Bob Dylan. The Bootleg Series Vol. 18: Through the Open Window 1956–1963. 8CD, Columbia Records and Legacy Recordings, 31 Oct. 2025.
Review by Gayle Wald, The George Washington University
Through the open window the voice of the beauty of the world came murmuring, too softly to hear exactly what it said—but what mattered if the meaning were plain?
— Virginia Woolf, To the Lighthouse
The 18th volume of The Bootleg Series is titled Through the Open Window, a phrase with mythological overtones. In Joseph Campbell’s typology of the Hero’s Journey, the open window is the Call to Adventure. The Hero may initially resist the Call, but its lure is strong. Leaving home, the Hero encounters obstacles as well as helpers. He is tested. But because he is the Hero, these tests will plant the seeds of his transformation. He will emerge from the tests with new knowledge, ready to take on new adventures.
The cover of the boxed set, released on October 31, gives visual form to the myth. It pictures Dylan on a New York City rooftop. The buildings behind him appear puny, reaching no further than Dylan’s knees. He gazes slightly upward, looking beyond the camera’s frame. His fingers are in his jeans pockets. His stance is a wide and grounded “V.”[1]
The hero’s narrative is borne out over the eight CDs that comprise the Deluxe Edition of this latest boxed set. (The streaming and LP versions are leaner, featuring “highlights.”) It begins in 1956, in a recording booth in St. Paul, Minnesota, as Bobby Zimmerman and friends tromp through a ragged but enthusiastic version of “Let the Good Times Roll,” a Shirley & Lee song then in high rotation on Black radio programs. It travels with Dylan to the college towns of Minneapolis and Madison, Wisconsin, where he first discovered folk music via Odetta and then Woody Guthrie; to the small and agreeably grungy Greenwich Village clubs where he honed his skills before a live audience; and to venues like Riverside Church and Town Hall, where he established his performing bona fides. It takes us into the studio with producers John Hammond and Tom Wilson as he records Bob Dylan and The Freewheelin’ Bob Dylan. And it culminates with a complete recording of Dylan’s career-defining October 1963 concert at Carnegie Hall, the nation’s most prestigious stage.
As this itinerary suggests, Through the Open Window is best approached as a document of the alchemy of painstaking labor, furious determination, and creative inspiration that is the condition of possibility of every artistic breakthrough. At no point in Dylan’s journey is his success guaranteed or inevitable. Indeed, I came away from my listening with a powerful sense of the work behind the creation of “Bob Dylan.” Cumulatively, the dozens of tracks that record his efforts circa 1959-1962—to teach himself dozens of songs, refine his picking and harmonica skills, experiment with vocal stylizations, and sharpen his abilities as an interpreter of songs born in times and places beyond his own lived experience—provide a useful context for the emergence of Dylan as a composer. They bring to mind Patti Smith’s notion of the musician as worker, reminding us that even familiar and beloved songs were made, not plucked from the ether.[2]
Yet although the tracks on Through the Open Window are the achievements of a particular person, at a particular time and place, in some quarters the boxed set has been received with a Robert-Johnson-at-the-Crossroads zeal. Reviews published less than 36 hours after the boxed set dropped reprise some of the very language that gave Dylan so much indigestion in the mid-1960s. (That said, they are dutifully reproduced on the Bob Dylan website.) MOJO referred to “Dylan’s miraculous New York transformation” and breathlessly declared, “every damn song is a transcendence.” Uncut described the boxed set as a document of “the dawn of a legend.”[3]
Perhaps it is inevitable that Through the Open Window will only solidify the “genius” narrative that has long trailed Dylan.[4] Words like “miraculous” and “transcendent” express admiration, of course, but they are also deeply ahistorical, running contrary to the evidence of the boxed set itself. This air of romantic inevitability also hangs over A Complete Unknown, the 2024 biopic that covers much of the same period as Through the Open Window, and might be seen as its companion piece (in terms of content as well as marketing). But while James Mangold’s movie culminates in Dylan’s electric set at the 1965 Newport Folk Festival, the new boxed set, by culminating at Carnegie Hall in October 1963, shifts the frame. The difference is telling. In A Complete Unknown, the Hero’s journey culminates in his need to symbolically slay his father (Pete Seeger) and rid himself of straightjacketing emotional encumbrances (Joan Baez, Suze Rotolo) so that he may become the Voice of a Generation. The result is an at times compelling but strangely depoliticized depiction of the folk revival. In Through the Open Window, in contrast, the Hero’s journey ends on a heady note of arrival. At the 1963 Carnegie Hall concert, unlike at Newport in 1965, Dylan is thoroughly enjoying himself, basking in the glow of artistic validation, of which fame is one measure. It would still be a while before the glow turned into a conflagration.
After the period of 1964-65, the years chronicled in Through the Open Window are the most studied of Bob Dylan’s career, covered exhaustively in work since Toby Thompson’s 1969 Village Voice series on Dylan’s “Main Street” origins and Anthony Scaduto’s Bob Dylan: An Intimate Biography. Most of the tracks it collects have circulated for years: on tapes traded among collectors; via social media (the complete April 1963 Town Hall concert, posted to YouTube before it was embargoed for copyright violation); and in earlier anthologies, including The Bootleg Series Vol. 1-3: Rare and Unreleased 1961-1991 (1991); Live at Carnegie Hall 1963 (2005); and The Bootleg Series Vol. 9: The Witmark Demos: 1962-1964 (2010). But as Sean Wilentz points out in the boxed set’s novella-length liner notes, it “differs from other renditions because it tells the story entirely through recordings.” The visual abundance of the boxed set—with its dozens of images of Dylan and reproductions of material artifacts including handbills, lyric sheets, posters, and recording-studio ephemera—somewhat belies this notion of sonic storytelling. But Wilentz is of course correct. Through the Open Window constitutes an unparalleled sonic chronicle of Dylan’s early musical formation, up to and including its “completion” at Carnegie Hall.
To listen to Through the Open Window track-by-track is not necessarily to have a linear experience, however. The quality and appeal of its tracks vary widely, with some—for example, unused studio takes from sessions for Bob Dylan (1962) and The Freewheelin’ Bob Dylan (1963)—being of interest primarily because they represent the road not taken. Home tapes—including from the living rooms of friends including Bob and Sid Gleason, Mel and Lillian Bailey, and Mac and Eve McKenzie—lack the energy of live concert recordings, in which we hear Dylan figuring out ways to put over his songs for strangers. On the other hand, such tapes give us insight into Dylan’s artistry at the moment in late 1961 when New York Times journalist Robert Shelton first extolled Dylan as “bright new face” and allow us the pleasure of observing Dylan trying out material in intimate settings.[5] Although his development as a guitar player and singer is most apparent, Through the Open Window attests to Dylan’s distinction as a harmonica player within the New York folk scene, and reminds us that his earliest recording work was as a harmonica accompanist for Carolyn Hester, Harry Belafonte, and Big Joe Williams and Victoria Spivey.
There is texture and detail in recordings that were never intended for public consumption. Among these, tracks with fly-on-the-wall snippets of conversation are some of the most interesting moments on the boxed set. We hear Belafonte suavely advising the 21-year-old Dylan to “Take your time, baby” as Dylan fumbles with his harmonica during a February 1962 recording session for Belafonte’s Midnight Special. (Did this make Dylan more or less nervous, I wonder.) Elsewhere, we eavesdrop on an impromptu November 1961 conversation in the Columbia Records studio between Dylan and producer John Hammond, after Dylan has played him an assured interpretation of the Kentucky folk ballad “Man of Constant Sorrow.” Written out, it reads almost like the script of a play, in which the dialogue hints at unstated but palpable feeling:
Hammond (nonchalantly): What was the name of that, Bob?
Dylan (echoing the nonchalance): “Man of Constant Sorrow.” Did you get that?
H: I did.
D (more hopefully): Oh, did you like that one?
H (understated): Sure, it’s all right. Who wrote that?
D: (deflecting) Uh, I don’t know. I don’t know who wrote that.
H: Has it been recorded?
D: Uh, not that way.
H: How has it been recorded?
D: Uh, a different way I guess.
H: Who did it?
D (more insistently): Judy Collins did it, but not a version like that. That’s a different one. Judy Collins on Elektra.
H (thinking ahead): Elektra. We’ll find out from Elektra who wrote the damn thing.
Columbia Records did “find out,” of course, slotting “Man of Constant Sorrow” on the A side of Bob Dylan. But what fascinates is the window this dialogue offers into the delicate relationship of producer and artist. The conversation surfaces untold emotional depths, as Hammond, clearly interested in Dylan’s performance, keeps his enthusiasm in check, while Dylan, even as he solicits Hammond’s approval, displays total confidence in his work.
While such outtakes place listeners in the recording studio, the live concert performance tracks on Through the Open Window give us a seat at some of Dylan’s earliest club appearances. We hear Dylan introducing his first public performance of “Blowin’ in the Wind” for a small Gerde’s Folk City audience on April 16, 1962. “It ain’t a protest song, or anything like that, cause I don’t write protest songs,” he protests, in an uncanny anticipation of the song’s reception. “I wrote this song …. I didn’t actually write it. I just sort of recorded it,” he explains, acknowledging the composition’s indebtedness to the spiritual “No More Auction Block” while echoing contemporary accounts of the feverish pace of his songwriting, including Joan Baez’s recollection of him “turning out songs like ticker-tape.”[6]
Other tracks afford us insight into Dylan’s earliest audiences. Hearing the patrons of the Gaslight Café join Dylan in singing the title phrase to “A Hard Rain’s A-Gonna Fall” in October 1962, just a month after he debuted it at a Carnegie Hall hootenanny, we understand how passionately they embraced the song and its challenging lyrics. I was particularly interested in hearing Gerde’s Folk City patrons react to an April 1962 performance of “Talkin’ New York”—not the G-rated version that would appear on the Bob Dylan album, but a more risqué one befitting the Greenwich Village counterculture. When the song’s narrator, a hayseed visitor to the Big Apple, describes an encounter with a crossdressing prostitute—“Well I got on the subway, took a seat / and got off on 42nd Street / I met this fella named Dolores there / He started rubbing his hands through my hair”—the crowd laughs uproariously, presumably in response to the comical image of the yokel caught off-guard by a trans woman turning tricks at Times Square. Clearly the Gerde’s audience is hip to the 42nd Street sex trade.
Dylan’s knowing satire of the yokel-and-Dolores in “Talkin’ New York” is only one example of the comedic and occasionally subversive early 1960s Dylan, who is well-documented on Through the Open Window. In this, the boxed set conveys both the ambiance of the downtown folk scene and Dylan’s ingratiation of himself to audiences through humorous crowd-work. As is well known, Dylan himself credited Charlie Chaplin as an influence on his early stage persona. Picking up on his Chaplinesque mannerisms, Shelton in 1961 described him as “both comedian and tragedian,” who embellished his Gerde’s sets with a “variety of droll musical monologues.” Hammond’s pseudonymous liner notes to Dylan’s 1962 debut further secured this association of Dylan with Chaplin, describing him as “nervously tapping his hat, adjusting it, using it as a prop, almost leaning on it,” in the manner of the silent film icon.[7]
In his own liner notes, Wilentz picks up on these themes by characterizing Dylan as a “droll singing comedian who could turn even a story occasion into a farcical frolic.”[8] His observation comes in the context of his discussion of a recording of “Talkin’ Bear Mountain Picnic Massacre Blues” from a September 1961 Gaslight Café performance. But he could just as easily have referenced Bonnie Beecher’s 1961 Minneapolis home recording of Dylan doing a comic shtick about East Orange, New Jersey (where his friends the Gleasons lived, not far from Woody Guthrie when he was at Greystone Park Psychiatric Hospital) or his version of “Talkin’ War III Blues” from a taped show at Cambridge’s Club 47 in April 1963.[9] Many eyewitnesses have described the comic Dylan of these early years. But experiencing Dylan’s sharp humor and excellent comedic timing on this newest boxed set is still fascinating, particularly for those of us (present writer included) who grew up with Bob Dylan-the-Legend and who discovered the looser, funnier Dylan only in retrospect. Through the Open Window presents listeners a Dylan who is quite different from the detached, often standoffish performer of the present.[10] The humorous, joking Dylan of the boxed set arrives at a moment when Instagram users, in response to this seemingly gloomier, glummer Dylan of the 21st century, have seized upon the photographic trope of “Bob Dylan smiling” as a humorous meme.[11]
This raises a series of questions: What happened to the Chaplinesque Dylan? Was he a casualty of the suffocating adulation of the early 1960s? By virtue of ending in late 1963, Through the Open Window is silent on such issues. On the other hand, it offers much to listeners interested in Dylan’s well-documented attraction to Black music and musicians, beginning with his teenage forays into Black pop. In particular, Through the Open Window highlights Dylan’s immersion in the recordings of Robert Johnson, whose work became newly available to folk revivalists with the 1961 release of the King of the Delta Blues Singers compilation. Dylan drew overtly on Johnson for the melody of his version of “Corrina, Corrina” (included here in a Gerde’s Folk City rendition); but Johnson’s influence can also be heard in Dylan’s explorations of his falsetto register. Although many of the tracks that register Dylan’s relationship to blues have been heard before, it is still interesting to revisit these early years of experimentation. How did Dylan approach songs that emerged from circumstances so utterly distinct from his own? How did he insert himself into songs of the wanderer, the outcast, the impoverished Southern laborer? By what imaginative leaps—or sleights of hand—did he discover himself in the blues, and how did he bend the music of Black America toward his own expressive needs?
But the young Dylan was not only “discovering” Black music on vinyl or shellac. Through the Open Window documents the young performer’s interactions with contemporary blues musicians including the Rev. Gary Davis, Big Joe Williams, and Victoria Spivey. As these tracks helpfully demonstrate, when Dylan arrived in New York in late 1961, blues was very much a living tradition, not an inert, romanticized art form. Spivey was particularly important to Dylan’s formation. The New York-based Blues Queen indulged his blandishments and invited him to play harmonica on March 1962 sessions with Big Joe Williams, later released on two albums from her own imprint. (Dylan would confirm the importance of Spivey’s mentorship by featuring a photograph of the two of them, from the very same 1962 sessions, on 1970’s New Morning LP.) “Wichita” and “It’s Dangerous,” the Spivey Records tracks included on Through the Open Window, thus helpfully recall the centrality of an older generation of Black musicians to Dylan’s—and other young white folk singers’—musical development. In that sense, the boxed set is a welcome rejoinder to A Complete Unknown’s disparaging depiction of the fictional bluesman Jesse Moffette, played by Big Bill Morganfield (Muddy Waters’ son). The blues singers Dylan knew in 1962—and who are pictured in images printed along with the Through the Open Window liner notes—would not have arrived on the set of the TV show Rainbow Quest disheveled, drunk, and clutching a whiskey bottle. They were dapper professionals, struggling to make a living from their art, even as a new generation of white musicians would ultimately come to profit from it.
In light of the boxed set’s reminders of the many Black people who scaffolded and supported Dylan’s early career, I found it hard not to detect a reference to interracial relationships in the lyrics to “Kingsport Town,” an arrangement of “Who’s Gonna Shoe Your Pretty Little Feet” here captured as an outtake from the November 1962 Freewheelin’ Bob Dylan sessions. “High sheriff on my trail boy / high sheriff on my trail,” Dylan sings, “All because I’m falling for / a curly dark-eyed gal.” The lyrics are traditional, recorded decades earlier by Woody Guthrie, but the phrase “a curly dark-eyed gal” evokes the African American women—including Mavis Staples and Delores Dixon—who attracted (or is rumored to have attracted) Dylan’s romantic interest in the early 1960s. Through the Open Window makes such questions possible, even if it cannot answer them.
I cannot end this review without mentioning Through the Open Window’s documentation of the quantum leap in Dylan’s songwriting between the period of “Talkin’ New York” and “Song to Woody,” the two originals on Bob Dylan, and his utterly self-assured Carnegie Hall performance of October 1963. The setlist of either half of that concert would have been enough to cement Dylan’s reputation as a major 20th-century composer: “The Times They Are A-Changin,’” “Boots of Spanish Leather,” “Blowin’ in the Wind,” “North Country Blues,” “A Hard Rain’s A-Gonna Fall” before the intermission, followed by “Don’t Think Twice, It’s All Right,” “Only a Pawn in Their Game,” “Masters of War,” and “The Lonesome Death of Hattie Carroll” in part two. It is genuinely thrilling to hear the Carnegie Hall set in its entirety, rather than through snippets stitched together from Live at Carnegie Hall (Columbia, 2005), earlier Bootleg Series releases (Vols. 1-3 and Vol. 7), and the ultra-rare six-LP set The 50th Anniversary Collection 1963 (Sony Music, 2013). After listening to them for this review, I would not revisit much of the material on the first six CDs of Through the Open Window. But I can imagine listening to the Carnegie Hall set for its immersive pleasure.
It goes without saying that the target audience of the Bootleg Series, currently retailing at $160 (list price) or $138.36 (on Amazon), consists almost entirely of people who do not need to be convinced of its merits. (That includes readers of this review.) It is impossible to find fault with the boxed set’s thesis that in a few remarkable years between 1959 and 1963, with the assistance of New York City and a large cast of musical mentors (both living and on recordings), muses, friends, and frenemies, Bob Dylan developed into a musician of great originality, interpretive intelligence, and lyrical subtlety. The overabundance of the boxed set only cements the narrative of the Hero’s journey. But that does not mean that we cannot peek through the open window to catch sight of less noticed aspects of his early career.
[1] The image is from a 1963 photo shoot by Ralph Baxter, who mostly placed Dylan in more terrestrial settings: standing at a corner at Gramercy Park, posing with a cigarette on a balcony overlooking a crowded urban courtyard.
[2] See Jacob Uitti, “Patti Smith Is Always Going to Be a Worker,” Interview, October 20, 2020. https://www.interviewmagazine.com/music/patti-smith-is-always-going-to-be-a-worker
[3] See https://www.mojo4music.com/articles/new-music/bob-dylan-the-bootleg-series-volume-18-review-dylans-miraculous-new-york-transformation/ and https://www.uncut.co.uk/reviews/bob-dylans-through-the-open-window-the-bootleg-series-vol-18-1956-1963-reviewed-documenting-the-dawn-of-a-legend-151807/. While track-by-track discussions of “Through the Open Window” began popping up online after the stroke of midnight on October 30, 2025, I particularly benefited from Ray Padgett’s detailed listening guide—sent to subscribers of his “Flagging Down the Double E’s” newsletter.
[4] Here I mean to differentiate the romanticized image from the notion of Dylan’s exceptionalism as a musician.
[5] Robert Shelton, “Bob Dylan: A Distinctive Folk-Song Stylist,” New York Times, September 29, 1961.
[6] “In the dead of the night, he would wake up, grunt, grab a cigarette, and stumble over to the typewriter … turning out songs like ticker tape.” Joan Baez, And a Voice to Sing With: A Memoir (New York: Simon & Schuster, 1987), 86.
[7] Billy James, “Bob Dylan: The First Interview, October 1961, available at https://www.rocksbackpages.com/Library/Article/bob-dylan-the-first-interview; Robert Shelton, “Bob Dylan: A Distinctive Folk-Song Stylist,” New York Times, September 29, 1961; Stacey Williams (John Hammond), liner notes, Bob Dylan (Columbia Records, 1962).
[8] Wilentz, p. 28.
[9] Some of this material appeared on The Bootleg Series, Vol. 1-3: Rare & Unreleased 1961-1991 (Columbia Records, 1991) or The Bootleg Series, Vol. 9: The Witmark Demos: 1962-1964 (Columbia Records, 2010).
[10] I am thinking of the Dylan of the fall 2025 Outlaw Music Festival, who seemed to intentionally hide from the audience. See the “‘I’m Not There’: Why is Bob Dylan Hiding?” (September 14, 2025) episode of Laura Tenschert’s Definitely Dylan. https://www.definitelydylan.com/podcasts/2025/9/14/zu3x709n5k6gifhcha53kt3w039e8i
[11] See, for example, the Instagram account of dylan.ologist. https://www.instagram.com/p/DA3AfODRliZ/
