37 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.

“Hurricane”

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.

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