You should know his songs well before he starts singing. With the announcement of his newest album, Rough and Rowdy Ways by Bob Dylan, revisit some of his best songs.
Bob Dylan is releasing his first album of original work in over eight years. To ready yourself before the album drops June 19, here is a list of some of Dylan’s best songs in no hierarchical order.
He Was a Friend of Mine – The Bootleg Series Volumes 1-3 (Rare and Unreleased) 1961-1991
One of Dylan’s earliest recordings, ‘He was a Friend of Mine’ showcased Dylan’s gravitation to covering classic folk songs. Originally recorded in 1939 by John and Alan Lomax from an inmate at the Clemons State Detention Farm, Dylan recorded the song during the sessions for his first album Bob Dylan but left the recording off the final album. Nevertheless, this song is emblematic of a topic that a young Dylan wrote extensively about: friendships with a melancholy edge. “A thousand miles from home / And he never harmed no one / And he was a friend of mine.” Whether it refers to Christ or someone known to that inmate, ‘He Was a Friend of Mine’ is a tried and true ballad.
More like this: ‘Ballad for a Friend’, ‘Bob Dylan’s Dream’, ‘Moonshiner’
A Hard Rain’s A-Gonna Fall – The Freewheelin’ Bob Dylan
What sets this song apart from the rest of The Freewheelin’ Bob Dylan is Dylan’s powerful imagery. With a control of language and symbolism far beyond his years, Dylan channels a modern Arthur Rimbaud, especially the latter’s 100-line poem, ‘The Drunken Boat’. Dylan’s apocalyptic vision in lines like “I saw a black branch with blood that kept dripping” is reminiscient of Rimbaud’s own “I’ve seen fermenting marshes like huge lobster-traps / Where in the rushes rots a whole Leviathan”. ‘The Drunken Boat’, written by the 16-year old French poet, describes a boat lost at sea that eventually sinks. ‘Hard Rain’, written by Dylan on the night of the Cuban Missile Crisis, when the world waited to see whether a Soviet ship would be sunk. Today it’s one of his most recognizable songs, so much so that when Dylan won the Nobel Prize, Patti Smith performed it on his behalf in Sweden.
More like this: ‘Chimes of Freedom’, ‘Lay Down Your Weary Tune’
Don’t Think Twice, It’s All Right – The Freewheelin’ Bob Dylan
It’s one of Dylan’s best love songs and came on so early in his career. ‘Don’t Think Twice, It’s All Right’ was written after his girlfriend and early muse, Suze Rotolo, left to take university classes in Italy. The background comes through the gentle fingerpicking and the lyrics that so accurately sums itself up in the opening lines, “Well it ain’t no use to sit and wonder why, babe / If’n you don’t know by now.” Dylan talked about the song on the liner notes for Freewheelin’: “‘A lot of people make it sort of a love song–slow and easy-going. But it isn’t a love song. It’s a statement that maybe you can say to make yourself feel better. It’s as if you were talking to yourself.”
More like this: ‘Girl from the North Country’, ‘Boots of Spanish Leather’, ‘It Ain’t Me Babe’
When the Ship Comes In – The Times They Are A-Changin’
Joan Baez, a longtime collaborator of Dylan’s and occasional partner, retold the story of ‘When the Ship Comes In’ on the Scorsese-directed documentary No Direction Home. When Dylan went into a hotel that Baez was staying at and asked reception if they had Baez’s room, the hotel said no. When Baez went in and confirmed that the hotel did have a room for Baez, they didn’t acknowledge Dylan, likely for his scruffy demeanor. Dylan wrote ‘When the Ship Comes In’ in a rage that evening, a song that despite lyrics like “The fishes will laugh / As they swim out of the path” hides the reckoning the ship will bring in through Dylan’s vocal delivery. With its Brechtian roots, it’s a powerful song, so powerful that Dylan and Baez both performed it at the March on Washington, before Dr. King delivered ‘I Have a Dream.’
More like this: ‘Masters of War’, ‘Let Me Die in My Footsteps’
The Lonesome Death of Hattie Carroll – The Times They Are A-Changin’
Based off a real incident, ‘The Lonesome Death of Hattie Carroll’ is perhaps Dylan’s greatest protest song. The meter, the structure, the refrain. Dylan exercises his greatest literary gifts to create a chronicle of a racially motivated murder, a song about class and justice. The lines bleed into each other and the long never lets up, a fact that Dylan is acutely aware of, “And you who philosophize disgrace and criticize all fears / Take the rag away from your face / Now ain’t the time for your tears.” When Dylan performed it live on the Steve Allen Show, the audience couldn’t help but cry.
More like this: ‘Who Killed Davey Moore?’, ‘Oxford Town’, ‘Only a Pawn in Their Game’, ‘The Death of Emmett Till’
Seven Curses – The Bootleg Series Volumes 1-3 (Rare and Unreleased) 1961-1991
Although it was left off Times, ‘Seven Curses’ is one of Dylan’s most gut-wrenching ballads of perverted justice, murder, and exploited sex. It packs a punch that levels any hard-hearted listener with Dylan’s strained vocal performance and humble guitar playing.
More like this: ‘Ballad of Hollis Brown’, ‘Percy’s Song’
Mr. Tambourine Man – Bringing It All Back Home
‘Mr. Tambourine Man’ has become anthemic in the popular culture as a drug song. It’s understandable to see the parallels in lyrics that deal with mesmerism, hallucinatory imagery, and those unique run-on sentences. “Yes, to dance beneath the diamond sky with one hand waving free / Silhouetted by the sea, circled by the circus sands / With all memory and fate driven deep beneath the waves / Let me forget about today until tomorrow.” By the end of it, you’ll be calling for Mr. Tambourine Man to play another song.
More like this: ‘Farewell, Angelina’, ‘Changing of the Guard’
Like a Rolling Stone – Highway 61 Revisited
His most famous and acclaimed song, the opening track to his sixth album broke barriers. The barriers of art and commercial music, the folk scene and the mainstream, acceptable song lengths for radio, acoustic and electric. Bruce Springsteen said that the opening snare drum, “kicked open the door to your mind.” It bites and howls, words are stretched to extraordinary lengths, every instrument fights to hold a spot in the harmony of the music. Whole books have been written about the power of this Dylan song, and for good reason too.
More like this: ‘Positively 4th Street’
Ballad of a Thin Man – Highway 61 Revisited
It’s acidic, vicious, unrelenting. ‘Ballad of a Thin Man’ is Dylan at his most violent and angry. Whether it’s the original from Highway 61 Revisited with Dylan slamming the keys on his piano while Al Kooper’s ghost-like organ whistles in the background, or the live version where Dylan would howl the words while the Hawks would play slickly behind him, it’s impeccable. A cat-o’-nine-tails for the journalists who hounded him, Dylan criticizes them for interrogating him for answers they can’t understand, “Because something is happening here / But ya’ don’t know what it is / Do you, Mr. Jones?”
More like this: ‘Can You Please Crawl Out Your Window’, ‘Foot of Pride’
Desolation Row – Highway 61 Revisited
The final track of Highway 61 Revisited, ‘Desolation Row’ is a glimpse at a Dylan born ten years earlier, another one of the Beats that he admired like Ginsberg and Kerouac. An interwoven vignette of literature, the Bible, history, and his own Dylanesque inventions. Dylan told reporters that Desolation Row could be found over the Mexican border, “It’s noted for its Coke factory.”
More like this: ‘Murder Most Foul’
Visions of Johanna – Blonde on Blonde
This is Dylan at his lyrical peak. “Ain’t it just like the night to play tricks when you’re tryin’ to be so quiet?” Originally titled ‘Freeze Out’, ‘Visions of Johanna’ is unrivalled. It’s that Rimbaud-style symbolism with a Nashville edge, Dylan sings of sex and adultery, characters like Louise who holds the handful of rain, the “little boy lost”, the “jelly-faced woman” inhabit some unknown locale. Dylan offers those axioms only he could think of, “Mona Lisa musta had the highway blues / You can tell by the way she smiles”, and purely revolutionary lyrics, “The ghost of electricity howls in the bones of her face.”
More like this: There are none.
One of Us Must Know (Sooner or Later) – Blonde on Blonde
This song embodies Blonde on Blonde as an album. It’s an apology from Dylan to a lover, but as he apologises, he shifts the blame. “I didn’t mean to treat you so bad / You shouldn’t take it so personal.” Dylan pushes agency away from him, he’s become a victim of his own desires, “You just happened to be there, that’s all.” To Dylan, it’s the woman’s actions that determined the end of the relationship. She hid her mouth behind the scarf, she whispered to him asking if he was leavin’ with her or another, she clawed out his eyes when he said he never meant to do any harm. The vitriol is perfect, the drums and organ even more so.
More like this: ‘I Want You’, ‘Most Likely You Go Your Way (And I’ll Go Mine)’, ‘Temporary Like Achilles’
Just Like a Woman – Blonde on Blonde
The women of Blonde on Blonde don’t often share vulnerability alongside Dylan. But here, everyone is vulnerable as Dylan ponders on the impermeability of maturity and the complexity of relationships. It’s one of Dylan’s most refined songs on an album that sounds uniquely raw.
More like this: ‘I’ll Keep It with Mine’
I Shall Be Released – The Bootleg Series Volumes 1-3 (Rare and Unreleased) 1961-1991
The most famous song from Dylan’s Basement Tapes, ‘I Shall Be Released’ has proved an enduring classic in Dylan’s concerts. It’s been covered by Nina Simone, Jerry Garcia Band, Elvis, and dozens more. Performed with The Band in their house Big Pink up in Woodstock, ‘I Shall Be Released’ was the mascot of roots rock and gospel in the late 60s that challenged the psychedelia of The Doors and Jimi Hendrix.
More like this: ‘Goin’ to Acapulco’
I’m Not There – The Basement Tapes Raw: The Bootleg Series, Vol. 11
Another entry in The Basement Tapes sessions, ‘I’m Not There’ showcased Dylan’s ability to make up lyrics on the spot. ‘I’m Not There’ is stream-of-consciousness song about absence that was widely bootlegged for decades before it was released on the Bob Dylan biopic of the same name in 2007.
More like this: ‘Sign on the Cross’, ‘To Fall in Love with You”
All Along the Watchtower – John Wesley Harding
Jimi Hendrix will be forever attributed to the song after his iconic cover on Electric Ladyland. And for good reason; Dylan’s original has nowhere near the flamboyance and extravagance of Hendrix’s version, mainly due to the fact that Dylan didn’t see the song as any outlier above the quality of the album. It’s only because of the Hendrix cover that the song has endured in the mainstream, and perhaps is the reason why it’s become Dylan’s most performed song.
More like this: ‘This Wheel’s on Fire’
I Threw It All Away – Nashville Skyline
Nick Cave was asked once if there was any songs’ he wished he’d written. ‘I Threw It All Away’ was his answer. “There was always something about that song,” Cave said, “that was so simple, and an audacity to this sort of simplicity to that song. But it was so… so powerful at the same time. For me, at least. I was always ragingly envious of that song.” Cave loved the song so much that when he came to new cities, he would go out and buy a new copy of Nashville Skyline. Dylan chose the song for his live debut in years on the first episode of The Johnny Cash Show in 1969.
More like this: ‘Time Passes Slowly’, ‘Alberta #2’
If Not for You – New Morning
There are no great feats of poetry on this song. ‘If Not for You’ is a simple, country love song. “If not for you, my sky would fall / Rain would gather too”. Kicking off New Morning, it sets the tone for a new Bob Dylan, a family man in exile, living in Woodstock. Another version of the song appeared on The Bootleg Series Volumes 1-3 (Rare and Unreleased) 1961-1991 where George Harrison, on guitar, accompanies Dylan.
More like this: ‘Buckets of Rain’, ‘Shooting Star’, ‘Moonlight’
Sign on the Window – New Morning
Whereas on ‘If Not for You’, Dylan sings about love for a woman, ‘Sign on the Window’ is a song about love for family and family life. He’s forsaken a life on the road, a life with many women, for something easier. “Build me a cabin in Utah / Marry me a wife, catch rainbow trout / Have a bunch of kids who call me “Pa” / That must be what it’s all about.”
More like this: ‘Day of the Locusts’, ‘Wedding Song’
Knockin’ on Heaven’s Door – Pat Garrett & Billy the Kid
You’d be hard-pressed to find a more well-known Dylan song. But, just as ‘All Along the Watchtower’ is forever associated with Jimi Hendrix, ‘Knockin’ on Heaven’s Door’ will be remembered in the popular consciousness for the Guns ‘n’ Roses cover. Many wouldn’t know it was a Dylan song, even more wouldn’t know that it was originally written as part of the Sam Peckinpah Western Pat Garrett & Billy the Kid starring James Coburn and Kris Kristofferson.
More like this: ‘Going, Going, Gone’
Tangled Up in Blue – Blood on the Tracks
Blood on the Tracks is possibly the magnum opus of Dylan’s career. Without the thin, wild, mercurial sound of Blonde on Blonde that could prove daunting to casual listeners, Blood on the Tracks is the voice of a mature artist with a firm grasp on what he’s doing. ‘Tangled Up in Blue’ is the most obvious example of this, where Dylan weaves past, present, and future through the first, second, and third person. It’s a Forrest Gump sprint across America, passing through small towns, big cities, and rural countryside. “The only thing I knew how to do / Was to keep on keeping on / Like a bird that flew / Tangled up in blue.”
More like this: ‘Up to Me’, ‘You’re Gonna Make Me Lonesome When You Go’
Idiot Wind – Blood on the Tracks
Perhaps his most aggressive song since ‘Ballad of a Thin Man’, ‘Idiot Wind’ marries that youthful outrage of mid-60s Dylan with the more mature Dylan of Blood on the Tracks. Dylan spits some of his most venomous lines in his oeuvre in this song (“One day you’ll be in the ditch / Flies buzzing around your eyes / Blood on your saddle”) with some of his most honest insights (“I can’t feel you anymore / I can’t even touch the books you read”). His anger burns hard and hot until it’s unsustainable and collapses like a dying star. The vicious songwriter of declarations like ‘Masters of War’ and ‘When the Ship Comes In’ eventually concedes to his own fault and responsibility.
More like this: ‘Pay in Blood’, ‘Honest with Me’, ‘Marchin’ to the City’
Shelter from the Storm – Blood on the Tracks
‘Shelter from the Storm’ transcends into the poetic in ways that very few artists can manage. With Dylan, this effect feels like every other song but especially so with this penultimate piece from Blood on the Tracks. Celebrated writer Stephen King cited this song as one of the best examples of Dylan’s songwriting prowess, “That line ‘ravaged in the corn’ – can you imagine that on a record? It’s just a gorgeous line. And that refrain always struck me as sort of mystic: ‘Come in, she said/ I’ll give you shelter from the storm.’ That incremental repetition – I get goosebumps just thinking about it.”
More like this: ‘You’re a Big Girl Now’, ‘Oh Sister’, ‘When the Deal Goes Down’
Hurricane – Desire
Co-written with playwright Jacques Levy, who also co-wrote the rest of Desire with Dylan, you can hear the impact of theatre in the music. “Pistol shots ring out in a barroom night” reads like a stage direction, right beneath the words ‘Act 1, Scene 1’. ‘Hurricane’ was, and still is, an instantly recognizable Dylan song, perhaps due to the fact there’s been no mainstream cover of the song that appealed to pop sensibilities like Jimi Hendrix, Guns ‘n’ Roses, or Adele. ‘Hurricane’ was Dylan’s first protest song on an album since he shed the Voice of a Generation moniker. The song, based off the true wrongful incarceration of Rubin “Hurricane” Carter, helped free the boxer from prison by bringing awareness to his situation for years.
More like this: ‘George Jackson’
Isis – Desire
It’s a cowboy ballad disguised in mysticism about marital devotion and life on the road. Instrumentally, the album sounds vaguely like world music (reminiscent of Leonard Cohen’s Recent Songs), like Dylan’s been drifting into Spain and Mexico and bringing back the playing styles and instruments of those countries. The version that Dylan performed in Montreal on the Rolling Thunder Revue demonstrates how the song is a perfect representation of mid-70s Dylan.
More like this: ‘Romance in Durango’, ‘Sara’, ‘Mozambique’
One More Cup of Coffee – Desire
Scarlet Rivera’s violin pushes this song into another dimension. Dylan sings about an easily relatable topic, desire for coffee, and elevates it into an outlaw anthem of forbidden love and the danger of staying in one place for too long. Is the Valley Below one more refuge for a renegade at his wits end, or is it somewhere more nefarious?
More like this: ‘Senor’, ‘Where Are You Tonight?’, ‘Billy 4’
Abandoned Love – Side Tracks
The song that inspired Dylan to make Desire, this outtake was debuted live at the Bitter End, a New York club, in the mid-70s. Dylan, after making a surprise appearance backing up Ramblin’ Jack Elliot, borrowed Elliot’s guitar and performed the song to a stunned crowd. The song was left off the album unfortunately, but both Dylan’s live performance and its studio recording are much beloved outtakes.
More like this: ‘Make You Feel My Love’, ‘Where Teardrops Fall’
Slow Train – Slow Train Coming
This rocker off Dylan’s first Gospel album from his born-again phase is less of evangelical then ‘Gotta Serve Somebody’ and ‘Precious Angel’, instead focusing on the sins of global economics and politics. He warns of the slow train coming as an undeniable threat, looming on the horizon and nearly forgotten under the hedonistic self-involvement of capitalism.
More like this: ‘The Groom’s Still Waiting at the Altar’, ‘Solid Rock’, ‘Gotta Serve Somebody’
In the Garden – Saved
Dylan’s most evangelical work, Saved is filled with preaching and prayer. It’s an underrated album, more spiritually concise than its predecessor’s rock roots and better written and produced than most of the songs on Shot of Love (looking at you ‘Lenny Bruce’). Songs like ‘Pressing On’, ‘Solid Rock’, and ‘What Can I Do for You?’ stand out as highlights, alongside this often-overlooked number. Its lyrics are strong, the piano, organ, and back-up vocals even stronger. It’s emotionally charged and evokes the Gospel to a powerful degree. Dylan named it as one of the two songs of his that he felt was underappreciated.
More like this: ‘I Believe in You’, ‘Dear Landlord’
Every Grain of Sand – Shot of Love
When Shot of Love was released in 1981, one critic derided the album for only having one masterpiece. Dylan’s peer Leonard Cohen defended the album, saying “My God! Only one masterpiece! Does this guy have any idea what it takes to produce a single masterpiece?” That masterpiece, ‘Every Grain of Sand’, is undoubtedly one of Dylan’s most harrowing and moving songs. It moves away from the physical strata into the metaphysical and transcendent. “I am hanging in the balance of the reality of man / Like every sparrow fallen / Like every grain of sand.”
More like this: ‘Angelina’
Caribbean Wind – Side Tracks
Excluded from Shot of Love, this love song is full of energy and force. The enthusiastic deep breathes of the back-up singers, the lyrics that exude a tropical heat, empowered vocals by Dylan, another force-of-nature lover. This charismatic spiritual transcends the need to evoke the name of G-d, its religiosity bound to the fabric of music.
More like this: ‘Heart of Mine’, ‘Tell Me’, ‘Ye Shall Be Changed’
Jokerman – Infidels
Dylan returned to the secular – well the semi-secular anyway – with Infidels. ‘Jokerman’, the album’s opening track, carries the relaxed atmosphere of ‘Caribbean Wind’ into a Jesus allegory (maybe). With Dire Strait’s member Mark Knopfler producing the album, ‘Jokerman’ is a pleasant exit from the divisive Gospel albums of those recent years and a compelling introduction to an enjoyable album.
More like this: ‘Don’t Fall Apart on Me Tonight’, ‘Silvio’, ‘Under Your Spell’
I and I – Infidels
In a conversation between Bob Dylan and Leonard Cohen, Dylan asked Cohen how long ‘Hallelujah’ took to write. “Two years,” lied Cohen (in reality, Cohen wrote the song over a five-year period). Cohen asked Dylan how long ‘I and I’ took. “Fifteen minutes,” replied Dylan. Listening to ‘I and I’, you can hear similarities in the lyrics to ‘Hallelujah’. Cohen’s King David who plays the secret chord is like Dylan’s righteous king writing psalms, her bathing in the moonlight and him beside moonlit streams, the woman who draws out a Hallelujah from Cohen and the stranger speaking with Dylan’s mouth.
More like this: ‘Death is Not the End’, ‘Rank Strangers to Me’, ‘Dark Eyes’
Blind Willie McTell – The Bootleg Series Volumes 1-3 (Rare and Unreleased) 1961-1991
Considered one of Dylan’s best outtakes, ‘Blind Willie McTell’ was meant to be included on his 1983 release Infidels but was left out. The piano and Dylan’s vocals work together to create a haunting journey to the 1930s, a temporal and spatial shift comparable to any good Neil Young song. “Them charcoal gypsy maidens / Can strut their feathers well / But nobody can sing the blues / Like Blind Willie McTell.”
More like this: ‘Tin Angel’, ‘Scarlet Town’, ‘Spirit on the Water’, ‘Cold Irons Bound’
Brownsville Girl – Knocked Out Loaded
One of Dylan’s best songs of the 1980s, ‘Brownsville Girl’ (co-written with playwright legend Sam Shepard) is the highlight of what is arguably Dylan’s weakest album Knocked Out Loaded. Dylan sings with a casual rhythm that is immediately engrossing, inviting us across the Texan landscape, through places like the Alamo, San Antonio, and Corpus Christi. With levels of time and space stacking up on identity after identity, you’ll get lost alongside Dylan in this road-trip of a song.
More like this: ‘Lily, Rosemary and the Jack of Hearts’, ‘Black Diamond Bay’, ‘Highlands’
Dirty World – The Traveling Wilburys Vol. 1
While not strictly a Bob Dylan album, ‘Dirty World’ is a refreshing taste of Dylan working alongside his contemporaries in a way never really seen before (unless you count Dylan’s contribution to ‘We Are the World’). As a member of the folksy supergroup The Traveling Wilburys alongside George Harrison, Tom Petty, Roy Orbison, and Jeff Lynne, Dylan kinda joined by accident. When Harrison needed to record a B-side single on short notice, he called Dylan and asked to use his garage studio along with the other three future Wilburys. While the four recorded the single, Dylan kept his guests provided for by barbequing chicken. Harrison invited Dylan to do some writing with them for what would become the hit ‘Handle with Care.’ Deciding to use the song for something else, the group decided to form the Traveling Wilburys where Dylan wrote a number of songs, including the raucously funny ‘Dirty World’.
More like this: Just listen to the two albums the Wilburys released, they’re gold.
Most of the Time – Oh Mercy
Before Time Out of Mind, critics and followers rejoiced at Oh Mercy as Dylan’s comeback album. And they were correct, because Oh Mercy lead the way for Dylan of the new millennium. Dylan’s best album since Infidels hit the heights of Desire and John Wesley Harding. Spirituals like ‘Ring Them Bells’, jaunty rockers like ‘Everything is Broken’, and ambient apocalypses like ‘Man in the Long Black Coat’. But arguably the album’s highlight comes in ‘Most of the Time’, a façade against the depression of solitude. Reminiscent of Johnny Cash’s ‘Guess Things Happen that Way”, Daniel Lanois’ atmospheric production style nails the style that Dylan should’ve strived for during the eighties.
More like this: ‘What Was It You Wanted’, ‘What Good Am I?’, ‘Standing in the Doorway’
Series of Dreams – The Bootleg Series Volumes 1-3 (Rare and Unreleased) 1961-1991
With some of Dylan’s most surrealistic imagery, ‘Series of Dreams’ was originally meant for Oh Mercy and was a favourite of producer Daniel Lanois. But Dylan never felt entirely comfortable with the recordings and scrapped it from the record. But amidst a treasure trove of outtakes and unreleased songs, ‘Series of Dreams’ is special.
More like this: ‘Dignity’
Born in Time – Tell Tale Signs: The Bootleg Series, Vol. 8
Although Dylan released it on his panned 1990 album Under the Red Sky, the beauty of ‘Born in Time’ shines through on the outtake featured in the eighth entry into The Bootleg Series. Eric Clapton covered it to popular acclaim, but this original version recorded for Oh Mercy hits new heights for the song.
More like this: ‘Dreamin’ of You’
Delia – World Gone Wrong
Of the two traditional folk albums that Dylan released in the early 1990s, this song from World Gone Wrong is gut-wrenching. Dylan’s cover of ‘Delia’ brings an ennui and melancholy to the song that focuses not on the violence of the murder, but on the effects of loss. “All the friends I ever had are gone,” Dylan sings in the refrain. This song is the perfect representation of Dylan’s overlooked cover albums from the 90s.
More like this: ‘Blackjack Davey’, ‘Love Henry’, ‘Tomorrow Night’, ‘Lone Pilgrim’, ‘Blood in My Eyes’
Trying to Get to Heaven – Time Out of Mind
“The air is getting hotter” Dylan sings, “There’s a rumbling in the sky.” Heat and storms are a constant in Dylan songs, often to address death and mortality. In ‘Trying to Get to Heaven’, heat, storms, and death are part of the land. The allusions within the song are numerous and keeps Dylan company as he laments his sorrows and memories but can’t help but push forward.
More like this: ‘Man in the Long Black Coat’
Not Dark Yet – Time Out of Mind
It’s Dylan’s most depressing song, without a doubt. “I was born here and I’ll die here against my will”, “Feel like my soul has turned into steel”, “Well, my sense of humanity has gone down the drain / Behind every beautiful thing, there’s been some kind of pain.” It’s an unrelenting melancholy and one of Dylan’s most atmospheric compositions.
More like this: ‘If You See Her, Say Hello’, ‘One Too Many Mornings’, ‘Tomorrow is a Long Time’, ‘Dirge’
Mississippi – Tell Tale Signs: The Bootleg Series, Vol. 8
Originally meant for Time Out of Mind, Dylan left this song in his vault until 2001’s “Love and Theft”. The album’s release on 9/11 made this album all the more poignant, especially the line “Sky’s full of fire, pain is pouring down” from this song. And although the 2001 version is enjoyable, it pales in comparison to the first outtake meant for Time Out of Mind and then released in 2008’s Tell Tale Signs: The Bootleg Series, Vol. 8. It’s a gut-wrenching song about the clarity that comes with mistakes and the etherealness of love.
More like this: ‘Red River Shore’, ‘Roll on John’
High Water (For Charley Patton) – “Love and Theft”
Another entry into Dylan’s apocalyptic visions of the future, ‘High Water (For Charley Patton)’ refers to both a song by the same name as pioneering blues musician Charley Patton and the Great Mississippi Flood of 1927 that Patton sung about. The flood, which decimated the African American community, was the most destructive flood in U.S. history and led to the country creating its iconic floodways and levees. Dylan’s song channels this destructive power and resulting reformation of infrastructure, as well as the racial component of the disaster, to engage with American history’s necessity to destroy in order to progress, i.e. the Civil War into the Reconstruction era.
More like this: ‘Lonesome Day Blues’, ‘The Wicked Messenger’, ‘Narrow Way’
Workingman’s Blues #2 – Modern Times
It’s late-day Dylan at his peak. This phenomenal song from the bluesy Modern Times is an Ovidian discourse on economic and political perils. Dylan sings the experiences of the small-town inhabitants in a way that rivals Bruce Springsteen for the title of the workingman’s hero.
More like this: ‘Early Roman Kings’, ‘Beyond the Horizon’, ‘North Country Blues’
Ain’t Talkin’ – Tell Tale Signs: The Bootleg Series, Vol. 8
Dylan opens this song with one of his most apocalyptic couplets, “As I walked out tonight in the mystic garden / The wounded flowers were dangling from the vine.” In ‘Ain’t Talkin’’, Dylan brings in every garden from the Bible’s Eden to Ezra Pound’s depiction of Kensington Gardens in this sauntering threat. The original final track from Modern Times is more mystically atmospheric, but the outtake on Tell Tale Signs is slightly superior with its musicians playing like they’re banging on the drums of war.
More like this: ‘Beyond Here Lies Nothin’’, ‘False Prophet’
Must Be Santa – Christmas in the Heart
To represent Dylan’s fun side, an aspect of him that this list has overlooked, his Christmas hit ‘Must Be Santa’ is the perfect ambassador. A joyful slurring of instruments and vocals, it flows with the energy of a party still going strong at two in the morning.
More like this: ‘Wiggle Wiggle’, ‘All I Really Want to Do’, ‘Country Pie’, ‘Wigwam’
Duquesne Whistle – Tempest
Written with the Grateful Dead’s Robert Hunter (who previously collaborated with Dylan on Together Through Life), ‘Duquesne Whistle’ is infectiously Mid-Western, like Dylan’s wandering through his hometown, seeing the old railroads and the trees with the faded love-hearts carved in. The music video is an equal delight, directed by Australian filmmaker Nash Edgerton and featuring his brother, actor Joel Edgerton.
More like this: ‘Life is Hard’, ‘Forgetful Heart’, ‘This Dream of You’
Soon After Midnight – Tempest
‘Soon After Midnight’ is Dylan with a delicacy and sensitivity that contrasts the rough-and-tumble of his voice and songs like ‘Pay in Blood’ or ‘Tin Angel’, both from Tempest. The gentle melody has proven itself to be one of Dylan’s favourites in performance.
More like this: ‘I Contain Multitudes’, ‘Simple Twist of Fate’, ‘Huck’s Tune’
That Lucky Old Sun – Shadows in the Night
Well, this list is pretty long and not even every album has been represented (only 24 of Dylan’s 38 studio albums have had a least one song discussed). And, to surmise an entire period of Dylan, his cover of ‘That Lucky Old Sun’ is one of the highlights of his three Great American Songbook albums. His vocal performance is astounding and the production of these albums are perfection.
More like this: ‘Stardust’, ‘Why Try to Change Me Now?’, ‘Some Enchanted Evening’, ‘Melancholy Mood’, ‘I Could Have Told You’
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