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Bob Dylan Scholarship Comes in ‘Through the Open Window’ » PopMatters

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Through the Open Window: The Bootleg Series Vol. 18 1956-1963

Bob Dylan

Columbia / Legacy

31 October 2025

The best releases in Bob Dylan’s Bootleg Series have focused on a particular album or tour. They’ve gone in-depth, but they’ve stayed narrow. The latest collection, Through the Open Window: The Bootleg Series Vol. 18 1956-1963, takes a different approach. This 18-volume set covers the first seven years or so of Dylan‘s music (from high school to his famous 1963 Carnegie Hall show) without falling into traditional pitfalls.

Too many archival releases mash together middling (or slightly different) outtakes and a few live cuts. Through the Open Window does something more ambitious, taking an essentially narrative approach to do two simultaneous tasks: explore Dylan’s early development as an artist and capture the essence of a scene. It does so with remarkable skill.

The set opens with the earliest Dylan recording, a messy, half-minute version of “Let the Good Times Roll” he recorded in St. Paul, Minnesota, with the Jokers. The kids have spirit, but there’s little to suggest they’ll do anything more than play around the house for a while. As the first disc progresses, it reveals Dylan’s quick growth, his early attempts at songwriting, and his discovery of Woody Guthrie‘s music. He sounds fine, but as he heads east on his way to New York City, there are only brief flashes of something more than an average folkie in his playing.

Bob Dylan’s 1963 Performance at Carnegie Hall (Through The Open Window: The Bootleg Series Vol. 18)

Everything picks up with his arrival in Greenwich Village. His sound begins to expand slowly, and his personality starts to come through in compositions like “Song to Woody” and the eternally odd “Talkin’ Bear Mountain Picnic Massacre Blues”. Dylan sounds more assured as he tackles traditional folk and blues numbers. He also meets Suze Rotolo, with whom he begins a relationship, and who would have a significant influence on his life for some time. He meets everyone around him now (Dave Van Ronk would prove particularly relevant to Dylan’s direction), making connections and playing whenever and wherever he can.

Suddenly, Dylan is recording his first album, a self-titled record that only includes two original numbers. What’s more interesting than the outtakes from that release is the music Dylan’s playing for fun, especially the home recordings made on a visit back to Minnesota. When he was last there, he was an indistinct folk singer; now he plays with confidence, and his charisma comes through. The latter part of disc two provides an enjoyable and enlightening look at Dylan playing loose and gaining comfort.

He makes yet another jump coming into disc three, which sees Dylan in a whole new mode, just a year or more after he arrives in New York. Politics come into his songwriting, but he quickly finds a way to write topical music that sounds more timeless than typical protest songs. “Blowin’ in the Wind” becomes an era-defining song even as the era begins. He also continues to explore the personal, but while he’s writing, he also begins work as a studio musician. His recordings with Harry Belafonte are delightful. An image of the era begins to cohere, the mix of artists and styles, of grinding anonymity and celebrity next to each other.

Bob Dylan, who seems to have only just mastered stumbling through Woody Guthrie songs, begins putting together a landmark album, The Freewheelin’ Bob Dylan. The following few discs in the set are a whirlwind, with Dylan playing here and there and recording multiple albums with different colleagues. The liner notes are essential for appreciating all that’s going on, and historian Sean Wilentz does an exceptional job (the notes would be worth the read as a standalone text). Dylan puts together not one but two albums and begins to play a series of significant events, and the recordings show the energy and breadth of his work. The stellar curation of this set makes it effective for both listening and academic research.

Disc six highlights those significant events — like the Newport Folk Festival and the March on Washington — as well as his burgeoning relationship with Joan Baez. By now, Dylan has already made a meteoric ascent, and every performance has a certain amount of star power in it. It warrants a return to the first disc and those early recordings, an ear open to possibilities that would have been unnoticed in the 1950s.

His growing stature and artistry earned him a Carnegie Hall concert on 26 October 1963. In less than three years, Dylan has conquered New York, and he opens with a strong version of “The Times They Are A-Changin’”. The audience sounds enthralled, responding in advance even to music that hasn’t been released yet. Dylan, forceful in performance, is relaxed and funny between songs. Only a small portion of this show has been released before, and it deserves this full presentation, with Dylan performing at the peak of his early era. It ends with “When the Ship Comes In” and a final harmonica blow. The song serves as a finale for both the show and the set, a declaration of a new era at hand.

Across eight discs, Through the Open Window covers all of Dylan’s first era, from childhood through his rise to Carnegie Hall. The era has been covered in different ways before, but maybe none as well as this. With so much archival material now available (and Dylan so well covered in music, books, and film), it’s almost surprising that there’s still such valuable work left. Still, in shaping this set, the producers have developed a collection that works on multiple levels (including being simply fun) while adding significantly to Dylan scholarship.

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Justin Cober-Lake

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