An Introduction To Bob Dylan In 10 Songs

Bob Dylan and The Byrds
Bob Dylan and The Byrds | © The World Famous Comedy Store/Flickr
Clémence Charbonnier

Neil Young called him “the master,” and he was right. Bob Dylan certainly is one of the greatest and most influential singer-songwriters of our time. He is among the most frequently covered singers of the past 100 years, David Bowie wrote a song for him, and the list of accolades goes on. Culture Trip invites you to rediscover this giant figure of modern music through 10 of his best songs, from the classics to some of his lesser-known gems.

‘Song to Woody’

When he first arrived in New York City, Robert Zimmerman was 19 and had never written any songs of his own. The nights he spent performing at the Café Wha? were filled with cover songs from America’s greatest folk composers, and it is no secret that young Dylan’s absolute favorite was Woody Guthrie. ‘Song to Woody’ is, in Dylan’s own words, ‘the first song [he] wrote of any substantial importance’ and was dedicated to him. Behind every word, quite clearly, lies a young man’s yearning to embrace the same kind of life as Guthrie. It is a youthful masterpiece.

Further reading: Bob Dylan’s Last Thoughts On Woody Guthrie

‘Blowin’ in the Wind’

‘Blowin’ in the Wind’ was first sung by the band Peter, Paul and Mary in 1962 and recorded by Dylan in 1963 for the album The Freewheelin’ Bob Dylan. It became a hymn for the fight for civil rights and remains one of Dylan’s most iconic songs. Along with several other tracks from the album, it led him to be considered as a speaker of a generation and a voice against war – although this role was never one he intended to play. Years later, he would do everything in his power to change his reputation and rid himself of this burden.

Further Listens: Talking World War III Blues, Masters of War, The Times They Are A-Changin’, Only a Pawn in Their Game

‘Boots of Spanish Leather’

In ‘Boots of Spanish Leather,’ which you can find on The Times They Are A-Changin’ album, Dylan wrote of fading love. Refusing a gift from his absent lover as she is away in Europe, the singer eventually accepts one as soon as it becomes clear to him that she will never come back to him. He ironically agrees to replace his former everlasting love with a pair of Spanish boots with which to walk away. Dylan here mixes sensibility, love and beauty with disdain and rejection – classic of him.

Further Listen: Don’t Think Twice, It’s All Right, Most Likely You Go Your Way (And I’ll Go Mine)

‘Mama, You Been On My Mind’

Many Dylan songs were first abandoned then fortunately saved from oblivion by The Bootleg Series albums, featuring rare and un-released tracks. ‘Mama, You Been On My Mind’ is one of those hidden gems. Although it was cut out from Another Side of Bob Dylan, it found its way to The Bootleg Series Volumes 1–3 and, thus, got officially released for the first time in 1991. The song has something special in its lyrics; something about them make it one of the finest and most tender love songs ever written by its author. A few years later, it was perhaps even more gracefully interpreted by Jeff Buckley.

‘Subterranean Homesick Blues’

‘Subterranean Homesick Blues’ was famously recorded in a single take and featured in Bringing It all Back Home. With this album, Dylan’s music electrified itself, and while many fans were left shocked and feeling betrayed by the change of musical direction of their idol, ‘the master’ was proud to introduce folk-rock to the world. When the song was released, Dylan also revealed what is now widely thought to be the first notable music video of our history.

Further Listen: Maggie’s Farm

‘Mr Tambourine Man’

‘Mr Tambourine Man’ is also to be found on Bringing It All Back Home. The origins of it have been blurred through time: while Dylan once said the idea of it came to him as he was watching Federico Fellini’s La Strada, some recognize the influence of French poet Arthur Rimbaud in its mystical lyrics or believe the songwriter actually found inspiration for this song in New Orleans’ Mardi Gras. Wherever it comes from, ‘Mr Tambourine Man’ is definitely one of the most mysterious and irresistible Bob Dylan songs. Surprisingly, opening the song with its chorus (which is rather rare in popular music) and through his words and music alone, Dylan takes us on a trip upon his magic swirling ship.

‘Like a Rolling Stone’

Just a few months after Bringing It All Back Home was a hurricane among his fans, Bob Dylan released the electric Highway 61 Revisited and made the six-minute-long ‘Like a Rolling Stone,’ the longest of all his singles. The song was a hit, and the whole world fell for its rocky rhythm and acerb verses. It didn’t matter that the crowds of his former fans wanted old Zimmerman back: in 1965, Dylan turned from a folk singer into a rock star.

Further Listens: Highway 61 Revisited, Tombstone Blues

‘Ballad of a Thin Man’

It perhaps seems a little strange that Dylan could ever be associated with the hippie movement. Despite ‘Blowin’ in the Wind,’ he has, indeed, also given birth to some of the harshest and most scornful songs in musical history. The line ‘you just kind of wasted my precious time,’ dedicated to a lover in ‘Don’t Think Twice, It’s All right,’ or songs like ‘Positively 4th Street’ demonstrated it well. However, it seems like Dylan was never as unforgiving as in ‘Ballad of a Thin Man.’ Proof of his profound disdain towards journalists, the song was knowingly written following the musician’s encounter with a journalist from The Times.

Further Listen: Positively 4th Street

‘A Simple Twist of Fate’

Blood on the Tracks is famously a story of pain. Critics unanimously saw the album as Dylan’s confessions on his recent divorce, but the truth is that no one can ever really know. In his autobiographical Chronicles, Dylan casted doubts on this belief: ‘I would even record an entire album based on Chekhov short stories. Critics thought it was autobiographical – that was fine.’ Whether or not Blood on the Tracks was really inspired by Chekhov is a mystery, but the album is a fantastic work regardless. ‘A Simple Twist of Fate’ is perhaps the most poignant of its tracks, seeing Dylan letting go of his love with a merging of nostalgia, regret and resignation.

Further Listens: Tangled Up in Blue, You’re Gonna Make Me Lonesome When You Go

‘Series of Dreams’

‘Series of Dreams’ is another of Dylan’s underappreciated songs that ended up in the Bootleg Series. According to producer Daniel Lavoie, it was originally recorded to be part of Oh Mercy. The song appears as an insight of a man’s dreams, without the tiniest attempt to analyze them. Perhaps this is the reason why it was first cut. Perhaps it was not deep enough to stand next to ‘Political World.’ But even as it is, the song is actually highly enjoyable. The mystery behind the rhythm and words are definitely taking listeners somewhere, and the experience is all the more exhilarating as they don’t know where that somewhere is.

Further Listens: Bob Dylan’s Dream

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