a living, breathing manifestation of the American folk impulse. That kid wailing on his band’s cover of Shirley & Lee’s “Let the Good Times Roll” back in St. Paul, Minnesota, could never have predicted where he’d end up in seven years (he’d not even heard of Odetta or Woody Guthrie yet), and the conquering hero closing out his first sold-out Carnegie Hall performance with a spirited and weirdly prophetic “When the Ship Comes In” had already tried to erase his old self from his biography. He claimed to friends and interviewers and colleagues and onlookers that he was born and raised in New Mexico, ran off with the circus, toured with Conway Twitty, and any other fabulation that crossed his mind, so perhaps he thought those two versions of himself were incompatible. But there was always something of the rocker in the folkie and a bit of the folkie in the rocker.

Through the Open Window, the 18th installment of Dylan’s never-ending reissue series, connects these two figures intimately, tracing the artist’s seven-year rise across 8 CDs, 165 tracks, and nearly nine hours. It’s not the largest Bootleg entry; the collector’s edition of The Cutting Edge beats all comers with 18 CDs, while Trouble No More sprawls to as many as 10 CDs. (You want that much mid-’60s electric Dylan, but who besides the most committed Bobophile needs that much born-again Dylan?) Regardless, nothing in the series has the same scope of this new set. Most Bootleg installments drop you into a pivotal moment in Dylan’s life, a meaningful year or two, but Through the Open Window covers almost a decade during which he made great strides. It plays less like a box set and more like the audiobook of a Great American Novel: a travelogue from the Midwest to Greenwich Village and a coming-of-age story of an artist hitting young adulthood amid the dreamers and schemers of New York City. It follows Dylan as he hangs out in shabby Manhattan apartments, as he lingers over coffee at Café Wha?, and as he tries out new songs and routines and personae onstage. It follows him into tiny Cue Recording Studio and historic Columbia Studio A, to a poorly attended show at the tiny Carnegie Chapter Hall, and finally to his climactic sold-out show at Carnegie Hall.

Here’s a box set where the length is not only justified but an essential part of the experience. It’s made for total immersion; whether you’re a committed obsessive or merely curious, it’s meant to be lived with for a few weeks, part of your daily routine for a while, exactly like a good book. You won’t get that experience with the 2xCD highlights edition or even the 4xLP set, which are really just the CliffsNotes versions. So start with the first track and listen for a while. Mark your place and start again later. Ignore other people to keep listening. Imagine those apartments with their thin curtains and bare mattresses on the floor, those clubs with their cigarette smoke and lines of hopefuls waiting for their few minutes on a small stage, those studios with their pristine acoustic tiles and engineers in suits and ties. Listen as Bobby Zimmerman becomes Bob Dylan.

You couldn’t write an opening chapter better than pimply Bobby leading his fellow teenagers through “Let the Good Times Roll.” The lo-est of fi, it is barely legible, and there is honestly nothing noteworthy in the performance beyond who is performing. It’s exactly the kind of track, however, that works well in the context of a sprawling box set, partly because it’s very short (37 seconds) and mostly because it so perfectly sets Zimmerman up as a nobody who becomes somebody. How many teenagers were obsessed with rock’n’roll in 1956? This kid was only one of a couple million. Later, you can hear the moment he learns about folk music and when he begins his defining obsession with Woody Guthrie: The guitars switch from electric to acoustic, there is more strain and gravity in his performances, the sound of someone trying to live up to the songs he’s singing. This is when he breaks free of those millions of kids and becomes one of thousands besotted by folk. Where they might have seen the music’s history as something that would automatically justify their presence on any stage, Dylan saw that and much more.

These are not lost years in Dylan’s life; in fact, they are among the most documented in his biography, thanks to Bootleg Series Vol. 9: The Witmark Demos: 1962-1964, Martin Scorsese’s No Direction Home, James Mangold’s A Complete Unknown, and even Dylan’s own Chronicles Volume One. It’s not the most glamorous era, lacking the prickly rebellion of going electric and the gleeful rowdiness of The Basement Tapes, nor is Dylan the most sympathetic of protagonists. His penchant for self-fictionalization during this period is notorious and at times obnoxious—he insisted on the three Ns in his early stage name, Elston Gunnn—but less well known is his wide-eyed wonder, his gawky attention-seeking. This is the guy who carried around The New York Times with Robert Shelton’s article about him, which Dylan would read aloud to anyone within earshot. There’s a bit of boastful self-regard there, but also a kind of dumbfounded amazement that he actually exists to other people.

Inside of a song, he’s an even wilier character, and Through the Open Window reveals an artist trying to find his voice and then convincing others to listen to it. At first he sounds most purposeful when he’s playing with other people, such as Danny Kalb, a slightly more experienced musician who adds sharp guitar runs to “East Virginia Blues” and “K.C. Moan.” Even as a session player, he sounds like a perfectionist, always absorbing new tricks and techniques. More telling than his harmonica playing on Harry Belafonte’s 1962 cover of Lead Belly’s “The Midnight Special” is the tense exchange with producer Hugo Montenegro over a riff Dylan was asked to play on the intro. Belafonte, chill as ever, tells the kid to take his time. He tried so many different things during this era, even working with a jazz combo for a flop single (although their cover of “That’s All Right Mama” sounds like a test run for his thin-wild-mercury sound just a few years later). While very few of them stuck, you can hear him learning as he goes.

As he hones his picking and strumming, Dylan gains confidence as a vocalist who knows when to howl or bleat or holler or croon or hang back and be quiet. The sheer force of his voice is no real revelation, but this compilation explores his developing technique in greater depth than any other Dylan set even attempts. Listen to his stark versions of Guthrie’s “Pastures of Plenty” and the country song “Remember Me,” both recorded at a friend’s home, and marvel at how he seems to be editing his vocals and guitar playing, removing every note but the most essential. Or cue up the various versions of “Blowin’ in the Wind,” regarded as his first masterpiece and a hit for Peter, Paul & Mary before he’d even released his own version, and hear how he lets the song be a little slippery, how he revels in what Sean Wilentz in his lengthy liner notes calls its “ambiguous indeterminacy.” Dylan always pushed against his reputation as a protest singer, despite writing some of the greatest protest songs of the rock era, and he sings this song like he’s trying to figure it out himself, finally realizing that it means something completely different depending on who’s singing it and in what context. Through the Open Window includes that and other songs from his first appearance at the Newport Folk Festival in 1963, back when he wouldn’t dare plug in. If he had divided feelings about the venue and his role there, it doesn’t come across in his performance, especially when he leads a choir of contemporaries—Joan Baez, Peter, Paul & Mary, the Freedom Singers, and others—in a rousing sing-along. They all sing “Blowin’ in the Wind” with a sense of destiny, as though they are making a new world just by singing this song together.

In one of the finest moments of sequencing on this set, the next song up is “Boots of Spanish Leather,” an outtake from the Freewheelin’ sessions with Tom Wilson (Dylan would eventually re-record it for The Times They Are A-Changin’ in 1964). The contrast between the rousing chorus of “Blowin’ in the Wind” and the stillness of “Boots” is jarring enough to bring out new aspects of each song, with “Boots” sounding even lonelier, even more despairing. Written during a trip to Italy as his relationship with Suze Rotolo appeared to be crumbling, it sounds intimate and unguarded, intensely private rather than public; he needs a quiet moment to himself in order to rouse an audience with his friends.

Though known in folk circles, Dylan was still struggling to find a larger audience and break through to the pop market. He signed with Columbia in late 1961, which is roughly where Act II begins. He recorded his self-titled debut with John Hammond producing, but it was not the breakout anyone expected. Here’s where you might want to place your bookmark and give that album another listen, just to get a feel for how this young man presented himself to the world; unexpectedly, Bob Dylan might work better as an addendum to this bulky novel than as a standalone release. Even Dylan considered it a failure, both commercially and creatively, and he was moving so fast that these traditional tunes and talking blues were old news by the time it was released.

His follow-up, The Freewheelin’ Bob Dylan, did not come easy. He worked through a series of aimless sessions over several months, finally piecemealing an album that wasn’t too dissimilar from his debut. At the last minute Columbia decided that “Talkin’ John Birch Society Paranoid Blues” was potentially libelous and removed it from the album. Dylan was irate, but it worked out in his favor, as it gave him a chance to quickly record several new songs and redo about half the album, including “Girl from the North Country” and “Masters of War”—two of his best compositions from the era. The new tracklist sharpened his Cold War fears while also introducing more intimate struggles, in particular his insecurities about Rotolo. The album toggles gracefully between the public and the private, each lending weight to the other, which contributes to its status as Dylan’s breakthrough as well as just one of the best folk albums ever made.

Through the Open Window could end there, with Freewheelin’ hailed as a masterpiece that sealed his reputation with the folkies while bringing folk music to a larger audience. But that album is merely the set-up for the set’s cinematic climax at Carnegie Hall, which takes up the last two discs. The crowd sounds rowdier than expected, bringing their basket-house manners to this grander venue and seemingly cutting short his introduction to “A Hard Rain’s Gonna Fall” with their applause. He brings so many different Dylans to the stage: the outraged protest singer (“The Times They Are A-Changin’”), the lovelorn poet (“Boots of Spanish Leather”), the talkin’ bluesman (“Talkin’ World War III Blues”), the guy scared of nuclear annihilation (“Masters of War”), and the artist who’s over it all (a rambling story about the film Hootenanny Hoot and the commercialization of the folk movement).

This Bootleg installment ends with Dylan triumphant, hailed as a hero and a new kind of pop star: not merely an entertainer but an artist. Of course, it wouldn’t be long before many of his applauding fans were jeering at him, calling him a traitor for plugging in and writing such inscrutable lyrics. Through the Open Window gestures toward the rest of the story, toward everything that has happened in the past 62 years. Dylan has always had a strained relationship with this early material, especially those topical songs, and sometimes he kicks against them and sometimes he embraces their possibilities. During these seven years Robert Zimmerman discovered he could be Bob Dylan and Bob Dylan discovered he could be just about anybody. Anything was possible and nothing was certain, and this might be the only time in his life when that was true.