37 Best Bob Dylan Songs

“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.