On The Bootleg Series Vol. 18: Through The Open Window, 1956-1963, Bob Dylan continues his ongoing archival releases with a new installment focused on his early days as an aspiring singer-songwriter. Out Friday, Oct. 31, this eight-disc, 139-track set is of particular interest to Minnesota music fans because it contains a treasure trove of more than 20 primitive and unreleased home recordings made in his hometown of Hibbing and at a series of house parties and intimate venues, mainly at and around the University of Minnesota’s Twin Cities campus.

A good portion of this collection focuses on Dylan’s time before he moved to New York in 1961 – including a recording from a St. Paul music store on Christmas Eve, 1956. In later discs, there are plenty of recordings from his times returning back home after making a name for himself in the burgeoning Greenwich Village folk scene.

We researched the various home recordings, house party performances, and informal material made in Minnesota featured on Through the Open Window. Here’s more detail on the circumstances behind these early covers and original songs, the venues where these tunes were taped, who was in the room, and what led up to the unguarded moments where these fabled sessions took place.

Terlinde Music Shop, St. Paul – December 24, 1956 (Disc 1)

On Christmas Eve in 1956, a 15-year-old Bob Zimmerman, his cousin Howie Rutman, and friend Larry Kegan paid $5 to record an eight-minute medley of songs. They called themselves the Jokers on the double-sided acetate recorded at Terlinde Music Shop, which was located on West 7th Street (AKA Fort Road) only a few steps from where Grand Casino Arena now sits in downtown St. Paul. On what is Bob Dylan’s first known recording session, Zimmerman was on vocals and piano, with Rutman and Kegan on vocals. Their rollicking, if rough-sounding, take on the Shirley & Lee 1956 hit, “Let the Good Times Roll,” kicks off The Bootleg Series Vol. 18: Through the Open Window.

In The Double Life of Bob Dylan, author Clinton Heylin writes, “The Jokers was a real combo, playing high school dances and dreaming of greater things,” while Rutman recalls, “We were hugely ambitious, and we really wanted to do stuff.” The rest of the recording session included the Jokers’ 30- to 40-second renditions of classics from the era, like “Boppin' the Blues” by Carl Perkins & Howard Griffin, “Lawdy, Miss Clawdy” by Lloyd Price, and “In the Still of the Night” by the Five Satins. Apparently, a copy of this precious acetate belonging to the estate of Larry Kegan was put up for sale on eBay in 2002, but the reserve price of $150,000–$200,000 was not met and it went unsold. The acetate is now believed to be in Dylan’s possession.

Home of Ric Kangas, Hibbing, Minnesota – May 1959 (Disc 1)

The 1959 bedroom recording of the Dylan original, “I Got a New Girl” (also referred to as “Teen Love Serenade”), is the only Through The Open Window selection recorded in his hometown of Hibbing. The 17-year-old Zimmerman had visited high school friend Ric Kangas to record four songs using a reel-to-reel recorder and high-quality Shure microphone. Dylan contributed guitar and vocals and backed up Kangas on one of his tunes, "I Wish I Knew," while leading the way on "I Got a New Girl," “When I Got Troubles,” and a song that Kangas humorously called, "The Frog Song," because that was how Dylan's voice sounded that day.

Kangas says they bonded over a shared love of Hank Williams and early rock 'n' roll, while Dylan introduced Kangas to the blues, Jimmy Reed, and the Coasters. They drove around listening to music, and Kangas dropped the aspiring songwriter at a local radio station where he convinced the DJ to play one of his songs on the radio for the very first time. "One thing about Bob was he was always excited about things, particularly music,” Kangas said of Dylan. “It was fun to be around someone so upbeat about the things that he loved." Two songs from Kangas’ bedroom recordings were used in Martin Scorsese's 2005 Dylan documentary, No Direction Home, and Ric tried auctioning off the reel-to-reel in 2006, but it was ultimately withdrawn after failing to meet its reserve price.

Home of Bob Dylan – September 1960 (Disc 1)

Through the Open Window includes a 19-year-old Dylan covering Woody Guthrie's "Jesus Christ" and Jesse Fuller’s “San Francisco Bay Blues,” during a gathering at his Minneapolis apartment above Gray's Campus Drug in Dinkytown. Cleve Petterson is credited with recording the songs on his Realistic reel-to-reel tape recorder.

The same device was used to capture a recording filed as “Minnesota Party Tape,” archived at the Minnesota Historical Society, where visitors can listen for free at the Gale Family Library in St. Paul. This tape captures Dylan singing and playing guitar over a 13-song house party performance featuring the two songs mentioned above. According to the Historical Society’s documentation, other attendees that night included Dinkytown folk scenester Bill Golfus, activist and actress Bonnie Beecher (more on her later), and Cynthia Fincher, who occasionally played banjo with Dylan during his gigs at the Purple Onion, a pizza parlor that was near Hamline University in St. Paul.

On these box set selections, the sound quality is rough, but Dylan’s distinctive voice was emerging, albeit with obvious influence from Guthrie. He mutters, “hmmm,” after finishing “Jesus Christ” on the box set, as if he is contemplating if he did the song justice. Then he affectionately says, “That’s Woody,” to identify that the song was written by his idol.

Coffman Memorial Union, University of Minnesota – May 13, 1961 (Disc 1)

After some time in New York City, Dylan returned to campus to play a creative arts and folk festival at Coffman Union. Again, he covered Guthrie and effectively incorporated harmonica for his version of the 1940 Dust Bowl Ballads standout, “I Ain’t Got No Home.” Dylan playing gigs in Greenwich Village clubs had also strengthened his singing voice considerably. Dylan turned 20 just 11 days after this Coffman Union performance, and began recording his self-titled debut album for Columbia Records six months later.

Notably, Dylan returned to “I Ain’t Got No Home” at the January 1968 event, A Musical Tribute To Woody Guthrie, at Carnegie Hall in New York City. The concert honored the folk legend, who passed away a few months prior, with Dylan’s appearance marking his first public performance in 18 months following his notorious motorcycle accident.  

House Party – May of 1961 (Disc 1)

While Dylan was back in Minnesota for the folk festival appearance, he played a house party, likely at the Dinkytown home of actress/musician Bonnie Beecher, a longtime friend. Two songs from that set — a truncated cover of Reverend Gary Davis’ blues classic “Death Don’t Have No Mercy,” and a rollicking take on Bess Lomax Hawes’ “Devilish Mary” — are included on Through The Open Window. Dylan seemed to be instructing the party-goers about the chords and structure of Davis’ tune, finishing the song early while muttering, “That gives you some sort of an idea of how it goes.” There are brief moments of him getting lost in the song’s emotion, hinting at the Dylan of the future.

House Party – Home of Bonnie Beecher, December 22, 1961 (Disc 2)

The recordings from this party at Beecher’s home included on this box set were part of the legendary bootleg, the Minnesota Hotel Tape (also included on the notorious Great White Wonder bootleg circulated in Los Angeles in 1969). Dylan often referred to Beecher’s apartment as the Minnesota Hotel because he crashed there whenever he came back home. This section starts with Dylan telling a comical story about performing in a chess-playing coffee house in East Orange, New Jersey, noting “it’s a horrible town.” He was growing more comfortable in front of an audience, which included creating a mythology about himself to serve his music and persona.

The music included is an exceptional glimpse into a musician ready to take that next step. Dylan had just recorded his self-titled debut album — which would be released in March 1962 — and he even played “Baby Let Me Follow You Down” at the house party. His original tune, “I Was Young When I Left Home” is a showstopping highlight of this collection. It is a deeply moving song about leaving behind everything you know for the thrill of the unknown, performed in the very home that Dylan had left behind for New York. Dylan’s resonant, poignant lyrics, “I was young when I left home / And I been out ramblin' 'round / And I never wrote a letter to my home,” ultimately serve as the belated communication that he failed to send.

The rest of Dylan’s relaxed and stellar set is filled with traditional folk covers, including “Dink’s Song” AKA “Fare Thee Well,” which has also been performed by Joni Mitchell, Jeff Buckley, Marcus Mumford, Joan Baez, and Burl Ives, among others. These recordings are a crucial musical document of Dylan’s formative years.

Home of Dave Whitaker – August 11, 1962 (Disc 4)

A trio of songs on the box set were recorded in the summer of ‘62 at the Minneapolis home of Dylan’s longtime friend Dave Whitaker using his pal Tony Glover’s tape recorder. It starts with Dylan telling a story about his girlfriend, Suze Rotolo — featured with him on the cover of The Freewheelin' Bob Dylan, which he was recording at the time. She was on a European vacation, “and until she’s back, I never go home. It gets kinda bad sometimes.” The story is a tender introduction to an early version of “Tomorrow Is a Long Time,” that is fragile and emotional.

The other tunes from this recording include the last verses of “This Land Is Your Land,” which Dylan reverently says, “Woody Guthrie sang to me these verses here, which nobody ever sings.” Dylan then introduces his original tune, “Long Time Gone,” by announcing, “Nobody has ever heard this one, this is the first time I’ve sung it.” And after he’s finished playing it, he proudly proclaims, “I wrote that for myself! I figured I’ve been writing too many songs for other people.” This tender lament about leaving home has sprawling lyrics that stretch from Western Texas to the side of the highway, from the crossroads all the way to the grave. Dylan had so many vital things to say in that time that “Long Time Gone” isn’t on any of his studio albums, but thankfully it is included on Through The Open Window. 

Home of Dave Whitaker – July 17, 1963 (Disc 6)

Dylan’s landmark Freewheelin’ record was released less than two months before another fun, collaborative performance at Whitaker’s home – again documented by Glover. (A few weeks later, Dylan began recording The Times They Are a-Changin'.) The highlight of the three songs included from this session is the never-before-heard tune, “Liverpool Gal,” which Dylan wrote about his first time in England seven months prior.

 He shared another new original song, “Eternal Circle,” which he confidently introduced, “Now here’s a song that you would never get unless you actually did this. This is just about a guitar player.” The lyrics detail a musician winning over a girl watching him play. In the story, the tune dragged on for too long, and by the time he finished playing, she was long gone. 

The set also features an upbeat collaborative jam between Dylan and Glover titled “West Memphis.” This is the final recording made in Minnesota featured in the box set, with the remainder of the collection focusing on outtakes from Dylan’s legendary recording sessions at Columbia Studios in New York, as well as his entire iconic performance at Carnegie Hall in October 1963.

By that point, Dylan had already made an indelible mark on popular music. And, as this set shows, his tentative early recordings in Minnesota were integral phases in his world-changing evolution. Obsessives will find a lot more detail from the era in the Through the Open Window: The Bootleg Series, Vol. 18 box set’s 124-page hardcover book with extensive liner notes by Sean Wilentz and over 100 rare photographs.