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Bob Dylan Popular Song Rankings [2026]

That he is both a musician and a poet is evident from his winning the Nobel Prize in Literature in 2016.

During the Vietnam War, his songs were sung across the United States.

This time, we’ve selected some of his popular songs that have been loved for decades.

Presented in ranking format.

Bob Dylan Popular Songs Ranking [2026] (21–30)

DignityBob Dylan29rank/position

This is a song where Bob Dylan’s smoky, dandyish vocals pair perfectly with the gentle piano melody.

It also features that signature “Dylan touch,” making it a track that really feels like Dylan.

I’ve heard it was used as an insert song in an American TV drama.

Dreamin’ of YouBob Dylan30rank/position

Bob Dylan – Dreamin’ of You (Official HD Video)
Dreamin' of YouBob Dylan

Literally translated, the title would be “Dreaming of You.” The music video features Bob Dylan wandering around searching for something, and it has a narrative quality.

It’s a slow-tempo song with a mysterious melody that sticks in your head.

Bob Dylan Popular Song Rankings [2026] (31–40)

Girl from the North CountryBob Dylan31rank/position

Girl from the North Country – Bob Dylan
Girl from the North CountryBob Dylan

Bob Dylan’s “Girl from the North Country” is the perfect song for the season when cold, wintry winds blow.

Released in 1963, this classic is featured on his early masterpiece “The Freewheelin’ Bob Dylan,” which reached number one on the UK charts.

The sound of the acoustic guitar paired with Dylan’s distinctive vocals evokes a sense of poignancy and melancholy.

When he won the Nobel Prize in Literature in 2016, a musical was staged that used 20 of his songs, including “Girl from the North Country.”

Girl from the North Country (ft. Johnny Cash)Bob Dylan32rank/position

Bob Dylan with Johnny Cash – Girl from the North Country (Official Audio) ft. Johnny Cash
Girl from the North Country (ft. Johnny Cash)Bob Dylan

Recorded in February 1969 and opening the album Nashville Skyline that April, this song is a historic duet by Bob Dylan and Johnny Cash.

Originally a folk ballad included on the 1963 masterpiece The Freewheelin’ Bob Dylan, it was reborn with a richly country-infused sound through its re-recording in Nashville.

The lyrics depict a narrator thinking of a former lover living in the North Country and praying for her happiness from afar; the contrast between the two singers’ voices elevates a personal reminiscence into a universal sense of nostalgia.

It was also included on the soundtrack of the 2012 film Silver Linings Playbook, reaching a new generation.

It’s a song I highly recommend for quiet winter nights or while traveling, and for anyone interested in the fusion of folk and country.

Have Yourself a Merry Little ChristmasBob Dylan33rank/position

Bob Dylan – Have Yourself a Merry Little Christmas (Official Audio)
Have Yourself a Merry Little ChristmasBob Dylan

Bob Dylan, a musician from the United States who is also popular in Japan, is known for his distinctive, gritty voice.

Surprisingly, however, his singing style is gentle and enveloping.

One example is his Christmas song “Have Yourself a Merry Little Christmas.” While his voice creates a sense of power, the vocal line itself is simple, with little inflection and few high notes, making it very easy to sing.

He Was a Friend of MineBob Dylan34rank/position

A poignant folk song that captures the pain and sense of loss from a broken friendship.

Bob Dylan’s distinctive vocals convey the sorrow of losing a close friend with unflinching honesty.

Released in 1962, the piece has been widely interpreted as a response to President Kennedy’s assassination, and Dylan himself has said as much.

It has been covered by many artists, including the Grateful Dead and Willie Nelson, and was featured in the 2005 film Brokeback Mountain.

Recommended for anyone who has lost someone dear or wishes to reflect on the value of friendship.

He not busy being born is busy dyingBob Dylan35rank/position

[Moving Quotes] A Collection of Quotes That Can Change Your Life in an Instant: 8 Short English Quotes
He not busy being born is busy dyingBob Dylan

“Those who aren’t busy being reborn every day are busy dying every day.” Does it mean we should live today to find a self that’s different from yesterday? It makes me feel as if I’m being asked whether I’m taking a negative or a positive view.