Bob Dylan is one of the most acclaimed musicians of his generation, both as a performer and a songwriter, so it’s certainly not easy to extract any ten best songs from his catalog, outside of those in A Complete Unknown. He’s got an extensive discography that spans multiple decades and runs through many different genres of music, from acoustic folk, to rock-and-roll, and later to all-out rock. Dylan has several underrated albums from later in his career that deserve more recognition, but it’s widely accepted that the 1960s were the strongest period of his work.

James Mangold’s surprisingly accurate biopic A Complete Unknown follows the earliest era in Bob Dylan’s career, spanning from the release of his debut self-titled album to his controversial performance at the Newport Folk Festival. While many of Dylan’s best songs would come after this festival set in 1965, the albums that came before it contain the singles that facilitated his rise to fame in the first place.

10 “My Back Pages”

Released In 1964

“My Back Pages” is one of Bob Dylan’s most honest and introspective songs, with lyrics that discuss how his attitudes towards politics and stardom have changed since becoming the face of the folk music movement in America. The song was released on his 1964 album “Another Side of Bob Dylan”, which was his final studio album before moving away from the acoustic sound that made him famous.

What’s so powerful about “My Back Pages”, beyond the beautiful guitarwork and flawless use of empty space between verses, is the honesty of Dylan’s verses. He its that he’s not the unwavering voice of reason that he used to present himself as in songs like “The Times They Are A-Changin’,” confessing that “I was so much older then, I’m younger than that now.”

9 “It’s All Over Now, Baby Blue”

Released In 1965

“It’s All Over Now, Baby Blue” is one of Bob Dylan’s most underrated songs of all time, blending the acoustic sounds of his early career with a more progressive rock-and-roll sound that he adopted on his 1965 album “Bringing It All Back Home”. The track served as the album’s closing tune, with many fans suspecting that it’s supposed to be a conversation between contemporary Dylan and his younger self.

This was famously the final song that Bob Dylan played at the Newport Folk Festival, where he was booed off the stage for using an electric guitar instead of his classic acoustic one. This lends credence to the theory that it’s a ballad about Dylan’s own struggles leaving classic folk music behind and embracing more experimental sounds instead. Of course, it’s all wrapped up inside a more traditional love song that gives the lyrics two depths of meaning.

8 “Subterranean Homesick Blues”

Released In 1965

“Subterranean Homesick Blues” is the opening track to “Bringing It All Back Home”, and the first studio single that Dylan released after going electric at Newport. It’s a completely different sound from anything else that the singer had released up to that point, making it one of his most controversial songs at the time.

With this track, Dylan wanted to cause a rock revival that would take the world by storm just as he’d managed with folk music several years prior.

The song is a protest anthem against the gradual disappearance of rock music, with a syllabic meter that’s very reminiscent of ‘50s rock-and-roll icons like Chuck Berry. With this track, Dylan wanted to cause a rock revival that would take the world by storm just as he’d managed with folk music several years prior. It’s upbeat and catchy, but its real genius lies in the abstract lyrics that pay homage to some of the most iconic rock-and-roll beats of Dylan’s generation.

7 “Boots Of Spanish Leather”

Released In 1964

Particularly in this early period of Bob Dylan’s career, there was something about his heartfelt ballads that couldn’t be beaten. His political anthems were great, but it’s the universal love songs like “Boots of Spanish Leather” that have aged most effectively and remain firmly among Bob Dylan’s best songs.

This heartbreaking track is told from the perspective of two lovers whose romance begins to fall apart when one of them leaves for a long journey. It’s an extremely bittersweet song that makes the most of Dylan’s sardonic songwriting, somehow making these unnamed characters feel real and authentic despite revealing very little about them.

6 “One Of Us Must Know (Sooner Or Later)”

Released In 1966

“One Of Us Must Know (Sooner Or Later)” was released on Dylan’s hugely popular 1966 album “Blonde on Blonde”, which is frequently cited as the singer’s strongest project from this era of his career. The song is an extremely cinematic ballad that paints a vivid picture of an old relationship in Dylan’s life, with very honest and transparent lyrics that stray away from his usual abstract storytelling and adopt a much more straightforward approach instead.

“Blonde On Blonde” is one of Bob Dylan’s best albums, and this song perfectly encapsulates exactly what’s so addictive about this particular sound. It’s an ideal combination of his early stripped-back acoustics and his later, more orchestral instrumentals that works perfectly thanks to the quality of storytelling on display. Lyrics such as “I told you as you clawed out my eyes, that I never meant to do you any harm” paint such a visceral image of this conflicted relationship that it's impossible not to feel something when listening to it.

5 “Blowin’ In The Wind”

Released In 1963

“Blowin’ In The Wind” was released on Dylan’s second studio album “The Freewheelin’ Bob Dylan”, and it’s the perfect example of how he used his loud political voice to make folk music accessible to the masses. The song was quickly adopted by the Civil Rights movement in the early ‘60s thanks to its hopeful message of resilience and strength in the face of adversity.

The song poses a series of hypothetical questions (“how many years can a mountain exist before it is washed to the sea?”) that Dylan uses to draw allegories and metaphors about the struggles faced by the black community in 1960s America. With his powerful refrain that the “answer is blowing in the wind”, Dylan offers hope that a brighter future is on the horizon.

4 “The Times They Are A-Changin’”

Released In 1964

Released as the lead single of Dylan’s 1964 album of the same name, “The Times They Are A-Changin’” may be the singer’s most outwardly political anthem of them all. It’s another song about resilience and hope that was quickly tied to Dylan’s of the Civil Rights movement, becoming an anthem for change in contemporary America.

In the song's lyrics, Dylan warns the powers-that-be that they’d “better start swimming or you’ll sink like a stone,” cementing this as the artist’s most revolutionary and provocative track yet.

The track has since become one of Dylan’s most successful singles ever, making a major appearance on A Complete Unknown’s soundtrack and irrevocably tying itself with the evolving society of New York in the ‘60s. In the song's lyrics, Dylan warns the powers-that-be that they’d “better start swimming or you’ll sink like a stone,” cementing this as the artist’s most revolutionary and provocative track yet.

3 “Don’t Think Twice, It’s Alright”

Released In 1963

The majority of Bob Dylan’s early catalog consisted solely of vocals and acoustic guitar, so it’s surprising that he still managed to make sounds that sounded as unique and singular as “Don’t Think Twice, It’s Alright.” With its precise finger-picking guitar, this beautiful love song was originally written as a tribute to his then-girlfriend Suze Rotolo, from whom he was separated for several months.

The song is neither sad nor happy, but rather a bittersweet meditation on how love can be both painful and rewarding. It’s one of the standouts on “The Freewheelin’ Bob Dylan”, and one of the singer’s few songs that doesn’t try to hide his emotions behind witty metaphors or throwaway jokes. Lyrics like “I gave her my heart but she wanted my soul” display a level of emotional maturity on this record that make it hard to believe Dylan was barely in his 20s at the time.

2 “Like A Rolling Stone”

Released In 1965

Bob Dylan has won many awards throughout his lucrative career, but the success of his track “Like A Rolling Stone” remains his biggest accomplishment. The song is one of the most recognizable pieces of music ever written, putting Dylan’s newfound rock-and-roll style to the test. It’s not as political as his early catalog, nor as romantic as some of his deeper cuts, but the gorgeous instrumentals and anthemic hook make it an undeniable earworm.

It’s been long speculated that “Like A Rolling Stone” was inspired by the celebrity socialite Edie Sedgewick, who influenced many tracks on Dylan’s follow-up record “Blonde on Blonde”. This was never confirmed, but many of the narrator’s comments about the song’s subject line up with Dylan’s own suspected descriptions of Sedgewick on tracks like “Leopard-Skin Pill-Box Hat.”

1 “Girl From The North Country”

Released In 1963

Bob Dylan has been through so many eras of songwriting that it’s difficult to pin down any specific “best” song, as everybody is bound to have their specific preferences. However, his 1963 track “Girl From The North Country” is certainly one of his most moving, honest, absorbing, and timeless songs of all time. The track has a very simple guitar riff, but Dylan’s emotional vocal performance and rich imagery make it utterly compelling.

“The Freewheelin’ Bob Dylan” is brimming with romantic ballads like this, and many of them were inspired by the singer’s relationship with Suzy Rotolo. It’s never been confirmed that “Girl From The North Country” is one of those examples, but the raw emotion in his voice and the extremely intimate lyrics make it a very real possibility.