As we mark the anniversary of the release of Bob Dylan’s sophomore album, the iconic The Freewheelin’ Bob Dylan, we thought what better way to celebrate than by ranking all the songs on the album from worst to best. Mainly, it has to be said, because we like a challenge and labelling one song from this record as ‘the worst’ is about as challenging as it gets.
The second album from Bob Dylan saw the young folk singer assert himself not only as a writer and singer but as a growing figurehead of the New York scene, later being referred to as the “Spokesman of a Generation” — a title he repudiated.
With Freewheelin’ Dylan created one of the most iconic records of the 1960s and its presence can still be felt to this day. The album is full of classic Dylan moments and through his clever lyricism, it firmly shone a light on the singer’s growing songwriting ability. Dylan’s self-titled debut had only included two original songs, eleven of the thirteen tracks on Freewheelin’ are Dylan’s own.
Opening with ‘Blowin’ in the Wind’ the album doesn’t slow up and sees Dylan lay down a selection of his songs that are often regarded as the best of his six-decade-long career. Recorded in 1962 at Columbia’s studios in New York, Dylan channelled the unrest of the new generation and littered his musical commentary with topical and political lines.
Much of this new intrigue has been attributed to Suze Rotolo, the daughter of two active members of the American Communist Party, whom the love songs in the album can be attributed to too. Rotolo is also the woman who joins Dylan on the iconic cover art of the album, about which Rotolo said: “It is one of those cultural markers that influenced the look of album covers precisely because of its casual down-home spontaneity and sensibility.”
Rotolo added: “Most album covers were carefully staged and controlled, to terrific effect on the Blue Note jazz album covers … and to not-so great-effect on the perfectly posed and clean-cut pop and folk albums. Whoever was responsible for choosing that particular photograph for The Freewheelin’ Bob Dylan really had an eye for a new look.”
When you put all these elements together, it makes for an album that is charged with personality, politics and wisdom beyond Dylan’s young age. Below we rank the songs on Bob Dylan’s iconic album The Freewheelin’ Bob Dylan.
Ranking Bob Dylan’s The Freewheelin’ Bob Dylan from worst to best:
‘Honey, Just Allow Me One More Chance’
Based on a song dating back to the 1890s, originally titled ‘Honey, Won’t You Allow Me One More Chance?’, Dylan brings the song into the new century with a folk-spun harmonica and a jumping guitar rhythm.
It’s often noted as one of the aforementioned moments of longing. With love interest Suze Rotolo in Italy studying Art, Dylan was left penning letters to his lost-love. This adaptation of a classic is another example of his ear for a tune.
‘Bob Dylan’s Dream’
Based on the melody of the traditional song ‘Lady Franklin’s Lament’, a song that sees the titular character dream of finding her long-lost Arctic exploring husband, Sir John Franklin.
Dylan may well maintain the melody of the lamenting track but he turns the track into a more personal journey despite continuing the theme of longing from the original ballad.
Originally recorded by the Mississippi Sheiks and later by their band leader Bo Carter back in 1928, Dylan puts his new-age spin and turns the song into a longing city billy gem. The song has been widely covered by artists just as Bob Wills, Big Joe Turner and more.
It speaks to Dylan’s sensibilities, namely looking to the purity of the past to help navigate his new sound through the growing dangers of the new decade.
‘Talkin’ World War III Blues’
Woody Guthrie, an undoubted key influence in the early moments of Bob Dylan’s career, created his spontaneous songwriting style under the moniker of “talkin’ blues.” It was something Dylan paid homage to in 1960 during a rare Minneapolis recording back in 1960, covering Gutherie’s ‘Talking Columbia’ and ‘Talking Merchant Marine’.
Dylan would pay the ultimate compliment though on his second album when he spontaneously composed ‘Talkin’ World War III Blues’, recording five take sof the track and selecting the fith for the album.
‘Down the Highway’
Dylan shook out his folk roots and returned instead to the south and found himself some 12-bar blues. In the sleeve notes of Freewheelin’, Dylan explained to Nat Hentoff: “What made the real blues singers so great is that they were able to state all the problems they had; but at the same time, they were standing outside of them and could look at them. And in that way, they had them beat.”
But once again the missing figure of Suze Rotolo can be felt in this track with the lyric: “My baby took my heart from me/ She packed it all up in a suitcase/ Lord, she took it away to Italy, Italy.”
‘Bob Dylan’s Blues’
Another blues number sees Dylan introduce the song with some smirking spoken word as he sarcastically says: “Most of the songs that are written uptown in Tin Pan Alley, that’s where most of the folk songs come from nowadays,” later saying “this was written down in the United States.”
What follows is a somewhat absurd set of lyrics that sees Dylan trawl through the tropes of Americana and lay them down backed by his now growing harmonica work. In the sleeve notes, Dylan says it was “a really off-the-cuff-song. I start with an idea and then I feel what follows. Best way I can describe this one is that it’s sort of like walking by a side street. You gaze in and walk on.”
‘I Shall Be Free’
The song is a re-write of Lead Belly’s ‘We Shall Be Free’ and has been performed by notable folkies throughout the years with Woody Guthrie’s version providing a more stable foundation from which Dylan builds his own take.
A seemingly lightweight track placed at the end of an album highlighted that Dylan was either still very green around the gills and didn’t read the lay of his previous songs or that he possessed a heavy dose of musicianship, knowing the moment of reprieve would be welcomed after such a heavy album. Either way, it’s a joy to listen to.
A snark and sardonic account of the events which took place at the University of Mississippi in September 1962 when U.S. Air Force veteran James Veteran was the first black student to enrol at the school, situated just a mile or so outside the city of Oxford Mississippi.
Dylan detailed the struggles Meredith faced in just trying to better his education. As he began to attend classes he was met with protests and Mississippians demanding the school be kept segregated, even including Governor Ross Barnett. Dylan was bravely stepping into the civil rights conversation and soon became another trusted ally in the demands.
“Couldn’t get in, all because of the colour of his skin, what do you think of that, my friend?” sings Dylan, appealing to the logical swathes of a new generation, it was a moment of protestation that would add to Dylan’s growing iconography.
‘Masters of War’
The third song of the album, ‘Masters of War’ is perhaps the most arresting a simple and plain protest song. That’s not to say that Dylan’s imagery and poetry aren’t as vivid as ever, more that they are so intently barbed that it is difficult to see anything else.
Aimed directly at the industry of war, the song is based on the arrangement of Jean Ritchie’s ‘Nottamun Town’, and Old English riddle song. The track was composed in late 1962 as Dylan visited London and was even performed around the growing scene during his stay.
It’s about as deliberately scathing as you’re likely to hear. We can’t imagine anyone being so pointed at the establishment these days.
‘Girl From The North Country’
The track has long been heralded as one of Bob Dylan’s finest. Shared and covered by some of the greats, including some special moments via Dylan’s friend, Johnny Cash, the track remains a touching moment on an otherwise intense record. Though he returned to the track in 1969 on Nashville Skyline the first version of the song is charged with antiquity.
Though the titular girl from the song has been cited as Rotolo as well as his hometown girlfriend, Clinton Heylin suggests that song was actually for Bonnie Beecher, a girlfriend of Dylan’s during his time at the University of Minnesota.
Based on the tune from ‘Scarborough Fair’, which itself was based on ‘The Elfin Knight’, Dylan’s lyrics see a mythical creature pose an innocent girl a series of questions. Many have suggested that this peak Bob Dylan, placing his audience in the cold north while waxing lyrically about the troubles and trifles of the world.
‘A Hard Rain’s A-Gonna Fall’
Arguably one of Bob Dylan’s most beloved songs of all time, the singer was only 21-years-old when he wrote the number. Debuted in the smoky Gaslight Cafe in New York, Village performer Peter Blankfield, who was there, recalled: “He put out these pieces of loose-leaf paper ripped out of a spiral notebook. And he starts singing [‘Hard Rain’] … He finished singing it, and no one could say anything. The length of it, the episodic sense of it. Every line kept building and bursting”
The track is deeply poetic and entirely captivating. Reading through like a prophetic novel, Dylan’s imagery is perhaps never more vivid than here. In fact, they were so vivid that the track was often misaligned to the Nuclear Disarmament effort, suggesting the ‘hard rain’ in question was atomic.
“No, it’s not atomic rain, it’s just a hard rain. It isn’t the fallout rain,” reflected Dylan with Studs Terkel at the time. “I mean some sort of end that’s just gotta happen… In the last verse, when I say, ‘the pellets of poison are flooding the waters’, that means all the lies that people get told on their radios and in their newspapers.”
The song represents not only the beginning of a songwriting revolution but the first moments of Bob Dylan’s dominance.
‘Don’t Think Twice, It’s All Right’
Another adapted melody, this time from Paul Clayton’s song ‘Who’s Gonna Buy You Ribbons (When I’m Gone)’, doesn’t mean that Dylan doesn’t contribute his entire heart to this number. A small, somewhat irreverent track in comparison to some of the grandiose themes of the previous 11 songs, but somehow this track feels one of the purest.
Despite Dylan saying, “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,” it’s hard to ignore the overtones of Rotolo’s residence in Perugia, Italy. Still, the duplicity of its meaning again highlights Dylan’s growing poetic technique.
As close to a pop song as Dylan ever really gets, ‘Don’t Think Twice It’s All Right’ still manages to intently and acutely describe the undulating emotions of longing and lost love. It’s a masterstroke of composition and nous.
‘Blowin’ in the Wind’
Quite possibly the greatest album opener of all time, ‘Blowin’ in the Wind’ should take the title as the most beloved folk song ever. Dylan’s track has since become a bastion of free-spirit, open-mindedness and the notion that, for a small piece of acceptance, humanity may be at peace.
Dylan had somewhat adapted the old spiritual song ‘No More Auction Block’ a song sung by former slaves who fled Canada as Britain abolished slavery in 1833. It’s something Dylan acknowledged in 1978, “‘Blowin’ in the Wind’ has always been a spiritual. I took it off a song called ‘No More Auction Block’—that’s a spiritual and ‘Blowin’ in the Wind’ follows the same feeling.”
Though Dylan wouldn’t make the song world-famous, that would be left to Peter, Paul and Mary’s cover of the track—but it did mark a change in Dylan’s songwriting. It moved him from a deeply personal writer to him taking the podium for an increasingly disillusioned generation.
It remains an iconic moment in music history and has become a ubiquitous soundtrack to the futility of fighting against freedom. It cemented Bob Dylan as the poster boy of civil liberties and made him a cherished cultural figurehead forevermore.