I Listened to All of Bob Dylan's 39 Studio Albums—You Should Listen to 12

At least 30% of Dylan's music has high artistic merit and is worth listening to over again.

Bob Dylan looms large in my mind. He’s always been there. My earliest memory of him was hearing his music in Forest Gump. He’s credited with three songs on the movie: “Blowin’ in the Wind”, “All Along The Watchtower”, and “Rainy Day Women #12 & 35”. Dylan was a cultural phenomenon in the 60s. His music was the soundtrack of the anti-Vietnam War protest culture.

He broke into the pop culture zeitgeist with his 1963 album, The Freewheelin’ Bob Dylan. Mind you, this was a year before The Beatles came to America. Dylan’s meeting with The Beatles in 1964 has become an urban legend of its own. The point is that John, Paul, George, and Ringo were starstruck upon meeting Bob Dylan. He was a big deal and a bonafide legend before age 25. 

As some of you know, I’m a big fan of listening challenges. I listened to the 2012 and 2020 lists of Rolling Stone Magazine’s 500 Greatest Albums of All Time. Dylan was constantly on those lists and I often dreaded his albums. Why? I don’t know. I just didn’t like what I heard. Maybe it's his delivery, his long-winded songs, or I just don’t “get” Dylan. Regardless, I wasn’t about to let Dylan’s music defeat me. I wanted to understand him. So why not listen to all of his studio albums in chronological order?

The System

Like my other listening challenges, I used a spreadsheet to stay organized. I created columns for the release year, album title, a checkbox, a 1-5 rating, and an album review. Each row represented an album. I also did this challenge with a few friends for fun.

For the 1-5 rating, here’s what each number represents to me:

• 1 = awful, never want to hear it again, almost no artistic value

• 2 = not great but there’s something there

• 3 = pretty good, I might listen to it again

• 4 = a great album that deserves another listen and has artistic merit

• 5 = perfect, added to regular album rotation, and highly recommended

Album Rankings

Here are my overall rankings of the 39 albums:

• 5: 3 albums

• 4: 10 albums

• 3: 15 albums

• 2: 10 albums

• 1: 2 albums

My average score for Bob Dylan’s studio albums: is 3.02. His best decades of production were the 1960s (7 albums) and 1970s (4 albums). Between 1978 and 2017, none of his albums ranked better than a 3. It wasn’t until his release of Rough and Rowdy Ways in 2020 that I felt he released a 4-ranked album. I listened to 27 albums back-to-back that were average at best.

My Favorite Albums

This list of albums represents my favorite Bob Dylan albums in order:

1. Blood on the Tracks

2. Highway 61 Revisited

3. The Freewheelin’ Bob Dylan

4. The Basement Tapes

5. Bringing It All Back Home

6. The Times They Are a-Changin’

7. Bob Dylan

8. Blonde on Blonde

9. Nashville Skyline

10. New Morning

11. Rough and Rowdy Ways

12. Desire

Beyond this list of 12, I would pass on all of his other albums. But 12 out of 39 albums are still pretty good. That means at least 30% of his work has high artistic merit and is worth listening to over again. 

If you’re kind of interested in Bob Dylan then I would highly recommend listening to Blood on the Tracks, Highway 61 Revisted, and The Freewheelin’ Bob Dylan. Those three albums are the best representation of his work from where he’s been, was, and is going. 

Blood on the Tracks

This is my favorite Dylan album. The songwriting on this album is exceptional. I think this album has more in common with Freewheelin' than any of his other albums. The songs feel autobiographical, even if Dylan denies it. Clearly, he's writing about a failing relationship between two people. This makes sense since he was separated from his then-wife Sara at the time. What I like most about this album is the sincerity of each track. Nothing feels tongue-in-cheek like some of his other songs.

Favorite track: Shelter from the Storm

Highway 61 Revisited

The first 100% electric album Dylan released is easily one of the best rock albums ever. The progression he makes in three years is staggering. Most artists will never make the transformation he has in 30 years but he does it in 3. I really think this album is as progressive as what the Beatles or the Stones were doing at the time. 1965 feels like a transitional year in rock music where artists were experimenting more and pushing their sound beyond blues and folk standards.

Favorite track: Like a Rolling Stone

The Freewheelin’ Bob Dylan

Easily the most dramatic shift any artist has taken from their first album to their second. Dylan went from playing mostly covers to writing some of the most prolific folk music ever. This album sounds like it could be Bob Dylan’s greatest hits. It is quite the transformation in such a short period of time.

Favorite track: Don't Think Twice, It's All Right

My Final Takeaway from Listening to Bob Dylan’ Albums

Love him or hate him, Bob Dylan is an original talent that deserves all of his accolades. He could have retired before 1970 and been classified as a legend. Instead, he kept writing music and releasing albums. Even when people didn’t want what he was selling, he still persevered by writing and recording the music he wanted to make. 

Not once during this project did I feel like he was phoning it in and being disingenuous. Sure, I thought Street-Legal sounded a bit like Bruce Springsteen. And his early 80s albums sound dated because of the production standards of the time. But overall he stayed true to his artistic merit and did what he wanted.

When you listen to an artist’s catalog from start to finish, you hear ideas being formed and matured over time. I think the best example of this is his stretch from 1965 to 1969. He hits the scene with folk music but then transitions into electric rock music. From there, he progresses his sounds with blues-based rock and then transforms into country western. You can hear what he’s reaching for but doesn’t quite reach it until the next album or two. 

The same thing happened with his gospel albums of the late 70s and early 80s. He dives deep into gospel singing and reggae rhythms. He then blends the gospel sound with 80s production in Down in the Groove, which I don’t think worked well at all. Regardless, he’s pushing his sound and creativity beyond what people expected out of him.

And if you’ve done anything creative then you know that changing a working formula is the hardest thing to do. Virtually no popular music artists do it better than Bob Dylan and David Bowie. I think Bowie has more popular appeal than Dylan, but critically, they’re similar. 

I thought I would have felt exhausted listening to all of Bob Dylan’s albums, instead, I’m left with a feeling of inspiration. He’s a perfect example of somebody who shows up and does the work. He never rests on his laurels and for that, he’ll go down as one of the greatest musicians of all time.

More Bob Dylan

If this post wasn’t enough and you want more Bob Dylan then don’t hesitate to check out the spreadsheet I used to listen to these albums.

I also created a playlist with my favorite songs from each Bob Dylan album. Enjoy!