Bob Dylan – The Freewheelin’ Bob Dylan: #852 of best 1,000 albums ever!

Bob Dylan - The Freewheelin Bob Dylan

Why is Bob Dylan’s The Freewheelin’ Bob Dylan on my best 1,000 albums ever list?

Take a freewheelin’ classic folk rock ride with a young artist named Bob Dylan, early ‘60s style.

What does Bob Dylan’s The Freewheelin’ Bob Dylan mean to me? What does it make me feel? Why is it exciting or compelling?

The Freewheelin’ Bob Dylan, from its iconic album cover (see more on that below) to the simple fact that this is an early ‘60s back-in-the-day Bob Dylan record, makes it feel like Rock n’ Roll Canon or some such. Something so iconic and revered that to even attempt to catalog it, the audacity to rank it even on some kind of fangled best 1,000 albums ever project (at that!) is to surely be a foolhardy undertaking.

And perhaps it is. But I’ll preamble (pre-ramble ramble, perhaps?) further in stating that I’m a huge Bob Dylan fan. But what’s so great about being a Bob Dylan fan – and so great about Bob Dylan as artist itself – is that his catalog is so mind-bendingly huge, spanning such a vast amount of time (and American history!) and such a huge amount of creative output (most of which is somewhere between pretty great and all-time classic), is that, I realized, it’s okay to dig some stuff more than others.

And, further! I’ll add that this is one of those times when I can lean ever so slightly on where the Rolling Stone greatest 500 albums ranks this one (#255) and how I’m ranking it (#852) out of 1,000 simply in terms of thinking, okay, I’m placing it about 600 slots lower with my own highly eclectic and personalized project but feel pretty good about having this particular one right here in terms of the overall rankings.

Which is all to say: The Freewheelin’ Bob Dylan is the “lowest” ranked Bob Dylan record that I’m including on the best 1,000 albums ever, but there will be more albums to come.

See how fun this freewheelin’ ride is?

I’m writing these words about a week after Russia’s shocking and appalling invasion of Ukraine, so therefore must start with “Masters of War,” a haunting and beautiful folk song that seems incredibly relevant right now. Like most great art, it can be interpreted in many different ways, and it’s hard not to think about the evil of one man, Vladimir Putin, when hearing Dylan’s voice emitting words written some six decades ago:

You that never done nothin’
But build to destroy
You play with my world
Like it’s your little toy

Among other things, Dylan was at the forefront of folk and rock artists who expressed the feelings and frustrations of the younger generation of the era, which would soon be known as the “counterculture.” What’s interesting is that “Masters of War” was released in May 1963, a time of relative of relative peace and prosperity in the United States. It was before the U.S. had gotten mired in the Vietnam War, and was some six months before President John F. Kennedy got assassinated, a pivotal moment that felt to many like a loss of innocence.

Thinking about the year 1963, I’m reminded that Americans tend to forget again and again over our history that just because we get lulled into thinking global events can’t affect us, they can. And they will.

And on that note, don’t get me started on the song title, “Talkin’ World War III Blues” on this album.

Let’s move onto “I Shall Be Free,” a deep cut that I enjoy immensely. It’s got such a loose, flowing feel, with outstanding harmonica work and the production makes you feel that Dylan is sitting on a chair performing for you in the same room. Just gorgeous.

“Blowin’ in the Wind” is obviously one of those Dylan Mount Rushmore songs, but it’s not one of my favorites. Again, that’s the beauty of Dylan. And, okay, I’m listening to it while I write these words and it’s pretty damned good, okay?

It feels like you could insert “Don’t Think Twice, It’s All Right” into a certain scene in almost any dramatic film or TV series and it would totally work, doesn’t it?

Pop culture stuff that’s somehow related to Bob Dylan’s The Freewheelin’ Bob Dylan

The Freewheelin’ Bob Dylan album cover immediately reminds me, of all things, the 2001 science fiction mind bend-y thriller, Vanilla Sky, starring Tom Cruise, Penelope Cruz, Cameron Diaz, and Jason Lee and directed by Cameron Crowe.

Quick aside to say that Vanilla Sky is a vastly underrated movie. It’s phenomenally good, one of those head trip movies that is executed perfectly and is both entertaining as hell while making you think about various themes layered into the film over time.

The album cover plays a small but really interesting role in the movie that I won’t explain here as I won’t spoil it for you if you haven’t seen it. And, also, it would take up quite a few words to explain and I’m already at over 1,000 words here.

On a list of 1,000 albums where I’m writing a full blown entry/review for each. That’s a lot of words, people!

Some stats & info about Bob Dylan – The Freewheelin’ Bob Dylan

  • What kind of musical stylings does this album represent? Rock Music, Folk Rock, Pop Music, Album Rock
  • Rolling Stone’s greatest 500 albums ranking – #255
  • All Music’s rating5 out of 5 stars
  • When was The Freewheelin’ Bob Dylan released? 1963
  • My ranking, the one you’re reading right now – #852 out of 1,000

Bob Dylan’s The Freewheelin’ Bob Dylan on Spotify

What does the “best 1,000 albums ever” mean and why are you doing this?

Yeah, I know it’s audacious, a little crazy (okay, maybe a lot cray cray), bordering on criminal nerdery.

But here’s what it’s NOT: a definitive list of the Greatest Albums of All-Time. This is 100% my own personal super biased, incredibly subjective take on what my top 1,000 albums are, ranked in painstaking order over the course of doing research for nearly a year, Rob from High Fidelity style. Find out more about why I embarked on a best 1,000 albums ever project.