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Bob Dylan Songs Ranked

A legendary artist who wrote time-travelling songs that hold relevance in any decade. Bob Dylan is one of many who paved the way of modern music. He set the stage for posing poetry with a guitar, and at the same time, he’s not afraid to call a calamity a new hit record. Here is a list of the Top Ten songs ranked by Roots Magazine!

#10-’Tangled Up in Blue’

Blood on the Tracks (1975, Columbia)

“Tangled Up in Blue” is one of the most honest love ballads, you can hear Dylan spill his heart in every rendition--and there are many. One important thing to note is that Dylan often uses ‘love’ and ‘blue’ interchangeably. The story he tells is about two love-lost people orbiting in opposite directions. The stars align when they meet, but it’s only for a brief gasp of moment. The song ripples with residual feelings, two chords on a constant loop, as listeners feel Dylan conjuring up a memory that casts a wicked love spell.

#9-I Shall Be Released

Music from Big Pink (1968, Capitol)

It’s been interesting to see how this song has evolved over time; originally it was a very slow and brooding melody that grew more faced paced throughout its years. Its meaning can be absorbed in many ways, as most of his songs are. But in its most literal interpretation, it’s a glimpse of someone waiting for freedom behind bars. With his cultish following, he turned it into an anthem that shook the walls down. Cutting all the fluff lines out, every word in it had reason to be spoken. But in its infancy, it wasn’t supposed to be a rallying song; it was purposefully made with a chord sequence that trudged in the mud.

#8-Rainy Day Women #12 & 35

Blonde on Blonde (1966, Columbia)

This is the opening song of his debut double album, a blues tune with a continuous marching beat and a trombone toot to match. “A long haired mule and a porcupine” was the working title, until Dylan chose the current name, based off of the Book of Proverbs 27:15: “A continual dripping on a very rainy day and a contentious woman are alike.” With the piano keys dancing happily in the background, the lyrics have an ironically grim message up until the double entendre: “Everybody must get stoned.” Some people question whether or not it was worth recording--but it obviously had some worth, it received #2 ranking in the charts.

#7-Like A Rolling Stone

Highway 61 Revisited (1965, Columbia)

“Like A Rolling Stone” is a restless slap in the face to those who thought themselves better than anyone. Dylan turned lemons into more lemons on this one, sour to the core. This song was based on a short story of his that was about a debutant beauty queen who was suddenly kicked to the curb. Every exasperated scream carries that flammable emotion. Equating his subject to nothing, Dylan uses every synonym he can to convey that message. It’s a riot of a song, one that everybody loves because it calls out classicism for the arbitrary sinkhole that it is.


Desire (1975, Columbia)

Some of Dylan’s most exciting instrumentalism is found in “Hurricane,” featuring Scarlet Rivera’s beautifully violent breaks of violin. With the whirlwind of strings and the downpour of percussions, it served perfectly as the opening track of its album. It tells a riveting story about the former boxer, Rubin Carter, who was wrongly convicted for a triple homicide but was imprisoned for 19 years. Dylan had met with him in person and connected with him on a philosophical level. Dylan felt obligated to write a song in protest, and some people consider it to be one of his best hits.

#5-Knockin’ on Heavens Door

Pat Garrett & Billy the Kid (1973, Columbia)

Here we have a song set in an interesting perspective: a sheriff on his deathbed. It was originally written for Pat Garrett And Billy The Kid, a classic Western film from 1973. Rarely ever did Dylan allow fellow artists to incorporate their own in his songs, this one was an exception. In 1966, Ted Christopher added lyrics about the Dunblane massacre--his version ranked a solid #1 in the UK.

#4-Visions of Johanna

Blonde on Blonde (1966, Columbia)

“Ain't it just like the night to play tricks when you're tryin' to be so quiet?” This song opens with a sublime line that immediately hooks the listener for more. Although Dylan has made the claim that he has never written a “drug-song,” “Visions of Johanna” was the beginning of Dylan’s head-scratching lines of psychedelic imagery.

#3-Blowin’ In The Wind

The Freewheelin’ Bob Dylan (1963, Columbia)

One of the most intimate songs of his is “Blowin’ In The Wind.” It’s heartfelt poeticism resonates with everyone who follows the lyrics line by line. Some recordings of this have a heavy guitar sound that dominates the vocals, almost like the wind blowing too loud for you to hear the depth of his inquisitions. Other recordings have the vocals as the main attraction, so the lyrics can be held on to with every breath. The meaning is simply put: we are oblivious to the beautiful world we were given and the horrifying nightmares we’ve created. This accurate portrayal of humanity is shockingly disheartening and aspiring at the same time, a recurring mood in Dylan’s work.

#2-Mr. Tambourine Man

Bringing It All Back Home (1965, Columbia)

Dylan had sleeplessly insisted that this song was based on a fellow folk musician, Bruce Langhorn, who actually did carry a tambourine with him sometimes. Most people write it off as a drug-induced coma. But some suggest that it was inspired by Arthur Rimbaud, an emerging French poet at the time it was written.

#1-The Times They Are a-Changin’

The Times They Are a-Changin’ (1964, Columbia)

A timeless classic that still calls its listeners to action to this day. Dylan uses a very unique time signature that is best heard through the guitar playing. It creates more emphasis on certain words that you can hear Dylan drag out. If Dylan wasn’t quite sure people heard the lyrics, he made sure to play they’re heart strings with that sharp hitting harmonica.

Written by Ashley Cantrelle


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