Admittedly the title of this post is a bit ironic. I've listened to Bob Dylan since I picked up The Freewheelin' Bob Dylan at least 25 years ago, and quickly found my favorite albums of his: Highway 61 Revisited, Blonde on Blonde and Blood on the Tracks and Desire. But whenever I hear someone talk about Dylan I realize I only know a condensed selection of his catalogue. That's just fine, really, but wouldn't it be nice to maybe find some new favorites among his albums now that we both are older?
I decided to give listening to his back catalogue of studio albums a try. I will begin from the beginning, skip any bootlegs, live albums, collections of hits, covers or B-sides. Apart from the most significant ones, that is. I think that about 40 records count towards his main catalog, and that's enough.
I'll write my thoughts below and try to learn a bit about the album, read some lyrics, and maybe understand the context. Then they deserve a review and possibly a re-listen of course.
I thought of listening in reverse chronological order just to get a build up to greatness and history. I already know the last 15 or so of his records will be a bit of a hassle for me to listen through, although I also know they have some real gems sprinkled among rudimentary traditional blues jams and vague ballads with little melody. In the end, how do you really get to know someone by seeing their progression backwards? I want to figure out how he evolved, and that would be really weird in reverse order.
First up is Bob Dylan's debut album, by a kid chasing his heroes, with his whole life still ahead of him.
- Bob Dylan (1962)
- The Freewheelin’ Bob Dylan (1963)
2025-09-24
This is the album that shifted an entire scene, and in part shifted the entire culture. Not many albums have a distinct before-and-after watershed moment, but this one has. It was released as criticism of the growing Vietnam War was growing and it definitely sparked belief that counter culture could have a say in the future of the US attempts to place a chokehold on the political evolution abroad.
He recorded The Freewheelin' Bob Dylan at 21 years old. This time he wrote all songs himself. It was my first Dylan record and I first listened to it at 17.
Freedom and human morality anthems such as the beautiful and iconic Blowin' in the Wind and the grueling anti-war song Masters of War which takes a stab at profiteers of war, stand in contrast to the softer but also sadder love songs like Girl From The North Country, Don't Think Twice It's All Right, although the latter has a bitter bite to it. He resigned from the relationship, but he didn't resign from getting the last word in.
It's hard to name songs on this album without praising one of the most powerful ballads of all time. A Hard Rain's a-Gonna Fall which feels like Jesus himself is retelling his experiences in the final days. The song may sound hopeful at the end but hope is not the word that comes to my mind when each line of this song falls hard on all my senses as Dylan softly states his words with a neutral matter-of-fact delivery. This song deserves another listen even if you know it by heart.
2025-09-20
This album was recorded on a minimal budget when Dylan was just 20 years old. John Hammond of Columbia Records discovered him in the West Village clubs and seemingly lifted him right into the studio. The album art shows a kid with confidence but not much experience, but the songs show something else. Dylan takes on roles of singers who came before him and who inspired him to go seek his fortune in New York. I assume many of these songs are what he heard on the scene rather than what he heard on the radio back home.
I read somewhere that this is where Dylan was still testing various styles to see what fit him and what resonated with the audience. Apparently he thought the album was a bit simple, rudimentary and unoriginal, but obviously other people in the West Village post-beatnik folk scene saw it as raw, unusual and personal.
The album has only two original Bob songs and the rest of them are covers or traditional folk and blues songs. It struck me how this tradition of playing other people's songs as if they were your own really lives on today whether he is playing live or playing songs on the Theme Time Radio Hour that he broadcast for a few years in his fairly recent years.
The first song opens up with him singing to his frantic guitar sounding like a Jewish Elvis, almost as if he's trying to summon his inner Jerry Lee Lewis, who he is not.
Talkin' New York follows and it's an amazing song. He is emulating Woody Guthrie and I hear how Johnny Cash did the same later on. We can really see his humor shining through here but it's dry, experienced sounding and a bit distant. He incorporates themes of protest songs, class and the worker's perspective.
In My Time of Dyin' is religiously bitter, and Gospel Plow strikes me as a religious possibly black working song. Baby, Let Me Follow You Down is another amazing song that could well be played in church.
He has some aggressive tracks as well. Fixin' to Die is bitingly angry and in Highway 51 Blues he sings as if he was Mick Jagger, almost.
Pretty Peggy-O and Freight Train Blues are playful tracks which give another dimension to the otherwise often grumpy Dylan. He had some fun with these ones.
The best tracks on the album are the sad beautiful ballads that carry the themes of love, regret and sadness. These tracks are Man of Constant Sorrow (this track must really have presented him as a miracle kid to the scene) (and this reappeared in the film O Brother Where Art Thou almost 40 years later), the stolen but beautiful female perspective House of the Risin' Sun, Song to Woody and See That My Grave Is Kept Clean.
The first album didn't sell well and Dylan didn't become a world wide phenomenon for another year when his second album broke.
I can definitly see myself revisiting this album in the future. It's classy without being too played out in a way, like The Freewheelin'. It sounds nice and raw at the same time and is a real history marker.