Why Didn't Bob Dylan Release These Songs?
They would have completely reshaped five of his albums.
The title is a misnomer, of course. Bob Dylan has been releasing lost treasures for decades now as part of his expansive Bootleg Series, which dates back to 19911. There are official versions of many previously unissued white-whale tracks.
Still, it’s worth examining the times when an extra song, left off for utterly inexplicable reasons, might have saved an only-OK album – or, as in the case of Time Out of Mind and Oh Mercy, made a great one even greater.
That’s no small part of Dylan’s mystery and myth. With other acts of his era, most notably on the Beatles’ Anthology set, a deep dive into outtakes, leftovers and demos only serves to underscore just how perfect the final product typically was. With Dylan, there seem to be endless variations, and many of them are just as resonant.
Looking back, the addition of just one more song might have forever changed the fate of five finished Bob Dylan LPs:
"CARIBBEAN WIND," (SHOT OF LOVE, 1981)
A prompt release of this six-minute epic would have enlivened one of Dylan's also-ran albums, while also revealing perhaps the exact moment in which Bob Dylan began to turn away from the deflating fundamentalism of the late-1970s. (No small thing.) A kind of 1980s update of “Visions of Johanna,” “Caribbean Wind” was unsuccessfully worked and re-worked for Shot of Love before Dylan finally seemed to find the center of the song during a 1980 tour. Five years later, “Caribbean Wind” showed up on Biograph, somehow revealing yet another tossed-aside rewrite.
“BLIND WILLIE McTELL” (INFIDELS, 1983)
There may not be a more head-scratchingly strange omission than “Blind Willie McTell,” which wouldn’t see the light of day until its release on the initial Bootleg Series project. Infidels was certainly poorer for it2. But the song, a kind of “St. James Infimary”-esque eulogy not just for the musical craft of Blind Willie McTell but for a nation’s innocence in the era of slavery, clearly vexed Dylan. He tried several approaches during these Mark Knopfler-helmed sessions but couldn’t seem to get a handle on things. That is, until he heard the Band’s take from 1993's Jericho, after which Dylan began regularly performing “Blind Willie McTell” with a very similar arrangement.
“WHEN THE NIGHT COMES FALLING FROM THE SKY,” (EMPIRE BURLESQUE, 1985)
An apocalyptically scarifying rocker, “When the Night” was wrecked by the disco-sheened version that finally showed up on the official release – one of the worst decisions in a decade stuffed with them. About the only thing worth noting was background vocalist Madelyn Quebec’s dusky asides. Contrast that with the scorching original take, recorded at the Power Station with Steven Van Zandt and Roy Bittan of the E Street Band. Dylan apparently came to grips with his misstep later, offering a series of tough live updates through his 1986 tour with Tom Petty, beginning with a simmering vocal showcase before exploding forward with the Heartbreakers.
“SERIES OF DREAMS,” (OH MERCY, 1989)
As celebrated as this album was in its moment, there's little question that the inclusion of “Series of Dreams” would have made Oh Mercy better – as, perhaps, would have the similarly shelved “Dignity.” But with “Series of Dreams,” Bob Dylan left behind something (like the subsequent “Dreamin’ of You”) that could have provided a sharp outline for his entire New Orleans fever-dream of an album. The struggles over this song, like much of Oh Mercy, were legend. (Producer Daniel Lanois was pushing for an extended passage in the style of the bridge.) By the end, Dylan had clearly come to question whether the song was worth all the trouble. Remixes and demos from the Bootleg Series illustrated once more than it most certainly had been.
“DREAMIN' OF YOU,” (TIME OUT OF MIND, 1997)
Finding much fault at all with this late-period gem seems ungracious, but even masterpieces – think the Beatles’ Sgt. Pepper’s Lonely Hearts Club Band with the addition of stand-alone 1967 singles “Penny Lane” and “Strawberry Fields” – can sometimes be improved. “Dreamin’ of You,” eventually issued on Bootleg Series Vol. 8, would have similarly framed and perhaps even extended the central themes of Time Out of Mind, which dealt so frankly with the idea of lingering passions and looming departures. In fact, a line like “even if the flesh falls off my face, it won’t matter if you’re there” works as a kind of flinty summation.
Amazon best-selling rock band biographer Nick DeRiso’s next book, ‘Forever Young: How the Band and Bob Dylan Made the Only ’60s Music That Still Matters,’ will be released in Spring 2025. www.nickderiso.com.
This series also changed our understanding of Bob Dylan and the Band.
Infidels did, however, feature a conundrum of a song that pointed to bigger things.