After several volumes delving into distinct stages of Bob Dylan’s career, it took the Bootleg Series fifteen years and nine volumes before they went back to the beginning. Through The Open Window aims to tell the definitive story of his origin only touched on by his first three albums (and subsequent archival releases). The years stated on the cover span 1956 through 1963, but after a 15-year-old Bobby Zimmerman pounding Shirley & Lee’s “Let The Good Times Roll” on a St. Paul music store piano and an acoustic ditty called “I Got A New Girl” three years later, the program really begins in 1960, where a college slacker has discovered Woody Guthrie. Before the end of the first disc he’s already made it to the Gaslight CafĂ© and Gerde’s Folk City in Greenwich Village. He enters a recording studio to blow harmonica on a Carolyn Hester session, plays a concert above Carnegie Hall, and two months later records his first album over two days. (Two familiar outtakes are included, along with two alternates, and a previously unreleased cover of Woody’s “Ramblin’ Round”.)
All the while, he’s learning how to pick guitar and play harmonica at the same time, memorizing song lyrics and attempting to write his own, and fabricating his own back story, as alluded to in the baffling “Dusty Old Fairgrounds”. Many of the selections are informal recordings, included more for historical purposes, far away from studio microphones and settings, so there are flubbed strings, off-key instruments, and the sound of a 20-year-old kid trying to sound four times his age (save a salacious ad-lib in a version of “Cocaine”; the compilers chose not to include any of the VD songs Woody wrote). When an audience is present, they are fascinated, and collaborators like Jim Kweskin and Dave Van Ronk clearly like what he has to offer. And we get to hear him improve and develop in a fairly short time.
By the third disc he’s moved on from aping Woody on vintage folk and blues songs, and started writing more topical songs about social injustice. After more harmonica work for Harry Belafonte, Victoria Spivey, and Big Joe Williams, he starts to record his second album. But it takes a while to complete, as he can’t decide whether it should be all protest songs (like the earlier, edgier “Ballad Of Hollis Brown”) or if he wants to rock out, which is why he attempts the familiar “That’s All Right Mama” and his own “Mixed-Up Confusion” with a band, eventually settle for just Bruce Langhorne on second guitar. “Worried Blues” is tried out on a 12-string, and “(I Heard That) Lonesome Whistle” shows off his Hank Williams yodel.
Come 1963, the surviving minute of his appearance on a British TV show kicks off disc five. After his April show at the Town Hall show—about a third of which is here, out of order, and including repeats of “Tomorrow Is A Long Time” and “Last Thoughts On Woody Guthrie”—he comes up with the last handful of songs, a fresh mix of protest and personal, needed to finish the Freewheelin’ album. But by the summer, he was caught up in the civil rights movement, with appearances at voter rallies and the March on Washington, and made a big splash at the Newport Folk Festival. He also made a big splash with Joan Baez, who sang with him every chance she got; three of their duets are included here, including the only known performance of “Troubled And I Don’t Know Why”.
Angrier topical songs would dominate his third album, though he was also writing songs like “Farewell”, “Liverpool Gal”, “Boots Of Spanish Leather”, and “One Too Many Mornings” (the latter two heard in alternate takes) and banging the piano for “Key To The Highway” and “Bob Dylan’s New Orleans Rag”. The final two discs contain his complete Carnegie Hall concert in October 1963, twenty years after it was first teased on a promo CD. It’s a good place to finish, as that third album would come out in the first few weeks of 1964, when everything changed, and for him too. Most of the songs in the set weren’t on albums yet, so they’re fresh for the crowd, but the performance would only reinforce his image as a protest singer and nothing but.
Some of this music had circulated on bootlegs for decades, but never in this quality. Through The Open Window of course only scratches the surface of what has survived from this period, and the individual listener will have their own missing favorites (for us it’s “Black Cross” and the electric “Rocks And Gravel”) in addition to resentment over repetition, both in song choice and things that had already appeared on earlier volumes and copyright releases. As had been the label’s habit, a two-CD “highlights” condensation was also made available, but we always wonder who would actually spring for those outside of completists. With most Bob, you’re either all in, or out.
Bob Dylan Through The Open Window: The Bootleg Series Vol. 18 1956-1963 (2025)—3






