This year, Bob Dylan fans across the world will have had an especially happy Halloween—the Dylan camp decided to dispatch the 18th edition of The Bootleg Series, which compiles unreleased songs and alternative versions of existing ones, on Friday.

Following the release of the Dylan biopic, A Complete Unknown, which focused on the genesis of Dylan’s career in Greenwich Village, The Bootleg Series Vol. 18: Through the Open Window 1956–1963 (Highlights) features Dylan’s earliest experimentation as a musician.

The full bootleg is extensive, but the highlighted, freely available version has 42 songs. A notable percentage of these are new to official streaming platforms, and, for many, are being heard for the first time. Of course, Dylanologists can find, and have found, almost everything online, compiling makeshift discographies on niche internet sites like Expecting Rain.  

For most people, songs like “Blowing In The Wind,” and “Don’t Think Twice it’s Alright” from Dylan’s second album are what define his music and, subsequently, his persona—it’s why the biopic follows this early period. 

Because of the years covered in the bootleg, the songs reaffirm the picture of Dylan as a scrappy young singer idolizing Woody Guthrie. The tunes are relentlessly folky and will appease the masses: Dylan analysts and more casual fans alike. 

The first couple tracks are an insight for very serious fans into the early musical whims of Dylan, but aren’t really listenable. The bootleg’s opener, “Let the Good Times Roll,” features a crumbly, minute-long audio recording of 15-year-old Dylan jamming playfully with a friend in a music shop. The following track, “I Got a New Girl,” is a complete song, but is similarly let down by the audio quality.

The third track, “Jesus Christ,” is where things start to get good. While many narrow Dylan’s evangelical musings down to his “Christian phase” at the start of the ’80s, this 1960 recording displays religious consciousness earlier on. But the song is a polemic written by Guthrie, so the performance is more of a tribute to his idol than a foreshadowing of his future “conversion.”

“K.C. Moan (with Danny Kalb),” written by the Memphis Jug Band, is sung in jaunty duet with Danny Kalb, one of Dylan’s many folk contemporaries, who he would quickly overshadow. “Railroading on the Great Divide (with Jim Kweskin)” has a similar feel, and also features a largely forgotten folk singer.

Ever since the release of Bob Dylan: Don’t Look Back, the D.A. Pennebaker documentary following Dylan’s 1965 England tour, fans have been waiting for an official Dylan rendition of “Remember Me.” In the documentary, there are many scenes of Dylan jamming or writing in various hotel rooms and other in-between spaces, as people chat in the background and smoke.

In one such impromptu session, Dylan sings “Remember Me.” It’s a fantastic rendition, full of sorrow and yearning, made into an incredibly beautiful and ephemeral moment of music by the heavenly harmonizing of Joan Baez, who comes in toward the end. 

The absence of Baez on the bootleg’s “Remember Me” means the incredible duet will remain transcendent, existing only in that minute of film. But it’s still great, and given that fans have been waiting six decades for an official release, there will be no complaints.  

The song fits perfectly a certain genre of Dylan’s early music, one which results from his peripatetic lifestyle at the time—moving from Duluth to New York City, and then to stardom. Wherever he is, somehow he’s already gone. Permanence is out of Dylan’s grasp, and as a result, love has been lost. But maybe it always was.

“The saddest words I ever heard were words of parting / When you said ‘Sweetheart, remember me,’” sings Dylan.

Tracks 10 through 15 are all from a recording session at the home of Bonnie Beecher, an actress and girlfriend of Dylan. While there are existing versions of them all already, these recordings have a particularly melancholic feel, whether Dylan is singing elegiacally about Lazarus, or ruminating on drugs and addiction, as he does in the tragic “Cocaine.”

“It must be good for somebody, this sorta song. I know it’s good for somebody. If it ain’t for me, ‘least it’s good for somebody,” says Dylan, in the intro to “I Was Young When I Left Home.” 

This bootleg’s live version of “Talkin’ New York” has significant lyrical differences from the album version, but is both as humorous and as poignant. Also with significant lyrical change is “Tomorrow Is a Long Time,” recorded in the home of Dave Whitaker. While it’s not better than the version on Bob Dylan’s Greatest Hits Vol. II, seeing Dylan play with the word choice and structure of a song is always fascinating.

“Man Of Constant Sorrow” is an absolutely iconic folk song. From Peter, Paul, and Mary to the Soggy Bottom Boys, it has been covered extensively. Dylan had two existing versions prior to this bootleg, from his debut album and the No Direction Home soundtrack, but this new edition is the best of the bunch. 

Unlike some other covers, the narrative voice in Dylan’s versions has an ambiguous past.

“I bid farewell to Colorado / Where I was born and partly raised,” sings Dylan. 

The uncertainty regarding where he was raised feels apt for Dylan in 1961—a person using a pseudonym, claiming to have rode a boxcar to New York and been taught guitar by cowboys. Despite being from Duluth, he didn’t believe it meant anything. He was reinventing himself completely on the way to becoming a man with no past.

The song’s outro features an interaction between Dylan and, presumably, his producer, which feels like a scene straight out of the recent biopic. Dylan, looking to sound older than he is, gives elusive, playful responses to simple questions.

“Has it been recorded?” the unnamed man asks. “Not that way,” says Dylan.

Slightly less predictable than the others, and slightly more interesting because of it, this version of “A Man of Constant Sorrow” isn’t revolutionary. I mean, how could it be? The song was written over a century ago. But it is great folk music. 

And that is, in a way, what this bootleg is: fantastic folk but not much more. Despite the early music’s popularity, young Dylan is far from the best version of himself, musically. Still more or less a Guthrie imitator with a few brilliant originals, Dylan hadn’t done anything completely fascinating yet.

Nevertheless, Through The Open Window is full of wholesome, folky spirit. A nostalgic return to a period of his music and character long gone, it offers a window into the vagabond ramblings and musical intent of a young Dylan which will excite a range of fans.