Listening to Bob Dylan’s early years

Just how surprising or enlightening you find Sony Legacy’s latest Bob Dylan box, The Bootleg Series Vol. 18: Through the Open Window, 1956–1963, depends on how much you’ve already investigated the nooks and crannies of Dylan’s un- or semi-official discography.

Unlike most of the Bootleg Series, the majority of Through the Open Window’s 139 performances (as well as some of the 26 song intros, interview excerpts, and jokes) have been circulating for awhile. Thirty-eight of the performances first went legit on the copyright-extending 50th Anniversary Collection 1962 (2012) and The 50th Anniversary Collection 1963 (2013) while another 43 did so on 18 other albums beginning with Broadside Ballads Vol. 1 (1963), ending with the Inside Llewyn Davis soundtrack (2013), and poaching three other volumes of the Dylan Bootleg Series in between.

The number of previously unreleased performances would therefore appear to be 58. Yet even that tally might be high if you count the tracks that have already circulated on literal Dylan bootlegs such as Great White Wonder (1969) and Ten of Swords (1985).

So if the target audience isn’t die-hard Dylan collectors, who is it? Easy: the millions of Gen Zers who helped James Mangold’s 2024 biopic A Complete Unknown make bank. The young-Bob period portrayed in that film and the young-Bob period curated on Through the Open Window don’t overlap exactly, but they overlap enough.

The eight-disc set begins with a ­snippet from a record that 15-year-old Bobby Zimmerman and two friends made at a St. Paul, Minn., music store on Christmas Eve, 1956. The song (Shirley and Lee’s “Let the Good Times Roll”) goes by fast, but there’s no denying the voice. Discs 7 and 8 contain the Carnegie Hall concert Dylan performed after his second album and Peter, Paul and Mary’s recording of “Blowin’ in the Wind” had made him famous. How he went from the St. Paul store to the NYC Hall in just under seven years is the story the box tries to tell.

It’s an episodic tale for sure. One minute, Dylan’s playing harmonica for Harry Belafonte, Carolyn Hester, or Victoria Spivey, the next he’s writing “The Death of Emmett Till” and “Ballad of Hollis Brown.”

There is, however, a unifying thread, and it isn’t so much folk or protest but humor. Whether delivering talkin’-blues songs, telling the East Orange chess club story, or foreshadowing Norm Macdonald with a rambling intro to “Tomorrow Is a Long Time” at Town Hall in April ’63, young Bob sure knew how to get laughs.