Top 5 Bob Dylan Songs

Written By: Ethan Griggs

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Born in Duluth, Minnesota in 1941 – from the Greenwich Village poster-boy, to the determined social justice warrior, to the totally tripped out literary surrealist, to the lonesome country balladeer, and all the way up to the leagues of the interpreters of the Great American Songbook – Bob Dylan has seen it all, and he has been it all. With a triple album of old standards on the way, the third volume in a series, called Triplicate, we take a look back on five of Dylan’s most crucial and iconic songs.


  • “Don’t Think Twice, It’s Alright” from The Freewheelin’ Bob Dylan (1963)

One of Dylan’s greatest abilities as a writer is being able to present two different emotions within the same song, or even just one verse of the song. On this standout track from his second album, he combines the sense of pure bitterness with the feeling of simple heartbreak and loss of a girl he once truly loved, someone who Dylan says he gave his heart to, “but she wanted my soul”. The true climax of the song comes at the last verse, one of Dylan’s most stinging sets of lyrics: “I ain’t a-sayin’ you treated me unkind/You could’ve done better but I don’t mind/You just kinda wasted my precious time/but don’t think twice, it’s alright”.


  • “The Times, They Are A-Changin’” from The Times, They Are A-Changin’ (1964)

We all know the lyrics to this song, of course, but when Dylan introduced it as part of his setlist when he played at the famous March On Washington in 1963, few people understood what a momentous piece they just heard or the influence it would have on the years to come. Dylan’s protest songs are just as relevant today as they were when he wrote them, if not more so (“Come senators, congressmen/Please heed the call”). Only time will tell what the stature of this song will be fifty years from now.


  • “Like A Rolling Stone” from Highway 61 Revisited (1965)

Dylan has said in the past that the original draft of what is far and away considered his best song was over ten handwritten pages long. How he narrowed it down to the five verses we all know and love, no one knows; but what we do know is what an astounding and influencing piece of work it was, and continues, to be. Bruce Springsteen himself said the song’s opening snare crack “sounded like somebody kicked open the door to your mind”… and Dylan hasn’t even started singing yet. The song is the classic “up one year, down another” scenario – it perfectly describes the phenomenon of falling from top of the world to the bottom of the barrel. “How does it feel?”


  • “Lay Lady Lay” from Nashville Skyline (1969)

Dylan had calmed down a bit after his mid-sixties heyday, after he had been in a motorcycle accident right after the release of his 1966 Blonde On Blonde album, but his style of writing remained imitable. Crossing over to the country world, Dylan delivered one of his best love songs with “Lay Lady Lay”, which, by that day’s standards, was considered a bit risqué… But what’s really important is the question Dylan asks in the bridge: “Why wait longer for the world to begin/You can have your cake and eat it too/Why wait longer for the one you love/When he’s standing in front of you”. The song, both in its lyrics and its aesthetic, presents an entirely different Dylan.


  • “Tangled Up In Blue” from Blood on the Tracks (1975)

If you’re a millennial, and you know only one thing about Bob Dylan, it’s probably this song. If Nashville Skyline was Dylan’s first true comeback into the mainstream, his return with this first single from his fifteenth studio album is definitely considered his second and most important one. Another classic love song, Dylan describes a relationship that is abandoned and then rekindled later in life, only to be abandoned once again. The song deals with the duality of a relationship where one person is a ramblin’ man, and the other a seemingly well off gal who eventually become a stripper, but retains all the wonderful qualities Bob once loved about her, including her love of literature – a love of which Dylan obviously relates to. A true standout of his career, to be sure.

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