‘Caribbean Wind’ (1981)

For each great song that Dylan has released, and he has released more than his fair share, he has also left one on the cutting room floor. Since the 1960s, Dylan has been the most bootlegged artist in history, and thanks to the extensive archival releases that Dylan Inc and Sony Legacy collate with such regularity for The Bootleg Series, we now have easy access to so many of the songs that most other artists would build a career out of, but which Dylan didn’t even finish or make room for on an album.

Before Jeff Rosen began work on the Bootleg Series in the early 1990s, though, there was Biograph. In 1985, Dylan’s star was starting to fade, but Columbia Records still knew that he was one of the all-time greats and could draw an audience and make their money with the right material. To celebrate his career, they compiled a mammoth 53-song box set out of album tracks, live recordings, outtakes, oddities and rarities. Of the 53 recordings, 18 had never previously been officially released, and some had not even made their way onto unofficial bootlegs.

One of these unreleased recordings was Caribbean Wind, an outtake from 1981’s Shot of Love. Dylan extensively reworked the song’s music and lyrics during the recording sessions for the album, and tried to wrestle control of this swirling epic over a series of months. His notebooks from the time reveal that he continuously re-wrote and re-approached the song, and even played it live a few times—including one night with a guest guitar part supplied by Michael Bloomfield, which was ultimately the final public appearance from the legendary guitarist who had back Dylan at Newport in ’65 and played on the studio version of ‘Like a Rolling Stone’—but the song got away from Dylan and he hasn’t ever returned to it since.

‘When the Night Comes Falling From the Sky’ (1985)

A lot of the criticism against Dylan’s eighties output is levelled against the sound, feel and production of his albums, but his song-writing was as sharp as ever. If he had recorded ‘When the Night Comes Falling From the Sky’ at the sessions for Highway 61 Revisited or for “Love and Theft”, it would rightly be celebrated as one of his all time great story songs.

A raging epic, this opens with the familiar chord sequence that Dylan had previously used on both ‘All Along the Watchtower’ and ‘Hurricane’ and the song should be as well regarded as either of them. There are not only so many fantastic individual lines, but they equally come together to create an overwhelming and powerful cascade of images and sequences in the song.

The track was initially recorded with backing supplied by Bruce Springsteen’s E-Street Band, but that version was ditched in favour of the finished version, which can be found in 1985’s Empire Burlesque. The best, most thunderous versions were saved for the stage, though, when Dylan was backed by Tom Petty & The Heartbreakers.

‘Blind Willie McTell’ (1983)

“I was around during the sessions for ‘Infidels,’ and I fell in love with the song ‘Blind Willie McTell’” said journalist and Rolling Thunder Revue alumni Larry ‘Ratso’ Sloman. “When the album was finished, Bob called me up and asked me if I wanted to come over to hear it. He played it for me, but no ‘Blind Willie McTell.’ I asked him, ‘What gives, Bob? Where’s ‘Blind Willie McTell?’ And, without missing a beat, he goes, ‘It’s no big deal, Ratso. It’s just an album. I’ve made twenty-two. And I’ll make more.’”

‘Ratso’ wasn’t the only one who was baffled by Dylan’s decision to leave this song off of Infidels. To make matters worse, it wasn’t even the only outtake from the album, which was better than some of the released songs. ‘Too Late/Foot of Pride’, ‘Lord, Protect My Child’, ‘Tell Me’ and ‘Someone’s Got A Hold Of My Heart’ were all either as good as, or better than, the turgid ‘Neighborhood Bully’—maybe Dylan’s worst ever song—or ‘License to Kill’ and ‘Union Sundown’, all of which made the finished album.

But of the lot, ‘Blind Willie McTell’ is by far the best. One of Dylan’s most vivid lyrics and one of his most powerful performances, this song is a haunting reflection on America’s troubling past and its uncomfortable legacy of slavery, repression, and racism.

Built around the melody from the traditional blues piece ‘St James Infirmary Blues’, Dylan sings like a spirit himself. “I know no one can sing the blues like Blind Willie McTell”, he sings here in the refrain, but equally, no-one can sing American music like Bob Dylan.

‘Jokerman’ (1983)

One of the great songs which did make its way onto Infidels, and which became the albums opening track, ‘Jokerman’. The record is often spoken as being Dylan’s return to secular music after his Christian conversion and gospel detour of 1979, 1980 and 1981, but there are some discrepancies with that narrative. The first is that 1981’s Shot of Love, an album that Dylan has said is his favourite out of his own releases, is more of a rock and roll record than it is gospel, and the second is that the Good Book is all over Infidels, and nowhere more than on Jokerman.

Not only does Dylan directly reference Leviticus and Deuteronomy in the lyrics, but there is religious iconography all over the song, from the very opening line about “standing on the water” and its later images of snakes, angels and preachers.

Dylan later played the song in one of his most celebrated ever television performances, and wildly transformed its quasi-reggae rhythm of the album into a raucous, blistering garage rock number. Not only was Dylan writing just as great as ever in the 1980s, he was also just as creative and inventive when it came to reworking his best songs, too.

‘Every Grain of Sand’ (1981)

The closing track from Shot of Love, and also the closing track at almost each and every one of his recent Rough and Rowdy Ways World Wide Tour 2021-2024 shows, ‘Every Grain of Sand’ is one of the most important songs in Dylan’s entire career.

It is not just a lyric but can act as his mission statement and his manifesto. It is the distillation and embodiment of his driving force and his life and the culmination of his art. It is the song that explains all the others, and that explains why his work has such a profound and lasting effect on those who it truly touches. Written halfway through his life, the lines have only taken on deeper meaning and become more keenly resonant and impactful as he has aged.

“I am hanging in the balance of a perfect finished plan” Dylan sings at the end of the song, at the end of the album and now, at the end of all of his shows. “Like every sparrow falling, just like every grain of sand”.

‘Tight Connection to My Heart (Has Anybody Seen My Love?)’ (1985)

Of all the genres that you associate with Bob Dylan, whether it’s folk, blues, country or rock and roll, synth-pop is not one that usually springs to mind, but that’s exactly what this delightful surprise of a song is.

Opening with a beautiful chorus of voices supplied by Dylan’s backing singers The Queens of Rhythm, the track brilliantly blends the synthesised sounds of the time, funky guitars and an insistent rhythm with Dylan’s voice and words. And, like so much of Dylan’s work, those words might just be the best part of the song. Featuring a collection of fantastic lines and evocative images, if the 80s production is not for you, then the undeniable quality of the writing comes through in the stunning performances of this song by Sheila Atim from the Conor McPherson jukebox musical Girl From the North Country.

The lead track from Empire Burlesque, the song is notable for its wild and wildly fun music video. Directed by Paul Schrader, who was fresh off the back of co-writing the screenplays for Martin Scorsese films Taxi Driver and Raging Bull, and shot on location in Tokyo, Japan, the video really needs to be seen to be believed.

‘Most of the Time’ (1989)

One of Dylan’s most devastating and heartbreaking songs from Dylan’s entire career, this is a love song—or is it an anti-love song?—in the vein of ‘Don’t Think Twice, It’s Alright’, ‘Abandoned Love’ or ‘Love Sick’ or could even be seen as a modern update on the timeless Hoagy Carmichael tune ‘I Get Along Without You Very Well (Except Sometimes)’.

“I don’t cheat on myself, I don’t run and hide” Dylan sings, “hide from the feelings that are buried inside. I don’t compromise, and I don’t pretend. I don’t even care if I ever see her again” and then he takes a breath and adds the desolate and harrowing titular phrase, “most of the time”.

Added to the depth of the lyrics is the depth and the defeat in Dylan’s voice. His delivery is note-perfect and is as destructive and resigned to his fate as the words he’s singing. The fact that his age and his weariness is starting to creep into his cracking and creaking singing voice only adds more poignancy and power to the performance.

‘What Can I Do For You?’ (1980)

When people think of Dylan, they will usually think of a man with an acoustic guitar across his body and a harmonica holder around his neck. Dylan even apparently once quipped that “the harmonica is the world’s best-selling musical instrument. You’re welcome!”

The instrument has become synonymous with his image and his work, and even gave him his first taste of a recording studio, when he was recruited to play harmonica for Harry Belafonte’s Midnight Special album in the early 1960s. When you see Dylan in concert now, the first notes that he blows on the harmonica on any given night will elicit a roar of approval from the audience.

He has cultivated his own unique and idiosyncratic style with the instrument over the years, and gave his greatest performance with it on ‘What Can I Do For You?’ from his 1980 gospel album Saved.

Recorded at the legendary Fame Studios in Muscle Shoals, AL at the height of his Christian conversion, the song sees an impassioned Dylan seek to find an appropriate way to repay the Lord for his newfound salvation. His vocals convey the true sincerity of his prayers and his convictions, but when even words aren’t enough to get the extent of his feelings over, he moves to the harmonica to take up the cry. What follows are two of the purest and most emotional solos on any instrument that you will hear on any recording and any album. Dylan’s harmonica becomes an extension of his soul, of his spirit and of his faith, and in this instance, tell the story in his song even better than his words can. You may not believe in a higher power, but when you hear Dylan blowing those aching and yearning final notes on the harmonica here, you can take it as gospel that he never played the harmonica better.

‘To Fall in Love With You’ (1986)

While songs like ‘Up To Me’, ‘Blind Willie McTell’ or ‘Red River Shore’ would feel finished by anyone else’s standards and would be worthy inclusions on any album, some of Dylan’s best-lost songs never even got finished.

In the 1960s, there was ‘Love is Just a Four Letter Word’, ‘She’s Your Lover Now’, ‘I Can’t Leave Her Behind’ and ‘I’m Not There’. Songs that fell by the wayside and into the dust of history. Twenty years later, in 1986, Dylan started and failed to finish another great lost song, ‘To Fall in Love With You’.

Just like the exemplary ‘I’m Not There’ before it, the lyrics are far from complete, and Dylan, for the most part, is singing a dummy vocal, and yet the result is both captivating and beguiling. You can’t take your attention away for a second. The words might not be completely in place, the story might not be finished, and the phrasing might be loose, but the feel is captured entirely. The mood and atmosphere are enchanting, and though Dylan is famed for his lyrics, even winning the Nobel Prize for them, it’s actually the feel, the mood and the aura of his performance which is the most important thing to his music.

‘Brownsville Girl’ (1986)

Not just the best song on Dylan’s 1986 album Knocked Out Loaded, this song has to be in the conversation for his best song from any album.

A sprawling, gargantuan epic, this song is a modern Western based loosely on Dylan’s foggy recollection of the 1950 Gregory Peck picture The Gunfighter. Dylan distils the entirety of that (fantastic) film into a few short verses and takes off into telling not only his own story but the story of all of America and the fading of the true Golden Age of the country.

Clocking in at a little over eleven minutes, the song is constantly expanding and yet feels like it could or should last for even longer. Dylan’s vocals are breathless and rapid-fire at times or slow-burning and easygoing at others.

The whole world is here inside this song; there are pearls of wisdom (“You always said people don’t do what they believe in, they just do what’s most convenient and then they repent”) and there are hilarious quips (“and I always said ‘hang on to me, baby, and lets hope that the roof stays on”). There is love (“I feel pretty good, but that ain’t saying much, I could feel a whole lot better if you were just here by my side to show me how”) and there is betrayal (“I know she ain’t you, but shes here and she’s got that dark rhythm in her soul”). There’s life (“Turn him loose, let him go, let him say he outdrew me fair and square”) and there is death (“I want him to feel what it’s like to every moment face his death”). There is the mundane (“even the swap meets out here are getting pretty corrupt”) and the profound (“oh, if there’s an original thought out there, I could use one right now”) at the end of it all, Dylan is no longer sure whether he is watching a Gregory Peck or if hes in one. It all seems like it was happening such a long time ago, anyway, long before the stars were torn down.

This one song has more great lines and lyrics than most people can manage in a lifetime, but that isn’t even the best thing about it. With its ragged rhythm, percolating organ, brass motifs and acoustic embellishments, the story is sold by both Dylan and his wonderful backing singers. Whilst plenty of people question his vocal abilities, his exemplary phrasing is undeniable here and his voice becomes increasingly impassioned with each and every line. Behind him, the Queens of Rhythm take their turn as a cinematic Greek-chorus, and begin to sell each image and emotion with their howls and roars and oohs and ahhs.

No one else could write this song—no one else would dare—and no one else could do it justice as well as this, even if they had. And, even if, somehow, someone else had managed to pull a song of this magnitude and quality out of the bag, they wouldn’t then be as perverse as to bury it in the second half of one of their worst albums, but, in true Dylan fashion, that’s exactly what he did.

And that’s what makes him so great.