‘Under the Red Sky’ (1990)

Following his comeback album Oh Mercy, 1990’s Under the Red Sky was dismissed at the time as being a lightweight album, dashing the hopes of anyone who hoped that Dylan was back to his best, but ignore the dissenters, there are some fantastic songs on the record, not least of all the title track.

Appropriately so, considering the fairy tale at the heart of the song, what sounds bright and positive enough at first turns out to be a dark and treacherous story full of destruction and plunder. With gorgeous piano floating through the song, a hazy accordion, and a memorable slide-guitar part supplied by George Harrison, Dylan’s creaking and ageing voice beautifully contrasts with the band and informs the hidden darkness in his words.

‘Handy Dandy’ (1990)

25 years later, after recording ‘Like a Rolling Stone’ together, Bob Dylan brought Al Kooper back to the studio to supply organ parts to the effervescent ‘Handy Dandy’. Elsewhere on the track, Waddy Wachtel and Jimmie Vaughan trade lightning licks on the guitar while Dylan delivers a riveting vocal performance.

While so much discussion on Dylan’s voice, especially during this time period, focuses on his tone, it’s his phrasing and delivery which really astonish here. He is a master at fitting an unlikely amount of syllables into a bar, and this is one of his most impressive such performances. The song bounds along at a riotous pace already and feels even quicker thanks to the breathless machine-gun-like delivery from Dylan as the images pile up. ‘Handy Dandy’ might musically sound like a modern-day ‘Like a Rolling Stone’, but Dylan had to dig into his ‘Subterranean Homesick Blues’ singing style to fit all these words in.

‘Lone Pilgrim’ (1993)

You could really pick any number of Dylan’s solo acoustic recordings from 1992s Good as I Been to You album, or its 1993 follow up World Gone Wrong, to highlight, such as ‘Frankie & Albert’, ‘Hard Times’, ‘Tomorrow Night’, ‘You’re Gonna Quit Me’, ‘You Belong to Me’, ‘Blood in My Eyes’ and ‘Love Henry’, ‘ but ‘Lone Pilgrim’ may just be the most devastating of the lot.

The song dates back to the early 1800s, and although the author is unknown, it has occasionally been credited to both Elder John Ellis and B F White over the years. In his version, Dylan sounds like he’s even older than the song itself. Singing at peace from beyond the grave, he whispers the lyrics at times, and at others, he sounds like an echo caught in the wind while his guitar delicately ripples around the words. Haunting doesn’t even begin to cover it.

‘Miss the Mississippi And You’ (1992)

Before he decided to record two solo albums of traditional folk, blues and spirituals at his home studio, Dylan had intended to record such songs with the backing of David Bromberg and a small, intimate band. Bromberg and Dylan had first recorded together twenty years earlier, and now the old friends came together again to tackle songs such as ‘Hey Joe’, ‘Catskills Serenade’ and ‘The Lady Came from Baltimore’.

At the sessions, they got down an electrifying version of ‘Duncan and Brady’, which wouldn’t have been out of place on Dylan’s 2001 masterpiece Love and Theft, and a gorgeous rendition of the Jimmie Rodgers song Miss the Mississippi and You. Though the sessions were ultimately scrapped, they have been widely bootlegged, and it wouldn’t be the last time Dylan that returned to Rodgers in the 1990s, as he also recorded a version of the 1930 song ‘My Blue-Eyed Jane’ with Emmylou Harris in 1997.

‘Highlands’ (1997)

So many of Dylan’s best albums close with great long songs. ‘Desolation Row’ sees out Highway 61 Revisited, while Blonde on Blonde ends with the thin wild-mercury of ‘Sad Eyed Lady of the Lowlands’. More recently, Dylan’s opus Rough and Rowdy Ways ends with the truly epic ‘Murder Most Foul’, so it was only fitting that the album where he reinvented himself and truly became the artist he was always destined to be, Time Out of Mind, ended on a similarly lengthy song, as well.

A meandering slow-burn ballad, the narrative weaves in and out of Dylan’s stream of consciousness, drifting from scene to scene and blowing through the wild and honeysuckle-sweet air of the Scottish Highlands or else the streets of Boston town. In fact, the most memorable scene in the song takes place in a Boston restaurant where Dylan recounts a hilarious interaction between himself, the waitress who’s serving him and the sketchpad and literature that bring the pair together (or pushes them apart).

‘Born in Time’ (1990)

Originally written for Oh Mercy but ultimately left off the album, Dylan returned to ‘Born in Time’ during the sessions for his 1990 follow-up. One of the most beguiling tracks on Under the Red Sky, the song is the emotional anchor and grounding point of the record.

A tragic, turbulent, and resigned romance, the song is full of remorse, experience, and acceptance. Though the rest of the album heavily features fairy-tale imagery and childlike expressions—indeed, the album is even dedicated to Dylan’s then infant child Desiree, and many have seen it as an album he made for her to enjoy—this song is a mature, poetic look at love and the price we pay to keep hold of it.

‘Standing in the Doorway’ (1997)

If Dylan had started the decade with his then-most mature lyrics, he would have seen it out with his most mature album. Time Out of Mind is full of reverence, wisdom and the lessons learned from a life of hard living. It’s an album about having lived, and lived well, but as much as anything, it’s also an album about being close to the end.

None of the songs on the record set the scene or tell the tale quite as clearly as ‘Standing in the Doorway’. There is a celestial quality to the way this song rolls into the horizon, rolls across your consciousness and lingers in your mind. It makes you feel like you’ve been listening to it your whole life. It makes you feel like you’ve become untethered from time and have gotten lost out there among the stars. “Don’t know if I saw you if I would kiss you or kill you. It probably wouldn’t matter to you anyhow,” Dylan sings at one point, and “last night I danced with a stranger, but she just reminded me you were the one” at another. Most people don’t write lines that good in their entire careers, but here, Dylan makes it all seem as natural as rain.

‘The Times We’ve Known’ (1998)

It wasn’t just in the studio where Dylan turned to other people’s songs for inspiration in the 1990s. Alongside his two officially released cover albums and the one he scrapped, Dylan also played plenty of songs written by other writers on stage during the decade.

Among the very best were a sumptuous performance of Gordon Lightfoot’s ‘I’m Not Supposed to Care’ as well as excellent readings of Elizabeth Cotton’s ‘Shake Sugaree’ and Blind Boy Fuller’s ‘Weeping Willow’. Perhaps his best cover of the decade, though, and maybe one of his greatest covers ever, was his version of the Charles Aznavour song ‘Les Bon Moments’, based on the English translation by Herbert Kretzmer, re-titled ‘The Times We’ve Known’.

“I usually play these things all to myself” he said before starting, “but, I feel like I’m all by myself now”.

‘Red River Shore’ (1996)

Dylan is famous for leaving his best songs off his albums, and Time Out of Mind was no exception. ‘Red River Shore’ sounds like the kind of song that has been around for all time, that has been passed down on the wind and through the years. It sounds like the sort of thing that Dylan was covering so often back then, but such is his genius at tapping into an age-old feeling and an age-old tradition, this one is all his own.

An aching, yearning and beautiful ballad, the whole world begins and ends in the almost eight minutes it takes Dylan to tell this tale. “Some of us turn off the lights and we lay in the moonlight shooting by. Some of us scare ourselves to death in the dark to be where the angels fly”, Dylan laments at the start of the song, and goes on to tell a story true to life of love found, and love lost. A story of jilted love. “I knew when I first laid eyes on her, I could never be free,” he sings, and you’ll feel the same way the first time you lay your ears on this beautiful song.

‘Not Dark Yet’ (1997)

When Dylan was awarded the Nobel Prize for Literature in 2016, most of the focus in the fallout of the decision was turned on and tuned into his revolutionary 1960s work. Many rehashed the story of his life, culminating in his legendary motorbike crash in 1966 which closed up the book on the first chapter of his career as if the next fifty years had never happened.

Much less attention was being paid to Dylan in the mid-1990s, but when he was struck down by a case of pericarditis, brought on by a prior histoplasmosis infection, Dylan was rushed to the hospital, his tour dates all cancelled, and he was later quoted as saying that “I really thought I’d be seeing Elvis soon”. He’d been singing about death and darkness for his whole career, but he’d never come closer to meeting his end than he had in 1997.

Though much of his new album had already been written and recorded by the time he was admitted to the medical facility, his brush with death highlighted just how morbid and dark his new album was when it arrived and retrospectively infused his vocal delivery with so much weight and so much additional force. The record is littered with the lives of his past, haunted by the spectre of death and shrouded in dullness and decay at every turn.

“It’s not dark yet, but it’s getting there” is a lyric for our time. In an age when misinformation abounds, fascism is on the march, the climate becomes ever more unstable, and the richest people on the planet are instigating the biggest and most un-just transfer of wealth from the poorest among us, each and every day gets darker, but there is still hope that we can change course, resist and turn things around. We can still fight for progress and prosperity. Things may be dark, but the lights haven’t gone out entirely yet and, just like Dylan sings in the song, “behind every beautiful thing, there’s been some kind of pain”.