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Best 20 Bob Dylan Songs, Ranked

This songwriting Bard has proven he’s got the write stuff throughout his revered career.

The word “songwriter” somehow seems insufficient when discussing Bob Dylan, who’s won 10 Grammys and countless other awards, not to mention 2016’s Nobel Prize in Literature, an honor that truly shocked and humbled the musician. But the following Bob Dylan songs are timeless and prove the artist mastered the skill.

“If someone had ever told me that I had the slightest chance of winning the Nobel Prize, I would have to think that I’d have about the same odds as standing on the moon,” he wrote in his acceptance speech, which was delivered in his absence by Azita Raji, the U.S. Ambassador to Sweden.

Bob Dylan performs at The Bitter End folk club in Greenwich Village in 1961 in New York City
Bob Dylan performs at The Bitter End folk club in Greenwich Village in 1961 in New York City Getty

“When I started writing songs as a teenager, and even as I started to achieve some renown for my abilities, my aspirations for these songs only went so far. I thought they could be heard in coffee houses or bars, maybe later in places like Carnegie Hall, the London Palladium. If I was really dreaming big, maybe I could imagine getting to make a record and then hearing my songs on the radio. That was really the big prize in my mind. Making records and hearing your songs on the radio meant that you were reaching a big audience and that you might get to keep doing what you had set out to do.”

man with guitar
Bob Dylan (1966)Getty

He, of course, has gone on to reach a humongous audience, selling more than 145 million albums throughout his multi-dimensional seven-decade career. “The relationship you have to a song can change over time. You can outgrow it, or it could come back to haunt you, come back stronger in a different way. A song could be like a nephew or a sister, or a mother-in-law,” Dylan, now 83, told The Wall Street Journal, noting how all music, including his own creations, are bound to morph in listeners’ minds and hearts through the years.

His image and personality is just as hard to pin down. “How do you even succinctly describe him?” SPIN magazine recently asked. “Musician? Certainly. But also, artist and activist. Poet. Cultural icon. Actor. More reverential and contemptuous terms have also been used. Prophet. Anarchist. Evangelist. Judas. These titles don’t leave much space for the human, father, husband or friend.”

people performing on stage; bob dylan songs
Bob Dylan performing at Rock and Roll Hall of Fame Induction (1988)Getty

The one constant for Dylan has been his commitment to his craft. The Songwriters Hall of Fame, to which he was inducted in 1982, calls him one of the greatest icons of American music and culture, and A Complete Unknown, a biopic on the artist (born Robert Allen Zimmerman), is due next year starring Timothée Chalamet. “This might earn the ire and wrath of a lot of Bob fans, rightfully,” Chalamet revealed in a recent interview, “but [Dylan’s manager Jeff Rose] sent me a 12-hour playlist of unreleased Bob stuff from 1959 to ’64. I feel like I’m holding onto gold or something.”

Bob Dylan performing live onstage at the Singers Club Christmas party on his first visit to Britain, December 22, 1962
Bob Dylan performing live onstage at the Singers Club Christmas party on his first visit to Britain, December 22, 1962 Brian Shuel/Redferns

Fans would surely love to get their ears on those recordings, but they can find comfort in the fact that the artist can still be caught live out on the road: Dylan is headlining the 2024 Outlaw Music Festival that’s running from June through September and featuring such other artists as Willie Nelson, Robert Plant, Alison Krauss, and John Mellencamp.

To make a list of the best Bob Dylan songs is an impossible feat for an artist of his caliber, so this collection serves instead as a mere starting point for fans both old and new. Be sure to add your favorites below!

20. “It’s All Over Now, Baby Blue” (1965): Bob Dylan songs

Former flame Joan Baez, Dylan’s fan base, and the artist himself are all potential “Baby Blues,” as audiences and critics alike have long speculated to whom the artist was singing and referring to on this classic track. “You must leave now, take what you need, you think will last. But whatever you wish to keep, you better grab it fast,” he sings, and the song perfectly captures both his heated disappointment and an aching sadness.

19. “Sad-Eyed Lady of the Lowlands” (1966)

Clocking in at more than 11 minutes long, this country-tinged waltz was recorded in Nashville’s historic Studio A. “I just sat down at a table and started writing.… And I just got carried away with the whole thing.… I just started writing and I couldn’t stop,” Dylan told Rolling Stone of the tune that fills up an entire side on his Blonde on Blonde double album.

18. “Lay Lady Lay” (1969): Bob Dylan songs

This song was to have been used in the film Midnight Cowboy starring Dustin Hoffman and Jon Voight, but it wasn’t completed in time. In an interview transcript that was auctioned off in 2020, Dylan noted that he actually penned it for Barbra Streisand to perform, but not everyone is convinced Dylan recalled that correctly. Regardless, Babs was honored at the thought. “I’m very flattered,” she told NBC News at the time. “What I remember is getting flowers from him with a handwritten note asking me to sing a duet with him, but I just couldn’t imagine it then. Guess what, Bob, I can imagine doing it now!”

17. “It’s Alright Ma (I’m Only Bleeding)” (1965)

This “grim masterpiece,” according to Down the Highway: The Life of Bob Dylan biographer Howard Sounes, finds Dylan taking aim — often at a rapid-fire pace — at a string of ills in American culture, including commercialism and a war mentality. It’s reportedly one of the artist’s favorites of his own. “I’ve written some songs that I look at, and they just give me a sense of awe. Stuff like, ‘It’s Alright, Ma,’ just the alliteration in that blows me away,” he once told The New York Times.

16. “It Ain’t Me Babe” (1964): Bob Dylan songs

Another one of his bittersweet kiss-off songs (“I’m not the one you want, babe I will only let you down”), this track is said to have been inspired by his relationship with girlfriend Suze Rotolo. Another reported minor jab within it comes with his “no, no, no, it ain’t me, babe” in the lyrics: The Beatles, of course, had just scored big with their 1964 hit “She Loves You,” and its ensuing “yeah, yeah, yeahs.”

15. “Idiot Wind” (1975)

“Dylan was recording ‘Idiot Wind’ and I thought this is so powerful. When has Dylan ever been this raw? The amount of rage coming out of him was so powerful,” Glenn Berger, an engineer on the album Blood on the Tracks, shared with Mojo magazine. When Dylan finished the song in the studio, Berger adds, he waited “a few seconds and then turns to us in the control room and sarcastically says: ‘Was that since-e-e-re enough?’ Maybe it had been so powerful for him emotionally that he had to take away some of that intensity.”

14. “Girl From the North Country” (1963): Bob Dylan songs

This track was used as the name of the Broadway musical based on Dylan’s songs. After being released on 1963’s The Freewheelin’ Bob Dylan, the artist later duetted on it with Johnny Cash, and that version appears on 1969’s Nashville Skyline. “It’s got all the elements of beautiful folk writing without being pretentious,” Rolling Stone guitarist Keith Richards has said of the song, which he notes drew on traditional Anglo-Celtic music.

13. “All Along the Watchtower” (1967)

Jimi Hendrix, of course, would go on to make this a trademark song of his own. “All those people who don’t like Bob Dylan’s songs should read his lyrics. They are filled with the joys and sadness of life,” Hendrix once said, adding that “Sometimes, I play Dylan’s songs and they are so much like me that it seems to me that I wrote them. I have the feeling that ‘Watchtower’ is a song I could have come up with, but I’m sure I would never have finished it.”

12. “Knockin’ on Heaven’s Door” (1973): Bob Dylan songs

This is another gem from Dylan that’s scored big for those who remade it, most notably Eric Clapton and Guns N’ Roses. The tune, which appears in the 1973 film Pat Garrett and Billy the Kid, continues to be a simple, haunting masterpiece that seems to just get better every time one hears it.

11. “The Times They Are A-Changin’” (1965)

“I wanted to write a big song, some kind of theme song, with short, concise verses that piled up on each other in a hypnotic way. This is definitely a song with a purpose. I knew exactly what I wanted to say and who I wanted to say it to,” Dylan revealed in the liner notes for his 1985 album Biograph. The musical wakeup call seemed to take on even deeper weight, as it was released just a few months after the assassination of President John F. Kennedy.

10. “The Lonesome Death of Hattie Carroll” (1964): Bob Dylan songs

This stark tune tackles racism as it details the real-life 1963 Baltimore murder of the titular Black 51-year-old barmaid. Her killing resulted in a mere six months of jail time for William Zantzinger, a 24-year-old white man from a wealthy family and “the person who killed for no reason, who just happened to be feelin’ that way without warnin’.” Though some details were inaccurate, the bulk were true, and, as The Guardian notes, “the fact that [Dylan’s delivery is] measured, unhysterical and unsentimental in tone makes it all the more impactful.”

9. “Desolation Row” (1965)

“‘Desolation Row’ is so simple musically — just three chords for 11 minutes, with minimal accompaniment – yet it’s so effective,” Mick Jagger once explained to Rolling Stone of this song in which “famous people surrealistically appear, some of them mythical and some of them real. The Phantom of the Opera. Ezra Pound and T.S. Eliot. Cinderella. Bette Davis. Cain and Abel.… It’s a wonderful collection of imagery — a fantasy Bowery — that really gets your imagination working.”

8. “Positively 4th Street” (1965): Bob Dylan songs

Yes, I wish that for just one time you could stand inside my shoes. You’d know what a drag it is to see you.” It’s believed the targets from Dylan’s poisonous pen on this one were the fake and jealous fellow artists the singer knew during his days in Greenwich Village. Their grief and hassle, at least, had a musical payoff even beyond this song’s success: “There came a point when I heard a Dylan song called ‘Positively Fourth Street’ and I thought ‘Oh my God, you can write about anything in songs.’ It was like a revelation to me,” Joni Mitchell once noted of how it led to her future success.

7. “Visions of Johanna” (1966)

As American Songwriter once put it, this “is a song that captures the feeling of being pushed to the edge of an emotional brink. It’s 4 AM in your soul, ‘last call’ at the bar of salvation, and you’re in the mood for one more drink.” The artist once shared with 60 Minutes that a lot of his lyrics seemed “almost magically written,” and this take on the intricacies and contradictions of love and attraction is beautifully rife with imagery — and mystery.

6. “Mr. Tambourine Man” (1965): Bob Dylan songs

“Bob’s lyrics were exquisite. ‘To dance beneath the diamond sky with one hand waving free’ – that was the line that got me. I think he was finding himself as a poet,” David Crosby told Rolling Stone of this classic, which was also a big hit for Crosby’s The Byrds. “Bob did not envision this song the way we did it.… I think hearing our version was part of what made Dylan shift over to being a rocker. He thought, ‘Wait a minute, that’s my song,’ and he heard how it could be different.”

5. “A Hard Rain’s A-Gonna Fall” (1963)

“Every line in it is actually the start of a whole song,” Dylan has said of this protest tune. “But when I wrote it, I thought I wouldn’t have enough time alive to write all those songs, so I put all I could into this one.” Though it was penned in the wake of the Cuban Missile Crisis, the artist noted in his Chronicles: Volume One memoir that the piece spoke about things well beyond that specific confrontation. “After a while you become aware of nothing but a culture of feeling, of black days, of schism, evil for evil, the common destiny of the human being getting thrown off course. It’s all one long funeral song.”

4. “Tangled Up in Blue” (1975): Bob Dylan songs

This classic cut was recorded in the period following Dylan’s separation from his future ex-wife Sara, and it appears on his album Blood on the Tracks. “A lot of people tell me they enjoyed that album. It’s hard for me to relate to that — I mean, people enjoying that type of pain,” Dylan once noted on a radio show. The music site Albumism insists it “remains one of Dylan’s surrealistic tours-de-force,” and one that Dylan has often said took him “10 years to live and two to write.”

3. “Subterranean Homesick Blues” (1965)

Look out, kid!” Thrilling some and alienating others, Dylan went electric with this now-iconic stream-of-consciousness hit, his first to hit the Top 40 here in the U.S. Its success even reportedly made John Lennon worry that the Beatles would never match it. In the song, Dylan pulls from Woody Guthrie, Chuck Berry, and Beat poetry influences, and its visual clip from D.A. Pennebaker’s 1967 documentary Bob Dylan: Dont Look Back is as iconic as the song. “It was an idea that Dylan had in a bar one night, and I thought it was a terrific idea,” the director told Sound & Vision, “so we brought along all of those sharp cardboards. Joan Baez wrote out some of them; Donovan did a ton of them.” No cards survived, however. “I don’t have any of them now. They got blown all over London, when we tried to do it on the roof,” Pennebaker shared.

2. “Blowin’ in the Wind” (1963): Bob Dylan songs

“I realized he was a genius turning out one great song after another. ‘Blowin’ in the Wind’ is still one of the greatest songs of the 20th century,” folk legend Pete Seeger told Mojo, with Mavis Staples adding that the tune — with its themes of peace, freedom, and equality — impressed her and countless other artists, too. “I fell in love with it because of the message,” she noted of the song, which borrows the medley from the Civil War-era spiritual “No More Auction Block for Me.” “[And] when Sam Cooke heard ‘Blowin’ in the Wind’ he said, ‘Now if a young white guy can write a song like that then I got to get my pen in hand.’ And that’s when he wrote ‘A Change Is Gonna Come.’”

1. “Like a Rolling Stone” (1965)

Dylan’s highest charting single reached No. 2 and it remains one of his most lauded works. “Bob Dylan’s sneer on ‘Like a Rolling Stone’ turns the wine to vinegar,” U2’s Bono told Rolling Stone of the song that finds the artist “[baring] his teeth at the hipsters, the idea that you had a better value system if you were wearing the right pair of boots.”

Dylan told Montreal’s CBC Radio that it all came from “this long piece of vomit, 20 pages long” that he boiled down to a little over six minutes, which still impresses artists to this day. “‘Like a Rolling Stone’ feels like a torrent that comes rushing towards you. Floods your soul, floods your mind. Alerts and wakes you up instantaneously to other worlds, other lives. Other ways of being,” Bruce Springsteen told the BBC. “It’s perhaps one of the most powerful records ever made.”

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