Starting your Bob Dylan musical library

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I’ve been mulling this over for a while. If you were to start a Bob Dylan musical library, how would you do it? There are over forty albums, plus all sorts of illegal bootlegs. Rather than just say “start with these twenty,” I wanted to deal with a more manageable number. After weeks of consideration, mostly while I was driving, this is what I came up with. It’s “one per decade plus another for the Sixties.”

There are many variations on this and some might complain that I’ve skipped important eras such as the late Seventies/early Eighties Christian era. All things in their time. Once I’ve established this initial list, we’ll branch out from here, looking at albums that are either close in time to these or else not otherwise represented.

This list does not include all the albums that I would consider masterpieces, but it’s a start. If you don’t have any of these, I would recommend you get them in the chronological order listed. Things to which you should pay attention: lyrics (always), simplicity or complexity of musical arrangement, quality of voice, and overall album consistency. I’ve included some free form comments after each album.

Thanks to my daughter Katie, the best Dylanologist I know, for her input on this, though any errors and opinions are mine alone.

The Freewheelin’ Bob Dylan (1963)

Bob Dylan album cover

Second album, first masterpiece. All songs are now classic but particularly note “Blowin’ in the Wind,” “Masters of War,” “A Hard Rain’s A-Gonna Fall,” and “Don’t Think Twice, It’s All Right,” and that’s just half way through the album. That’s Suze Rotolo on the cover with Dylan in Greenwich Village in New York City.

See the Wikipedia entry for the album. [Amazon]

Highway 61 Revisited (1965)

Bob Dylan album cover

Yet another masterpiece, perhaps the best of them, and only two years after Freewheelin’. Rolling Stone magazine named the song “Like a Rolling Stone” its number one song of all time. This album features the electric blues guitar of Mike Bloomfield. Dylan has said that he regrets that he couldn’t get Bloomfield for later albums. He also jokingly suggested that “Desolation Row” should be the new national anthem.

The album is squarely in the middle of the whole acoustic-folk-to-electric-rock controversial period for Dylan that is documented in the video No Direction Home.

See the Wikipedia entry for the album. [Amazon]

Blood on the Tracks (1975)

Bob Dylan album cover

For many people, this was Dylan’s first “hit album” since Blonde on Blonde in 1966, but that’s skipping over a lot of excellent work that I’ll get to in future entries in this series. If you don’t own the album, you have probably at least heard the opener “Tangled Up in Blue,” “Shelter from the Storm,” as well as Joan Baez’ cover of “Simple Twist of Faith.”

The song “Idiot Wind” stands out as one of the best put-down songs (perhaps mutual), along with Dylan’s single “Positively 4th Street” that’s on Biograph, a collection from 1985. (4th Street is in New York City in Greenwich Village.)

Much of this album was recorded twice, once in New York City and then again in Minneapolis, with the final album primarily from the latter sessions. I’m told that the bootleg album Blood on the Tapes contains some of the earlier versions.

See the Wikipedia entry for this album. [Amazon]

Oh Mercy (1989)

Bob Dylan album cover

With this album we jump forward fifteen years and almost out of the Eighties. It was produced by Daniel Lanois and was, according to Dylan’s Chronicles rather difficult at times to construct and record. The first song, “Political World,” really sets the tone and feel for the album and is unlike anything I had heard previously from Dylan.

You may have heard the song “Man in the Long Black Coat” on Joan Osbourne’s album Relish. For another Lanois-produced album with a similar musical atmosphere, see Emmy Lou Harris’ album Wrecking Ball. She covers an earlier Dylan song, “Every Grain of Sand,” from the Dylan Gospel-era album Shot of Love.

See the Wikipedia entry for this album. [Amazon]

Time Out of Mind (1997)

Bob Dylan album cover

Many people think of Dylan’s career as being anchored in a series of album trilogies and, if this has any basis in fact, this might be the first album in the latest trilogy. (As with all such statements, this is denied by Dylan, according to Wikipedia.) It was the second album produced by Daniel Lanois and it won the Grammy for Album of the Year. It is strong from start to finish.

Song highlights for me include “Not Dark Yet,” “Cold Irons Bound,” and “Highlands.”

If “Dirt Road Blues” doesn’t get you moving, I don’t know what will.

Dylan is back in full poetic form on this album, as in “Tryin’ To Get To Heaven”:

People on the platforms
Waiting for the trains
I can hear their hearts a-beatin’
Like pendulums swinging on chains
When you think that you lost everything
You find out you can always lose a little more
I’m just going down the road feeling bad
Trying to get to heaven before they close the door

The blues live.

See the Wikipedia entry for this album. [Amazon]

Modern Times (2006)

Bob Dylan album cover

As I write this entry, this album is the latest by Dylan and returns in full force to the quality of Time Out of Mind. Unlike that album but like the intermediate “Love and Theft”, Dylan self-produced this under the pseudonym “Jack Frost.” I can’t recall seeing one bad review of this album, and I concur.

The kickoff song, “Thunder on the Mountain,” is notable for many reasons, including his interesting rhyme for “orphanages,” which I suspect is a first. When Katie and I saw Dylan in Boston in late 2006, this was the first song in the encore.

I think the most poignant song here is “Workingman’s Blues #2”, and recalls, in my mind, some of Dylan’s early influences such as Woody Guthrie.

See the Wikipedia entry for this album. [Amazon]


  1. Wow Bob, what a fantastic list! I bought a handful of “No Direction Home” DVDs and donated them to local libraries along with one assisted living and one nursing home facility. The activity directors love it because Dylan spends so much time explaining (and detailing) his early influences. There’s so much in Martin Scorsese’s to captivate you beyond the music. The stories that Bob Dylan, the NYC folk scene, Pete, Seger, Woody Guthrie, Allen Ginsberg, Liam Clancy, Joan Baez, and many others share won’t let you hit the pause button. My only gripe is that it stops at 1966, but it’s a great start, and shows how Dylan has been a large part of American cultural history for well over fifty years.

  2. While “Love And Theft” got all the awards, in my mind “Time Out Of Mind” rules. I find myself playing it over and over.

    Instead of “Oh Mercy”, I’d go with “Slow Train Coming”. The lyrics to “I Believe In You” are haunting.

    Now you’ve done it. I’ve gotta go get my Dylan fix right now.

  3. I’m with you there re TOoM. I just find myself playing Oh, Mercy a lot these days and I thinks really kicks off everything that follows.

  4. I prefer “Bringing it all back home” to “Highway 61” which is closer to the transition, includes Bloomfield and Kooper playing organ and Dylan’s try to make “Mr Tamborine Man” his own after the Byrds changed it and his music forever.

    BTW You’ll want to grab Dylan Hears a Who which mashes Dylan and Seuss. The Dylan of BIABH.

  5. Paul, respectfully, Bloomfield and Kooper are on “Highway 61 Revisited,” not the earlier album.

    I now find it painful to listen to the Byrds’ covers of Dylan.

  6. My bad. What I get for posting just before running to class to talk about cultural remixes. Point is that the rock experimentation and some great different songs writing are in BIABH. You can heard Dylan changing here — back to rock from Folk.

    Love the Byrds and their covers. ;->

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