Bob Dylan may well be one of the most covered artists in modern music, his unique style conversely providing itself as the perfect blank canvas for many artists. However, that hasn’t encouraged him to do too much of his own covering over the years. While he may have started as any folk singer would, by covering the American standards, he neglected to lend his voice to another singer’s words for a long time after finding his own pen. After all, he was being branded as “the voice of a generation” so one would assume a certain amount of ego develops. But soon enough, the covers began creeping back in.
On the occasions that he did pick up another artist’s work for his own use, Dylan, ever the mercurial performer, took them to only places the freewheelin’ Bob Dylan possibly could. While some songs found their way on to his live set or featured in Self Portrait, Dylan, all of them have the same tonal richness and complexity, which makes a great Bob Dylan track. It’s the sign of a great artist, that, no matter the context, he can create something in his own image.
Some of the songs shared here are listed not for the note-perfect performance or the expert ear used to find the choicest cuts, but for the feeling and sentiment that Dylan and his history bring to the recording. It’s something we can see most clearly in the various live and impromptu performances which litter this list. While Dylan would eventually begin adding in covers to his studio releases once more, we’ve chosen to largely stay away from the standards that he has bookended his career with.
The list may be an irreverent look back at Dylan’s favoured tunes but it also provides a short and sharp reminder of the kind of undeniable talent he possesses. Utterly unique in every way, simply put; Dylan makes these songs his own.
With a host of stellar names on the list, each one likely blessed to have the pleasure of a Bob Dylan version of their song, it makes for a crystalline reason as to why Bob Dylan is still so revered to this day — he is 100% unique in every way.
Bob Dylan’s 10 best covers:
10. ‘Brown Sugar’ – The Rolling Stones
Sharing a tour with The Rolling Stones is always a nerve-racking thing to do. For Bob Dylan, an artist who has flourished within the intimacy of smaller venues and was approaching the new century with a depleted following, it was a lot of pressure—but he stepped up and delivered an impeccable set.
Perhaps as a mark of his confidence, six songs into his set during the Stones’ Seattle show in 2002, he took on the band’s controversial hit ‘Brown Sugar’. It’s a big song to attach oneself to, especially considering the environment.
“The Rolling Stones are truly the greatest rock and roll band in the world and always will be,” Dylan once famously said of his contemporaries. “The last too. Everything that came after them, metal, rap, punk, new wave, pop-rock, you name it… you can trace it all back to the Rolling Stones. They were the first and the last and no one’s ever done it better.”
9. ‘Not Fade Away’ – Buddy Holly
A lot of artists have taken on Buddy Holly’s rock ‘n’ roll standard during their time, including the aforementioned Rolling Stones. But Dylan’s version adds a certain unquantifiable integrity to proceedings. The performance feels like Dylan is supremely and intrinsically attached to the song forevermore.
Whether it was witnessing the Rolling Stones perform the track or indeed his love of Buddy Holly which pushed him towards the song is unknown but we do know it was a track he frequently played with The Grateful Dead during his time on tour with the group.
It’s a classic song that only reaches higher with Dylan at the helm.
8. ‘Learning To Fly’ – Tom Petty
Performing shortly after learning of his friend, Tom Petty’s tragic death, Bob Dylan paid tribute to the man who arguably rescued his career in the eighties with a fitting cover of ‘Learning To Fly’.
“It’s shocking, crushing news,” he said. “I thought the world of Tom. He was a great performer, full of the light, a friend, and I’ll never forget him.” Dylan and Petty played together in the rock supergroup that also featured Roy Orbison and George Harrison.
As well as the Wilburys, Petty also invited Dylan to join his tour during the eighties and likely rescued his career or, at the very least, Petty re-instilled Dylan’s passion for performance. Watch the heart-wrenching performance below.
7. ‘The Boxer’ – Simon & Garfunkel
One of the most bizarre Bob Dylan albums of all time sees the singer in his most unreachable moments, providing covers of American standards and reflecting on his own work too. The album is largely regarded as a failure but this one gem on the record is worth remembering.
Dylan’s desire to add a level of extra gravity to Simon & Garfunkel’s classic ‘The Boxer’ can be heard from the first minutes and the troubadour achieves his goal with relative ease.
Dylan would later share a show with Paul Simon where he joined in on a duet of ‘Sound of Silence’ for some lucky fans. Listen to his cut of ‘The Boxer’ below and be reminded of just how much command and attention Dylan demands when performing.
6. ‘Young At Heart’ – Frank Sinatra
A few years ago one word was thrown at Dylan more than any other; ‘crooner’.
The moniker was slung at him mainly because of this one cover and his perceived new style. A Frank Sinatra stalwart, Dylan put on his figurative suit and tie, tipped his hat and found himself atop a stool with a cold cocktail and a cigarette billowing beautiful blue smoke.
He gives the track another slice of authenticity, clearly offering the title’s proposition and being young at heart. Dylan sings the song with a sentiment and unabashed joy that separates the track from most of his other work. There’s no doubt that this is one of the more unusual covers in Dylan’s repertoire, nevertheless, he manages to make it his own.
5. ‘House of the Rising Sun’ – The Animals
The traditional blues song is given a fresh lick of paint by the young folk singer and he takes the track to some interesting new spaces.
One thing Bob Dylan can always be given credit for is his honesty. Whether it’s honesty about his work, about others or about both of the two combined, Dylan tells it like it is. He was equally honest about his 1962 release of ‘House of the Rising Sun’ later saying that it paled in comparison to the more-well-known version by The Animals.
Although Dylan’s rendition does possess a little more folky twang alongside a more vintage and gritty sound, it’s hard to argue with the man himself—but it still ranks as one hell of a cover and offers Dylan up as an expert interpreter.
4. ‘Big Yellow Taxi’ – Joni Mitchell
One of the more covered songs in our list, it’s hard to imagine anybody as succinctly summing up the entire counter-culture movement, than Joni Mitchell singing ‘Big Yellow Taxi’. To hear other people singing the song usually means to deal with a terrible karaoke version.
However strange it may be to hear this iconic tune without Mitchell’s effortless vocal performance, it feels just as joyous to hear Bob Dylan doing his best to sing one of the most famous songs of the sixties. Often seen as an outtake from Self-Portrait, the Dylan record that was essentially a collection of covers put together by his record company without his permission, the track is still wholesome, charming and charismatic enough to put a smile on our face.
The two writers would naturally share the same space during their careers and have sometimes fallen foul of one another. Mitchell even once wrote a song about the “miserly” figure of Bob Dylan, the one she endured during the Rolling Thunder Revue tour.
3. ‘People Puttin’ People Down’ – John Prine
Following his death, it would appear the wider world suddenly woke up to the incredible songwriter John Prine. Dylan, however, has consistently cited the songwriter as an influence and one of his favourites.
“Prine’s stuff is pure Proustian existentialism,” Dylan once told MTV producer Bill Flanagan. “Midwestern mindtrips to the nth degree. And he writes beautiful songs. I remember when Kris Kristofferson first brought him on the scene. All that stuff about Sam Stone the soldier junky daddy and Donald and Lydia, where people make love from ten miles away.
“Nobody but Prine could write like that. If I had to pick one song of his, it might be Lake Marie.”
Not only did Dylan speak about Prine, but he also covered his track ‘People Puttin’ People Down’ in 1991 whilst performing on the Rome date of his European tour and the result is pure magnificence.
2. ‘Something’ – The Beatles
Arguably one of George Harrison’s finest compositions, the Abbey Road track is regarded as one of the greatest love songs ever written—even Frank Sinatra thought so. That said, Bob Dylan’s cover of the track is so much weightier in emotion than The Beatles could ever sound on record.
On one rare occasion when Dylan did cover The Beatles, it carried a heavy emotional sentiment. “He was such a good buddy of mine,” Dylan said while on stage at Madison Square Garden on November 13, 2002, almost one year to the day that Beatles guitarist George Harrison passed away.
Moments later, Dylan would roll into a heartbreaking rendition of ‘Something’.
If you needed proof of how affecting that relationship was then you need only look at the footage below which sees Bob Dylan sharing a touching cover of The Beatles’ ‘Something’ in tribute to his friend, George Harrison.
1. ‘Hallelujah’ – Leonard Cohen
Two of modern music’s finest songwriters of all time met in curious circumstances. Cohen was in Paris at the same time Dylan was performing a headline show and had arranged to meet him backstage where a typically quizzical Dylan was particularly interested in Cohen’s hit song ‘Hallelujah’.
“How long did it take to write it?” Dylan asked. “Two years,” Cohen lied knowing full well that the process of forming that particular song actually stretched into five years. In response, Cohen told Dylan: “I really like ‘I and I,” in reference to the song that appeared on Dylan’s album Infidels. “How long did it take you to write that?” Cohen then asked. “About fifteen minutes,” Dylan replied.
However, long it took to write, one thing is for sure, ‘Hallelujah’ is one of the greatest songs ever written and Dylan was more than happy to take on the track for an audience in 1988. While Jeff Buckley’s definitive version of the song was yet to come, Dylan’s retelling of the fabled story is a fantastic rendition.
“That song ‘Hallelujah’ has resonance for me,” Dylan later told the New Yorker. “It’s a beautifully constructed melody that steps up, evolves, and slips back, all in quick time. But this song has a connective chorus, which when it comes in has a power all of its own. The ‘secret chord’ and the point-blank I-know-you-better-than-you-know-yourself aspect of the song has plenty of resonance for me.”