Music

The Best Songs From Bob Dylan’s First 7 Albums

The Duluth, Minnesota-born songwriter and performer Bob Dylan has released dozens of albums. More than 50. Some are collections of cover songs, some are collections of spiritual songs, and many are collections of original tunes. But the artist they call The Bard earned his fame and mythical status thanks to his early releases.

When he arrived in New York City in the early 1960s, the world was changing, and Bob ended up being at the center of much of it. From the folk revival to Civil Rights to the onset of rock & roll, Dylan was somehow always involved. And all of this informed his earlier releases. But for those who want to dive in for the first time, what songs should be played first?

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We wanted to answer that very question. These are the best single songs from each of Bob Dylan’s first seven albums.

“Song to Woody” from Bob Dylan (1962)

Bob Dylan’s self-titled debut LP included mostly covers of traditional songs. His label wanted to put a fresh face on old compositions. But still Dylan was able to sneak two originals on the album, including this ode to his hero, folk singer Woody Guthrie. Want to understand Dylan’s creative roots? This is the place to begin for sure.

“Don’t Think Twice, It’s All Right” from The Freewheelin’ Bob Dylan (1962)

Dylan’s 1962 album is an all-time classic (as are many of the records on this list), and so it’s hard to choose which song is the best from it. But “Don’t Think Twice, It’s All Right” is a great choice.

Songs like “Blowin’ in the Wind” and “Masters of War” are fantastic too, but “Don’t Think Twice, It’s All Right” is just an epic breakup song that showcases Dylan’s ability to leave at any time.

“With God on Our Side” from The Times They Are a-Changin’ (1964)

Dylan’s 1964 LP, The Times They Are a-Changin’, includes the title track, which is one of history’s greatest tunes. But everyone knows that song. So, let’s take a look at another, which is just as important. The ’60s were full of conflict, and often that conflict is justified on both sides by religion. And on “With God On Our Side,” Dylan criticizes that dynamic bravely.

“It Ain’t Me Babe” from Another Side of Bob Dylan (1964)

Dylan was like the thing he sang about so often. The wind. Just when you think you know where it is or where it’s going, it changes. It’s similar to a flame—ungraspable. And this song from his 1964 LP, Another Side of Bob Dylan, is an anthem to that style of comportment. Dylan leaves, so you’re better served if you don’t stick around either. That’s what he sings about here.

“It’s Alright, Ma (I’m Only Bleeding)” from Bringing It All Back Home (1965)

It’s impossible to choose the best song from Dylan’s 1965 LP, Bringing It All Back Home. The album opens with “Subterranean Homesick Blues” and also includes “Maggie’s Farm,” “Mr. Tambourine Man,” “Gates of Eden,” and “It’s All Over Now, Baby Blue.”

But let’s focus on “It’s Alright, Ma (I’m Only Bleeding).” On it, Dylan creates a sick beat with his acoustic and almost raps over it, offering poetic, existential lyrics for the ages.

“Desolation Row” from Highway 61 Revisited (1965)

Fans of Dylan may balk at anything besides “Like a Rolling Stone” being named the best song from Highway 61 Revisited. But “Desolation Row” is so vivid and filled with such a cast of characters that it’s impossible to ignore. Sure, “Like a Rolling Stone” may be more historically significant, but “Desolation Row” is a work of art worthy of the greatest halls. Classic and original—two words that mark the best of Dylan’s work.

“Leopard-Skin Pill-Box Hat” from Blonde on Blonde (1967)

One of Dylan’s most beloved albums, Blonde on Blonde is another that boasts classic song after classic song. But instead of looking at one of his more earnest songs like “Visions of Johanna,” let’s look at a rollicking romp of a tune, “Leopard-Skin Pill-Box Hat,” on which Dylan pokes fun at those keeping up with ridiculously self-serious fashion trends.

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