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From Johnny Cash to George Harrison: Bob Dylan’s 10 best duets

When you quickly become the voice of a generation as Bob Dylan did in the sixties with a fresh look at pop music, there’s a tendency to keep other artists and collaborators far from your sound. The same cannot be said for Bob Dylan, however, who has always welcomed the artistry of another to share the stage and the mic with him over his long career.

Whether it was in the studio or out on stage, it was clear that Dylan loved to collaborate with those he deemed worthy of his time. Whether it was because the singer had spent so much time working on his own, without the aid of a real band or bandmates, or because he truly admired those he worked with, Dylan has always championed collaborative creativity. Below, we’ve collected ten of our favourite Bob Dylan duets as proof.

Bob Dylan has never been one for absolute perfection. His is a style that requires heart and emotion over note-perfect performance. It’s an attribute that lends itself to collaboration more easily than say the imposing work of Led Zeppelin or even Joni Mitchell (more on her later), who were more focused on achieving the top performance whenever they could. As such, Dylan has found some incredible artists to perform with over the years.

As Dylan welcomes his collaborators with a warm embrace and a confidence that there is no wrong way to play his songs, it allows for those collaborators to express themselves more fully and, dare we say it, enjoy themselves too. While below are some of the biggest names in the music world, for a brief moment working with Bob Dylan they were just friends and fans of the freewheeling troubadour.

Bob Dylan’s 10 best duets:

‘Girl From North Country’ – Johnny Cash & Bob Dylan

Bob Dylan first recorded his song ‘The Girl From North County’ back in 1963 but when he was invited on to the Johnny Cash Show six years later there was only one song they would sing together. Dylan had remained close friends with Cash since they first met at Newport Folk Festival in 1964, a bond that remained strong up until Cash’s death in 2003.

There was a great deal of mutual respect between the two icons with Cash recalling in Cash: The Autobiography: “I had a portable record player that I’d take along on the road, and I’d put on [The] Freewheelin’ [Bob Dylan] backstage, then go out and do my show, then listen again as soon as I came off. After a while at that, I wrote Bob a letter telling him how much of a fan I was. He wrote back almost immediately, saying he’d been following my music since ‘I Walk the Line,’ and so we began a correspondence.”

“In plain terms, Cash was and is the North Star; you could guide your ship by him—the greatest of the greats then and now,” Dylan wrote upon Cash’s passing in 2003. “Truly he is what the land and country is all about, the heart and soul of it personified and what it means to be here; and he said it all in plain English. I think we can have recollections of him, but we can’t define him any more than we can define a fountain of truth, light and beauty.”

There’s perhaps no better example of their mutual appreciation for one another than in their touching duet below.

‘If Not For You’ – George Harrison & Bob Dylan

Bob Dylan shared a tumultuous relationship with The Beatles. Inspiring and then becoming infuriated with John Lennon was one facet but the friendship he shared with George Harrison will remain his lasting legacy with the Fab Four. Perhaps the greatest showing of that was at the Concert for Bangladesh.

The benefit for the people of Bangladesh who had been ripped apart by famine and war was a rare showing for Dylan at the time and was proof of his commitment to Harrison as a friend. While their on stage performance was a powerful moment it is their rehearsal rendition of ‘If Not For You’ which bears the most beauty.

To ask all his musician friends to come and jam was the least Harrison could do. While both Paul McCartney and John Lennon turned down the offer following The Beatles’ less than harmonious split, Dylan got over his own reclusive tendencies and took to the stage for the first time since his iconic 1969 performance at the inaugural Isle of Wight Festival.

This is what makes the clip so touching. While Dylan is obviously a consummate performer, in the footage there is a sense of care that Harrison affords his friend, Dylan. A few subtle glances, some shared moments and some body language cues show that their relationship went on far beyond their musical inclinations.

‘Forever Young’ – Bruce Springsteen & Bob Dylan

There are a collection of serious performers on this list, the kind of artists who can fill stadiums and sell millions of records without too much trouble. One of those performers is The Boss, Bruce Springsteen. One of America’s greatest songwriters is, however, reduced to being a simple fan when he takes the stage with his idol Bob Dylan to perform ‘Forever Young’. First appearing on 1973 record Planet Waves, the track only really picked up steam when The Band covered it, except, of course, if you were a devoted fan like Springsteen.

That is certainly the most beautiful part of this duet captured in 1995 at Rock Hall, Springsteen acts, for all intents and purposes, like a fan who has picked up a guitar and managed to fool security into letting him play with his hero. A talented fan, maybe—but a fan nevertheless. Springsteen’s performance is practised and perfected and even provides some guide ropes for Dylan himself. What makes this doubly brilliant is the fact it’s clear Dylan holds just as much respect for his contemporary on the stage. Dylan leans into the duet and may even crack a smile or two while performing.

So, while below there’s some rarely seen footage of Bob Dylan and Bruce Springsteen performing together, two icons of their day, it could quite easily be the ramshackle jam of two friends in the bar, banging their empty glasses for a beat and singing their hearts out.

‘Coyote’ – Joni Mitchell & Bob Dylan

Working in similar circles throughout most of their life, Joni Mitchell and Bob Dylan share a fractious relationship. Mitchell once famously labelled the singer a “plagiarist” while Dylan has often been dismissive of Mitchell too. While many people put this down to competitiveness a lot of their issues stem from witnessing each other’s methods during the Rolling Thunder Revue’.

Joni Mitchell joined the incredible roster of Bob Dylan, Joan Baez, Roger McGuinn, T-Bone Burnett, Ronee Blakely and others to take part in a historic travelling roadshow. One beautiful highlight. however, did see Mitchell and Dylan share the camera and the makeshift stage to perform Joni’s newly written song ‘Coyote’ for a truly memorable moment.

The performance is a crystalline look at two of the world’s most prominent folk singers. It was captured by Dylan’s team when working on Renaldo & Clara but was recently and expertly compiled and cut by legendary Martin Scorsese as Rolling Thunder Revue: A Bob Dylan Story and released to the wilds of Netflix in 2019.

The track, having only recently been conceived by Mitchell, would go on to open Mitchell’s 1976 album Hejira but was in the early workings while Mitchell was on the tour. Sitting in Gordon Lightfoot’s house Mitchell is fearless in performing the new song in front of a host of incredible folk artists, seemingly assured in her work. While the term ‘duet’ may be a loose one in this respect, it is a shared performance which has us dreaming of what could have been.

‘Don’t Think Twice It’s Alright’ – Eric Clapton & Bob Dylan

During the recording of Eric Clapton’s No Reason to Cry the singer welcomed countless artists to contribute. With The Band, Levon Helm, Van Morrison, Rick Danko, Billy Preston, Marcy Levy and countless others settling in the studio, it would be the surprise addition of the great Bob Dylan which is remembered most fondly about the star-studded meeting of minds.

“Dylan dropped by and was just hanging out, living in a tent at the bottom of the garden,” Clapton would later say in reflection. “He would sneak into the studio to see what was going on,” he added. In fact, rumour has it that Dylan even offered his latest unrecorded song ‘Seven Days’ to Clapton who, after some consideration, passed on the opportunity and allowed Ron Wood to take the lead.

But in the meantime, what Dylan and Clapton did work on was a cover of Dylan’s song ‘Don’t Think Twice It’s Alright’ as part of his legendary birthday party sessions.

‘Gates of Eden’ – Neil Young & Bob Dylan

Neil Young and Bob Dylan have been friends for a long time and any moment they share on stage is a great one. But this performance of ‘Gates of Eden’ os particularly brilliant. When Dylan kicked off his ‘Never Ending Tour’ in 1988, Young stepped forward and arrived on the stage of California’s Concord Pavilion to perform a very special rendition of the track.

Young, whose home is in touching distance of the venue, rocked up and delivered a rousing contribution to the song. “Neil drove up in his Cadillac convertible,” Richard Fernandez, the tour manager told Young biographer Jimmy McDonough: “His Silvertone amp in the back,” he added. “Was Young ever intimidated to be joining one of his heroes on stage?” McDonough asked, to which David Briggs replied: “I’ve never seen him be intimidated by anyone musically.”

“Neil took over the whole show,” his manager Elliot Roberts recalled before Young came bouncing over to Dylan: “Great show! See ya tomorrow night, Bob,” he said to which Dylan casually replied, “Yeah, Neil,” with almost exhausted acceptance.

The song that duo took on, originally appearing on Dylan’s fifth studio album Bringing It All Back Home, was released in 1965 through Columbia Records and featured as the B-side to the now-iconic ‘Like a Rolling Stone’. According to Oliver Trager, the author of the encyclopedic sourcebook detailing many of Dylan’s songs, ‘Gates of Eden’ arrived as Dylan’s declaration that “blind belief in a forgiving afterlife is the ultimate lie because it creates complacency in this one.”

“That’s Neil Young on the guitar,” Dylan said. “Give him a hand!”

‘Dark Eyes’ – Patti Smith & Bob Dylan

20 years prior to the below duet, in 1975, Patti Smith wasn’t quite the literary behemoth she would become. But one person knew talent when he saw it in the smoky coffeehouses of New York’s underground scene, and that person just happened to be Bob Dylan.

Dylan and Smith would form a friendship over a mutual love of poetry and music that continues to this day. One pinnacle moment of their relationship coming in 1995 with the duet of Dylan’s rarely heard song. While Smith would make a hash of their first meeting, she would form an unstoppable friendship with the freewheelin’ Dylan.

The song in question ‘Dark Eyes’, was originally recorded in 1985 and released on Dylan’s album Empire Burlesque, offered the pair the chance to come together over a few nights in new york some 20 years after that lasting first meeting.

Patti Smith supported Dylan on the Paradise Lost Tour, with Bob always offering the singer his utmost respect, it seemed fitting that he performed this song as a duet with her. He said, “a lot of girls have started since Patti’s started, but Patti’s still the best.” It’s hard to disagree.

‘I Shall Be Released’ – Elvis Costello & Bob Dylan

During the mid-1990s, Bob Dylan was quietly going about his business as the never-ending troubadour he is. Press attention on the star was largely dwindling but while the public were preoccupied with other singers, artists from across the music world still knew of Dylan’s mercurial majesty. One such artist was Elvis Costello who, when asked, jumped at the chance to share the stage with Bob Dylan. That invitation arrived in 1995 for a very special duet of ‘I Shall Be Released’.

One of Dylan’s most poignant tracks, ‘I Shall Be Released’ has been covered by numerous singers but this has to be one of the finest performances. The new wave icon joins the folk God for and they let rip on one of rock music’s greatest.

By the time of this tour, Dylan had been playing live for eight solid years, a simply mammoth time on the road that is unlikely to ever be repeated in the modern age. But while Dylan’s touring was not newsworthy enough to gather widespread press attention, the singer was giving his audiences some of the best value performances they had enjoyed in decades. As well as providing the reem of greatest hits he had accrued he also came complete with big duets too, Costello’s inclusion on this version of ‘I Shall Be Released’ at Brixton Academy is simply magnetic.

‘Sound of Silence’ – Paul Simon & Bob Dylan

Paul Simon may have become used to sharing the stage with another man for many years before he and Dylan toured together in 1999. After all, it was his work as part of Simon & Garfunkel that had largely offered him the chance to take the stage at all—but still, this moment must rank as a special one for all in attendance.

Dylan and his lo-fi performance is a natural fit for Simon. The freewheelin’ Bob Dylan had softened somewhat in his old age and was no longer determined to dominate the stage as before. Now, he was keen that his legacy of some of the best live performances ever known continued in whatever guise those performances could. With that mind, he was always happy to sometimes play second fiddle to the somewhat showier Paul Simon.

Shortly before the tour, Dylan and Simon got together at the latter’s New York apartment with a couple of acoustic guitars and began to strum their way into a setlist. We can only imagine the scene of two of modern music’s finest songwriters pawing over their work together.

It must’ve been a fruitful evening of swapping stories and teaching one another songs, “I consider him one of the preeminent songwriters of our time,” Dylan told USA Today before the tour began. “Every song he does has got a vitality you don’t find everywhere.” It’s perhaps one of the reasons the duo chose to share a duet each night, sometimes choosing ‘Knockin on Heaven’s Door’ and sometimes Simon’s classic ‘Sound of Silence.’ Below you can hear the latter land with aplomb.

‘Knockin on Heaven’s Door’ – Tom Petty & Bob Dylan

By the mid-eighties, Bob Dylan was struggling to draw the crowds as he once had. Dylan had been largely replaced by a new set of classic rock stalwarts. Including Tom Petty.

Petty and the Heartbreakers may well have been the main draw of the 1986 True Confessions tour but the singer and his band made sure that they gave ample room to two stunning artists they brought along with them for the ride: one Stevie Nicks and the other Bob Dylan.

For Dylan, the chance to go out on the road and once again find his feet on the stage was an opportunity he couldn’t afford to pass up. Dylan was eternally grateful for the inclusion on the tour, “Tom was at the top of his game and I was at the bottom of mine,” he wrote in his 2004 book Chronicles.

As noted in the 2005 Paul Zollo book Conversations With Tom Petty, however, the singer felt differently to Dylan: “There was never a night when the audiences weren’t incredibly ecstatic about the whole thing,” he said. One such ecstatic moment came at the end of the evening when Petty would join Dylan for a performance of the latter’s classic ‘Knockin’ On Heaven’s Door’. It’s a touching performance not only between two incredible performers but between two friends too.

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