Best Bob Dylan Songs of the 1960’s

Bob Dylan Songs

Photo: By Jean-Luc (originally posted to Flickr as Bob Dylan) [CC BY-SA 2.0 (], via Wikimedia Commons

On the cold streets of Minneapolis, Minnesota, in the late 1950’s, a band by the name of Elston Gunn would feature a young University of Minnesota student that would go on to become one of the greatest legends in popular music history. Dropping out of college and moving to New York City in 1960, Bob Dylan began his career performing in the local coffeehouses of Greenwich Village. It was in the dimly lit coffeehouses where Bob Dylan paid tribute to his hero Woody Guthrie and honed his craft. In 1962, Bob Dylan was signed to Columbia Records and released his first album appropriately titled Bob Dylan. However, it was the release of his second album, The Freewheelin’ Bob Dylan that set the stage for Bob Dylan’s emergence as one of the world’s most treasured artists.

The nineteen sixties have been regarded as the most turbulent decade in the history of the United States. What began with the assassination of President Kennedy in 1963, ended with the Woodstock festival in 1969 during the so called Summer of Love. In between, the Vietnam War raged onward continuing into the 1970s. The civil rights movement and assignation of Martin Luther King Jr divided a nation amongst racial tensions that still resonate in the present day. The invasion of British rock bands led by the Beatles and Rolling Stones, along with the sounds of Motown, looked to distract the public from the pain and bitterness of war, racism, and politics. However, for those who could not be silent, they found a voice in the works of Bob Dylan.

For the early part of the decade, Bob Dylan wrote songs that dealt with the sentiments of the anti-war protester, lingering civil rights issues, and the mistrust of government. As Bob Dylan became the voice of a generation, his lyrics came under intense analyzation by fan and foe. “A Hard Rain’s A-Gonna Fall,” was one example of a Bob Dylan lyric becoming generally misinterpreted. In the song, Bob Dylan wrote, “The pellets of poison are flooding the waters.” Most people assumed the lyrics were in response to the concern of nuclear fallout in the wake of the Cold War and Cuban Missile Crisis. However, Bob Dylan later explained that the Hard Rain lyrics were not about nuclear rain, but rather defined the rain of lies presented to the public through newspapers, television, and radio.[1]

For Bob Dylan, the frustration began to rise over the intense analyzation, and at times misinterpretation of many of his lyrics. In 1965, Bob Dylan set out to escape the troubadour protester label, and caused greater furor with his electric set at Newport, Rhode Island. However, soon after the Newport concert in the same year of 1965, Bob Dylan released what may have been his finest work in the album Highway 61 Revisted. The album would soon be followed by another work of art entitled Blonde on Blonde. In 1966, Bob Dylan was involved in a motorcycle accident that sent him into seclusion for over a year. Bob Dylan returned in 1968 with the John Wesley Harding album and then closed out the decade with a country-themed album entitled Nashville Skyline.

As we begin our Bob Dylan project here at it was easily apparent there was no possible way to create a top 10 Bob Dylan songs list that spanned Dylan’s entire career. As much as we enjoy creating those lists for various artists, there are some artists that we have stayed away from based on the depth of their catalogs. Nonetheless, this website was created to serve as a historical site with hopes of introducing essential material to a young audience not familiar with the legends of rock and roll.

While at the same time we mean to entertain and create conversation among our older readers, our long term goal is to serve the youth community as a friendly based site that will inspire our audiences to listen to some of the greatest moments in classic rock history. So in order to present some of Dylan’s finest moments, the project will be broken up into decades. I have asked Brett Stewart to revisit the Bob Dylan 1960’s period. Brett Stewart is a journalist out of Chicago with a wealth of experience in rock and roll journalism. But beyond Brett Stewart’s journalistic experiences, also lay the prose of a poet.  Brett was a perfect choice to pen these works. We hope you enjoy these articles.

Brian Kachejian

Editor and Chief

Best Bob Dylan Songs: 1960’s

By Brett David Stewart

One of the most difficult tasks a musical critic can ever be tasked with is arranging the music of Bob Dylan’s catalog in any form of definitive list. America’s finest troubadour is an enigmatic one; his music means something different and new to everyone who has or will stumble across its great expanses. The foundation for that legendary catalog is the array of lyrical and instrumental creations the poet released in the 1960s. Thus, let’s explore ten of those songs in descending over.

# 10 – ‘Queen Jane Approximately’ – ‘Highway 61 Revisited’ – 1965

Bob Dylan’s catalog in the 60s is often centralized around the landmark 1965 endeavor, ‘Highway 61 Revisited.’ While its iconic opening track, ‘Like A Rolling Stone,’ is deserving of its place in rock history, the opening track of the opposite side of the record is equally memorable. ‘Queen Jane Approximately’ is often the forgotten gem of ‘Highway 61 Revisited.’

Lyrically, ‘Queen Jane’ explores some of the most compelling lyrical content of the entire album. “Won’t you come see me, Queen Jane?” feels like a spiritual brother to the former side’s “How does it feel?” Dylan’s youthful, even accusatory tone on these songs is unlike anything else in his whole catalog. Plus, that screeching harmonica solo before the final verses of the song? Timeless.

# 9 – ‘I’ll Keep It With Mine’ – Recorded in 1966 / Released On ‘Biograph’ 1985

‘I’ll Keep It With Mine’ is one of those special tunes that Bob Dylan wrote but never found a good place for on one of his albums. Instead, it’s become a staple of bootleg releases and other artists’ catalogs. (Judy Collins and Nico enjoyed significant success with it.) The track is one of Dylan’s most well-written ballads.

The piano instrumentation is impeccable, Dylan’s signature croon is in fine form, and the cascading organs floating in the backdrop are a sonic treat. The track was eventually released on ‘Biograph’ in 1985. It’s also been released several times in Dylan’s official ‘Bootleg Series.’ Last year, the 18 disc set of ‘The Cutting Edge’ gave insight into the song’s creation, too, with nearly a full CD’s worth of instrumental takes of the track. (None of which sound like the finalized renditions with vocals, by the way.) It’s a gem of Dylan’s 60s escapades.

 # 8 – ‘Mr. Tambourine Man’ – ‘Bringing It All Back Home’ – 1965

Like with ‘I’ll Keep It With Mine,’ last year’s ‘The Cutting Edge’ release provided insight into the pivotal ‘Mr. Tambourine Man.’ Dylan played the track with full bands, on the piano, and in different keys on acoustic guitar. Ultimately, the studio cut in 1965 was accented with Dylan’s guitar and simple, soft electric guitar musings. The track is, quite simply, the pinnacle of Bob Dylan’s poetic lyricism. It was also a repurposing of his talent, choosing abstract poetic lyricism over ‘voice of a generation’ political rhetoric.

“Yet 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.”

# 7 – ‘Sad-Eyed Lady of the Lowlands’ – ‘Blonde on Blonde’ – 1966

The abstract lyrical explorations of ‘Mr. Tambourine Man’ eventually lead to Dylan’s self-described “best song he ever wrote” – ‘Sad-Eyed Lady of the Lowlands.’ The track, which defied common practice for its time by occupying the entire fourth side of the album, is one of Dylan’s most extravagant jaunts through wordsmithing. The track proved you could put out an eleven minute song that remains consistently interesting. More so, it proved that doing so wouldn’t derail the consumability of the album.

‘Sad-Eyed Lady of the Lowlands’ is chock-full of veiled references to Dylan’s then-wife, Sara, even poking at her previous husband, the photographer Hans Lownds. Later, on 1976’s ‘Desire,’ Dylan openly admitted this on the track entitled ‘Sara,’ a love ballad to his marriage shortly before its inevitable demise. Is ‘Sad Eyed Lady of the Lowlands’ the ultimate expression of love, frustration, or jealousy? That’s for you to decide. It’s a track that’s kept Dylanologists busy for decades.

 # 6 – ‘The Times They Are A-Changin’ – ‘The Times They Are A-Changin’ – 1963

Right out of the gate with this entry, an honorable mention must go to ‘Blowin’ In The Wind.’ It’s a superb civil rights ballad that remains one of Dylan’s most sung songs. That said, ‘The Times They Are A-Changin’ dwarfs it in several ways. The song’s straightforward, yet poetic nature is a direct slap in the face to those standing in opposition of social justice and impending change. It remains relevant to every single civil movement, and always will. When Dylan performed the song for President Obama in 2010, it was as poignant as it was in 1963, concreting its importance as a rally-cry for freedom and vital change.

“If your time to you is worth saving, then you better start swimmin’ or you’ll sink like a stone.”

(Below is the original track and the White House performance mentioned above. It’s perhaps the most dramatic dichotomy between old and young Bob Dylan performing the same song with equal meaning – it’s a very powerful performance.)

 # 5 – ‘It’s Alright, Ma (I’m Only Bleeding)’ – ‘Bringing It All Back Home’ – 1965

Will this song have critics and fans scratching their heads for another fifty-plus years? Probably. Is that’s why it’s one of Dylan’s best efforts? Most definitely. This seven minute epic includes some of the folk hero’s most profound lyrical insights. Even instrumentally, its sparse but stark delivery is unlike anything else ever recorded. Dylan’s societal analysis is on target, taking shots across the bow at consumerism, religion, and the president with one of the most quotable lines in his entire catalog.

“Even the President of the United States sometimes must have to stand naked.”

# 4 – ‘My Back Pages’ – ‘Another Side of Bob Dylan’ – 1964

‘Another Side of Bob Dylan’ is an historically important album. Recorded in one evening in just several takes, the album was an indication of two things: Dylan’s creative spark was igniting even brighter than ever before, and because of this, this would likely be the last time Bob Dylan would serenade fans by himself with a guitar. (In this decade, at least. Yes, Dylan returned to the style frequently in later decades.)

‘My Back Pages’ is one of the most powerful songs on the record. “I was so much older then; I’m younger than that now,” he wails over a very simplistic acoustic guitar. It’s an existential crisis of sorts, as if the song is Bob Dylan struggling to analyse his own musical and personal identity. Given Dylan’s penchant for dramatic and abrupt shifts in style, one can imagine that identity is never quite done forming.

 # 3 – ‘Like A Rolling Stone ‘ – ‘Highway 61 Revisited’ – 1965

Yes, here it is, the track from Dylan’s 60s catalog that’s most instantly recognizable. ‘Like A Rolling Stone’ is the rock and roll track. ‘Bringing it Back Home,’ released earlier in the year, toyed with the idea of combining Dylan’s signature poetry with rock and roll. This opening track of the subsequent album, though, is the most intense manifestation of that idea.

The spider-web effect of inspiration that ‘Like A Rolling Stone’ created across the world is entirely incalculable. Fortunately, we can always leave it to Bruce Springsteen to attempt to calculate it:

“… on came that snare shot that sounded like somebody had kicked open the door to your mind… The way that Elvis freed your body, Dylan freed your mind.”

The turning point of music in the 1960s was when John Lennon wanted to be like Bob Dylan and Bob Dylan wanted to be like John Lennon. ‘Like A Rolling Stone’ was Dylan’s first attempt to do that, opening himself up the intense world of rock and roll.

# 2 – ‘Don’t Think Twice, It’s All Right’ – ‘Freewheelin’ – 1962

‘Don’t Think Twice, It’s All Right’ is a peaceful, but frustrated goodbye to Suze Rotolo, the girlfriend walking with Dylan through Greenwich Village on the cover of ‘Freewheelin.’ When she decided to stay in Italy for longer than the several months she had planned to,

it created a harsh rift in her relationship with a young, somewhat brash Bob Dylan.

‘Don’t Think Twice’ has one of the most stunning melodies in Dylan’s repetoire, which is why it’s a track that’s been performed 936 times by the man since its last rendition in 2015. It’s the perfect goodbye and the perfect end to a relationship. Its reality acknowledges the pain of the loss, but also moves on toward a brighter future. Even though Dylan attempts to be apathetic to the situation, the song is anything but. It emotionally waves farewell to a lost relationship.

“I once loved a woman, a child I’m told. I gave her my heart, but she wanted my soul.”

# 1 – ‘Visions of Johanna’ – ‘Blonde on Blonde’ – 1966

‘Visions of Johanna’ is yet another one of those songs that Bob Dylan experimented with heavily, as evident in the last several ‘Bootleg Series’ releases. The final version, however, the one on ‘Blonde on Blonde,’ is one of his most definitive masterpieces. Some interpreters claim the song is about Joan Baez. Others claim it hints at early fragments in his relationship with Sara. Its green pastures of depth are seemingly endless, thus inciting equally endless interpretations.

The track is remarkably cinematic, yet simultaneously subtle. As Dylan ventures through parking lots, trains, museums, and dimly lit rooms, he makes decisively vague, yet intensely poetic observations of his characters. It also offers quite an expanse of emotion across ‘Blonde on Blonde.’ It’s prefaced by the raucous that is ‘Rainy Day Woman #12 & 35’ and ultimately followed by songs like ‘I Want You’ and ‘Just Like A Woman.’ In it’s own way, however, it stands taller and more peculiarly than those other ‘Blonde on Blonde’ tracks. It’s a masterpiece in itself, a diamond amidst a sea of gold.

[1]  Terkel, Studs (1963). “Radio Interview with Studs Terkel, WFMT (Chicago).


  1. Avatar Lenny Schwartz April 13, 2016
    • Avatar Brett Stewart April 13, 2016
  2. Avatar William J. Burghardt May 19, 2021

Add Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Periphery Songs
Top 10 Periphery Songs
Dirty Rotten Imbeciles Songs
Top 10 Dirty Rotten Imbeciles Songs
Debbie Harry Solo Songs
Top 10 Debbie Harry Solo Songs
Carly Simon Album Covers
Top 10 Carly Simon Album Covers
15 Greatest Hits Albums With Best Unreleased Tracks & Non-Album Songs
18 Best Greatest Hits Albums With Unreleased Tracks & Non-Album Singles
Best Rock Albums Of 2022
Best Rock Albums Of 2022
12 Essential Jazz Guitar Albums
12 Essential Jazz Guitar Albums
Real Meanings Behind The Songs On Stevie Nicks In Your Dreams LP
Real Meanings Behind The Songs On Stevie Nicks In Your Dreams LP
Tom Verlaine Of Television Has Passed Away At 73
Tom Verlaine Of Television Has Passed Away At 73
Remembering David Crosby
Remembering David Crosby
David Crosby Dead At 81
David Crosby Dead At 81
Bono & The Edge: A Sort of Homecoming With Dave Letterman To Premier On Disney+ March 2023
Bono & The Edge: A Sort of Homecoming With Dave Letterman To Premier On Disney+ March 2023
10 Classic Rock Bands That Have Never Released A Live Album
10 Classic Rock Bands That Have Never Released A Live Album
Will Music CDs Become Collectors Items?
Why Basic Music CDs Will Become Collectors Items
Greatest Rock Bass Lines Of The 70s
Greatest Rock Bass Lines Of The 70s
Don Kirschner Rock Concert
Before MTV, There Was Don Kirshner’s Rock Concert
Christone "Kingfish" Ingram Interview
Christone “Kingfish” Ingram: The Interview
Garnett Grimm Of Savoy Brown Interview
Garnet Grimm of Savoy Brown: The Interview
Pat DeSalvo Of Savoy Brown Interview
Pat DeSalvo of Savoy Brown: The Interview
Steve Zing of Danzig Interview
Steve Zing of Danzig: The Interview
Real Meanings Behind Songs On Rihanna’s Good Girl Gone Bad Album
Real Meanings Behind Songs On Rihanna’s Good Girl Gone Bad Album
Real Meanings Behind The Songs On Rihanna's Music of the Sun Album
Real Meanings Behind The Songs On Rihanna’s Music of the Sun Album
Rihanna Albums
Real Meanings Behind The Songs On Rihanna’s A Girl Like Me Album
Real Meanings Behind The Songs On Stevie Nicks Rock a Little Album
Real Meanings Behind The Songs On Stevie Nicks Rock a Little Album
Beatles Albums In Order
Beatles Albums In Order Of Orignal UK And US Studio Issues
Lizzo Albums
Complete List Of Lizzo Albums And Discography
KT Tunstall Albums
Complete List Of KT Tunstall Albums And Discography
Steve Lacy Albums
Complete List Of Steve Lacy Albums And Songs