37 Best Bob Dylan Songs

Best Bob Dylan Songs

Since 1961, Bob Dylan has released 39 studio albums, received a Presidential Medal of Freedom, a Nobel Prize for Literature, and has taken his place in the Rock and Roll Hall of Fame.

He’s been called “the voice of his generation,” “Judas,” and the “most influential songwriter ever”.

Keep reading for a list of the best Bob Dylan songs you’ll find.

“Mr. Tambourine Man”

Song year: 1965

Dylan wrote “Mr. Tambourine Man” and released it on his album Bringing It All Back Home. Other bands often covered Dylan’s songs and made them famous. The Byrds covered this and brought it to #1 on the US and UK charts.

With a pied piper feel, the lyrics describe someone caught up in the music of a traveling musician. The music takes the song’s speaker and the listener on a literal and metaphorical journey.

“Like a Rolling Stone”

Song year: 1965

“Like a Rolling Stone” from Highway 61 Revisited often appears in lists as Dylan’s best song. It is undoubtedly one of his most iconic. It was also his first big hit, making it to #2 on the US charts.

The song describes a debutante’s fall from society and wealth. The tone of the lyrics shows some vitriol towards people who don’t know what ordinary people go through. She started at the top. Now she’s at the bottom. Even though she once had everything, how much did she have if it could disappear instantly?

“Blowin’ in the Wind”

Song year: 1963

Dylan claimed to have written “Blowin’ in the Wind” off of The Freewheelin’ Bob Dylan in a ten-minute spurt one day. This song has gone down to be one of Dylan’s most covered songs. The most famous version was the folk group Peter, Paul, and Mary. The trio even performed the song with Dylan at the Newport Folk Festival in 1963.

“Blowin’ in the Wind,” asks a series of unanswered questions about humanity and society. While Dylan said it wasn’t a protest song, the lyrics show strong opinions about war, civil rights, and empathy.

“Girl From the North Country”

Song year: 1963

The original version of Dylan’s English ballad-inspired “Girl From the North Country” appeared on The Freewheelin’ Bob Dylan. However, it also appeared as an essential, if a little awkward duet with Johnny Cash on Dylan’s 1969 Nashville Skyline.

In this song about a lost love, the singer urges the listener to keep an eye out for his once-true love. He wants to make sure she’s doing all right and that she hasn’t changed. He still cares for her, but he also seems to love the memory and nostalgia of her. He might have regrets, and he might miss her, but he’s not looking for her himself.


Song year: 1976

“Hurricane” from the album Desire tells the real-life story of Rubin “Hurricane” Carter, a boxer jailed for murder. Many, including Dylan, believed him to be innocent. To bring awareness to Carter and help his plight, Dylan wrote this song and raised money for Carter’s defense during his 1975 Rolling Thunder Revue tour.

There were all sorts of problems with the case against Carter, and in 1985, he and his friend John Artis, also convicted of the crime, were exonerated. Carter ended up spending 19 years in prison for a crime he didn’t commit.

“The Times They Are A-Changin’”

Song year: 1964

While Dylan wrote topical songs about political and civil rights issues, his songs about political and social distress and change with the longest legacy are influenced by the time he wrote them but have general enough lyrics. They can apply to a multitude of times and situations.

“The Times They Are-A Changin’,” from the album of the same name, was influenced by civil rights and by an emerging counter-culture of youth who were tired of old closed ways the country was being run and were ushering in new ideas.

While specific issues change, this song has held up generation after generation as the ideas and progressiveness of the youth push against the status quo of their elders.

“Don’t Think Twice, It’s All Right”

Song year: 1963

In a world of sweet love songs, Dylan released the unsweet, anti-love song, “Don’t Think Twice, It’s All Right,” on The Freewheelin’ Bob Dylan. Dylan wrote this after his girlfriend, Suze Rotolo, pictured on his arm on the album’s cover, left him to study in Italy.

This song functions as a sort of aubade, a parting of lovers at the break of dawn. The song’s speaker is leaving his lover before she can leave him. He is hurt and bitter, voicing his dissatisfaction with her and their relationship.

While this is an angry song, it’s honest and captures how many people feel at the end of a relationship.

“Lay, Lady, Lay”

Song year: 1969

Off of Nashville Skyline, “Lay, Lady, Lay” is a sexy song of lazy seduction. The singer is inviting his woman to stay with him in his bed. Something is relaxing and comfortable about this song. If it is manipulative, it’s only because he loves her and wants her to choose him and be with him.

Dylan had intended this for the movie Midnight Cowboy, but the song wasn’t ready in time. Even if it had been, it wasn’t a good fit for the film. It still hit #7 in the US charts, which is not bad for a song about a lazy day making love in bed.

“Shelter From the Storm”

Song year: 1975

“Shelter From the Storm” comes from Blood on the Tracks, the album Dylan worked on while his marriage with his first wife, Sara, ended. Many of the songs on the album capture friction between a couple.

“Shelter From the Storm” is about a caring relationship full of grace and loving emotions without commitment or seriousness. The song’s speaker didn’t realize what he had. He didn’t understand what her love was. He is grateful for her, but her love is gone now. He believes he’d do things differently if he had the chance.

“A Hard Rain’s A-Gonna Fall”

Song year: 1963

So many of Dylan’s songs work because they are full of mythological images, archetypes, and symbolism that resonate with people at a deep level. “A Hard Rain’s A-Gonna Fall” from The Freewheelin’ Bob Dylan is a song warning about war in an album with many songs about war being destructive for ordinary people.

Dylan took the structure from this one from an old folk ballad known as “Lord Randall,” a standard song folk singers of the time drew from.

This song imagines a post-nuclear war world full of painful sights and worries about what the younger generation is inheriting. It is a call to action and a warning.

“It Ain’t Me Babe”

Song year: 1964

“It Ain’t Me Babe,” off of Another Side of Bob Dylan, wanders away from the political realm of Dylan’s earlier albums and into the personal.

The song’s speaker either breaks up with a lover or rejects a would-be lover. He is honest. It might not be nice, but it’s not mean either. He knows they’re not right for each other, so he’s stopping things before they get messy.

It’s about knowing yourself and not wasting anyone’s time in a relationship that you know is doomed to fail.

“It Ain’t Me Babe” has been successfully covered by The Turtles, Joan Baez, Johnny Cash, Johnny Thunders, and Peter, Paul, and Mary.

“Subterranean Homesick Blues”

Song year: 1965

Bob Dylan has a reputation for writing songs jammed-packed with lyrics. “Subterranean Homesick Blues” from Bringing It All Back Home triples down on this reputation in a rapid-fire succession of cultural references alluding to social and political unrest and the tone of the times.

The black and white video of Dylan flipping through giant cue cards while Beat poet Allen Ginsberg wanders in the background amidst the city’s scaffolding is brilliant and iconic.

“Rainy Day Woman #12 & #35”

Song year: 1966

Despite the lyrics, Dylan has insisted the mysteriously titled “Rainy Day Woman #12 & #35” from the double album, Blonde on Blonde, is not about drugs.

This song, which sounds like a crazy parade, seems to be about nothing a person does ever being good enough, whether in a relationship, a job, society, or anywhere. You just can’t win.

“Visions of Johnanna”

Song year: 1966

The epic “Visions of Johanna” is a mysterious and emotional song about a failed relationship and a lost lover that haunts you so that you see it everywhere.

No one knows who the named characters in the song are, but some have speculated that Johanna refers to folk singer and ex-girlfriend Joan Baez.

No matter who it’s about, this seven-and-a-half-minute song takes you on a tour through sorrow.

“Just Like a Woman”

Song year: 1966

Yet another one from fan and critic favorite Blonde on Blonde. It’s another of Dylan’s songs that seems to be about someone in particular from his life, but no one knows for sure, and he has not let the cat out of the bag.

“Just Like a Woman” came under fire for lyrics that could be seen as misogynistic. However, a deeper interpretation is that what Dylan is doing here portrays a woman who is so composed, mature, and grown-up but falls apart and becomes weak when she is hurt.

Of course, the song’s singer knows this secret about her because he hurt her and saw it firsthand. Still, this song is more of an indictment of that part of her character rather than an apology for how he treated her.

“Tangled Up in Blue”

Song year: 1966

The rollicking “Tangled Up in Blue ” from Blood on the Tracks is a nonlinear road song of a life. It’s about being caught up in sadness, sorrow, and failure, whether it’s yours or that of the people closest to you.

Dylan has played with this song a lot, often recording and performing different versions of the lyrics and changing first person to third and vice versa. Just like the timeline in this song isn’t fixed, neither is anything else about it.

“Forever Young”

Song year: 1974

Dylan recorded “Forever Young” with The Band for the album Planet Waves. Dylan had four children by that time, and they inspired this tender song about a parent’s wishes for his child.

Another one with quite a legacy, “Forever Young,” has been covered by Joan Baez, Diana Ross, The Pretenders, and Meat Loaf. It was also used as the theme song for the 2010-2015 television show, Parenthood.

“It’s All Over Now Baby Blue”

Song year: 1965

“It’s All Over Now Baby Blue” is another of Dylan’s not-so-fond farewell songs. The lyrics are beautiful but often cryptic, especially since no one knows who Dylan wrote this about. Whoever it was, it seemed like they had a lot going on, and Dylan, or the song’s narrator, was not up for all that.

“I Want You”

Song year: 1966

“I Want You” from Dylan’s Blonde on Blonde is a relatively short song for him, but it is nevertheless chock full of his trademark archetypal characters, which makes it so fun to sing along with.

At its core, this one is about pursuing a relationship with someone despite a million obstacles.

“Love Minus Zero / No Limit”

Song year: 1965

More than many songwriters, Dylan is a poet. “Love Minus Zero / No Limit” takes a tour of an almost historical seeming town to describe his love as strong, quiet, and intelligent, but also as someone who is broken and in need of his care.

Dylan married Sara Lownds the same year this was recorded and released, leaving most Dylan scholars to conclude that this song, which Dylan wrote while living at the famous Chelsea Hotel, was written for her.

“My Back Pages”

“My Back Pages”

Song year: 1964

With the album Another Side of Bob Dylan, Dylan was trying to move away from the pigeon-holed image of himself as a political and topical songwriter.

“My Back Pages” is Dylan rebelling against the idealism of his earlier days and the hypocrisy he came to see there. The song talks about how people lighten up and become more themselves through age and experience.

“She Belongs to Me”

Song year: 1965

This gentle song is a calming contrast to many of the hyper songs on Bringing It All Back Home. Big surprise, but no one agrees who the “she” of the song is though some fingers have been pointed at Joan Baez, Nico, and Caroline Coon. Of course, it could have been inspired by all of them or no one at all.

“She Belongs to Me” is about a woman who belongs only to herself. There is a sense of untouchable love and almost worship here.

“One More Cup of Coffee (Valley Below)”

Song year: 1976

The story goes that Dylan wrote “One More Cup of Coffee (Valley Below) while leaving a celebration in France. Before he left, someone asked him if he needed anything. He asked for a cup of coffee and held it while watching the sea below. The lyrics started writing themselves in his head.

This layered and string-heavy song is about someone taking a shot of reality and leaving before getting involved with someone who is probably in trouble.

“Sad Eyed Lady of the Lowlands”

Song year: 1966

The identity of the woman who inspired “Sad Eyed Lady of the Lowlands” from Blonde on Blonde is pretty clear. If you look at the letters in the title, you can pick out the name Sara Lownds. Also, in the song “Sarah” from Blood on the Tracks, there is a line where Dylan talks about writing this song for her at The Chelsea Hotel.

So many lyrics pack into this nearly 11-minute song about someone hard to get to know, with walls that are hard to breach. There is a lot of respect, admiration, and love throughout this song, even in moments that could read as cold.

“One Too Many Mornings”

Song year: 1964

From The Times They Are A-Chanin’, “One Too Many Mornings” is about a broken relationship where the couple cannot see eye to eye.

It’s a lovely and musically sparse song about people meeting while passing each other. They’ve tried to stay, and they’ve been through a lot, but they’ve gotten nowhere, and it’s time for each of them to keep moving on their own.

“Chimes of Freedom”

Song year: 1964

“Chimes of Freedom” appeared on Dylan’s 1964 album Another Side of Bob Dylan, which showed Dylan beginning to double down on the intricate and the personal.

Essentially “Chimes of Freedom” uses a lightning storm as an emotional release for the injustice suffered by oppression. Each strike of lightning is like the strike of a bell, in notation and tribute to the maltreated.

“With God On Our Side”

Song year: 1964

From The Times They Are A-Changin’ is the evergreen “With God On Our Side.” You could make a case for this as a political or religious song. It certainly has both elements to it, relying on the image of God and the issue of war.

However, at its core, this is a philosophical song that begs the listener to think critically and to recognize that in each disagreement, both sides believe they are the right one, the one who is justified. God might back both sides.

And anyway, if God was going to be someone’s cheerleader, wouldn’t it be humanity? Wouldn’t he choose to stop war, stop fights, stop hurting?

“Idiot Wind”

Song year: 1975

With songs like “Don’t Think Twice, It’s All Right,” we’ve already seen that Dylan can be callous and even mean. In “Idiot Wind” from Blood on the Tracks, the lyrics are savage and cruel.

Dylan was going through a separation at divorce at the time, so obviously, a lot of dark feelings were running through his veins, and perhaps this was the one way he had to exorcize them.

The lyrics place most of the blame for this broken relationship on the other party. However, in the end, the singer takes a tiny sliver of responsibility for their failed relationship.

If you need a song to listen to sometimes when you’re angry at someone, this is the perfect one. Picture their face in your mind and unleash.

“Knockin’ on Heaven’s Door”

Song year: 1973

Guns N’ Roses did a cover version of “Knockin’ on Heaven’s Door” for their album, Use Your Illusion II. However, Bob Dylan wrote this one for the movie Pat Garrett and Billy the Kid, and it was first released on the movie’s soundtrack.

Written for a Western, this song is sung from the perspective of a dying sheriff. While the lyrics are poetic, there is no great mystery as to what they’re about. The character recognizes his time is up, and he’s trying to make peace with it.

“Ballad of a Thin Man”

Song year: 1965

“Ballad of a Thin Man” is a Dylan critic’s and Dylan fan’s darling. It’s from Highway 61 Revisited. This one feels almost like a reverse blues song, the music reaches down low to dredge up anger and a sense of injustice, but it feels more predatory than expressive.

Theories about this song abound, but it is a song critical of the media and a specific journalist. Dylan’s irritation with the press wasn’t exactly a secret, and he describes this thin man as a tourist walking through sideshow imagery. He doesn’t know what’s going on, but it’s his job to pretend he does, to define what he doesn’t understand.

“Boots of Spanish Leather”

Song year: 1964

In “Boots of Spanish Leather,” Dylan returns to the influence of the traditional English ballad Scarborough Fair for a personal song that sounds like it’s centuries old.

This song describes a couple of lovers. The woman has gone to Spain, unsure when she’ll be back. The man is holding out hope and can’t wait until she returns. The lyrics follow a dialogue between the two characters.

When the man realizes his lover isn’t coming back, he asks her for a pair of Spanish boots as a souvenir to keep her in his memory. She obliges. He gets his boots, but we all know what boots were made for.

“It’s All Right, Ma (I’m Only Bleeding)”

Song year: 1965

“It’s All Right, Ma (I’m Only Bleeding)” is one of several songs from Bringing It All Home that attacks capitalism and commercialism. This lyrically dense song paints a country or world that lies to its citizens and feeds them a fake image of reality while setting up a system ensuring their failure.

The narrator here lets his mother know that he’s doing as well as anyone could in these kinds of circumstances. He is aware now of what’s going on. He’s wounded but not fatally injured by it.

“The Lonesome Death of Hattie Carroll”

Song year: 1964

“The Lonesome Death of Hattie Carroll” appeared on Dylan’s The Times They Are A-Changin. It tells the real-life story of barmaid Hattie Carroll’s murder at the hands of a wealthy young man, William Devereaux Zantzinger.

Carroll was black, and Zantzinger was white. He was convicted of manslaughter in her death and was given a six-month jail sentence.

The purpose here was to illustrate hatred, racism, and racial injustice. Dylan crafted the lyrics to create an emotional connection with his audience, to make them angry, and to make them grieve. It was effective.

“All Along the Watchtower”

Song year: 1967

If it’s not apparent by now, Bob Dylan’s songs have been covered a lot. Sometimes the cover versions sell more singles and chart higher than the original, but it’s arguable if the song was better for it.

When Jimi Hendrix recorded and released his cover of “All Along the Watchtower” with 1968’s Electric Ladyland, the song became his. Even Dylan changed how he played it after hearing Hendrix’s version. If you meet someone who swears they’ve never listened to a Dylan song, ask them about this one.

Using the archetypes of a joker and a thief, this song talks about changing society from the inside out.

“Positively 4th Street”

Song year: 1965

Dylan released “Positively 4th Street” as a single between Highway 61 Revisited and Blonde on Blonde and featured it heavily on his famous 1966 tour. The song, however, didn’t appear on either album.

The lyrics describe fake people and false friends within a community. The song ends with the narrator wishing the person he’s talking about could see how phony and pathetic he is.

“Leopard Skin Pillbox Hat”

Song year: 1966

“Leopard Skin Pillbox Hat” is a fun, bluesy number from Blonde on Blonde.

It talks about a lover/ ex-lover who buys this tacky, out-of-fashion hat. She’s trying to cultivate an image, pretending to be something she’s not, but she’s so out of touch that she can’t even get it right. Others can see straight through her, and while she does attract attention, it’s not the kind she wants.

“Murder Most Foul”

Song year: 2020

The last song in this list is the only one that does not come from the 60s or 70s, when Dylan was ever-changing but at the top of his musical and lyrical game.

“Murder Most Foul,” from the album Rough and Rowdy Ways, was first released to the internet on March 27, 2020, during the still-early days of the COVID-19 pandemic, when many people were stuck at home during the lockdown.

The subject of “Murder Most Foul” is the assassination of JFK. It’s not really about how Kennedy was killed, but the why.

This song is Dylan going back to peak Dylan form. He guides the listener through a tour of American music history, showing us how music connects people, especially when going through a nationwide event.

This song also tells us that everything, a president, a chart-topping band, and all of us, serves a purpose and is replaceable.

Top Bob Dylan Songs, Final Thoughts

Not everyone is a Bob Dylan fan. His personality can be rough and eccentric, and his voice is not everyone’s cup of tea. But Dylan, more than arguably anyone else in American music, has created a legacy of capturing complex emotions and thoughts through carefully crafted lyrics.

Plunging into Dylan’s back catalog is like falling head first into a gold mind. There is a lot to process—dirt to sift through. But in the end, it is worth it, and you end up richer for the experience.

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