Klinger: It seems like it's been forever since we checked in with our old friend Bob Dylan. Bob has an astonishing 20 albums on the Great List of the most acclaimed albums of all time, although the triptych of LPs he released in 1965 and 1966 (Bringing It All Back Home, Highway 61 Revisited, and Blonde on Blonde) established Dylan as a critical force and have always garnered the lion's share of critical acclaim. We've covered all three of them, as well as the 1975 Blood on the Tracks, and you have been, to put it charitably, a tough sell regarding the works of His Bobness, so I'm curious as to how you'll respond to The Freewheelin’ Bob Dylan, his pre-electric second album and the one that launched him into the public consciousness.
For a long time, I was pretty sure I had this album completely internalized — after all, I picked it up when I was a college kid, and songs like "Blowin' in the Wind", "A Hard Rain's a-Gonna Fall", and "Masters of War" are songs that I might think are completely ingrained in any pop fan's DNA. But this past trip through the album just keeps revealing stuff to me. Yes, Dylan's lyrical facility is obviously stunning, but you might sometimes forget the sheer breadth of his capabilities, his ability to turn on a dime from blinding anger to infectious humor to warm tenderness throughout this album. Not to mention the fact that The Freewheelin’ Bob Dylan was released a few days after the guy's 22nd birthday. Twenty-two, Mendelsohn. Think of that.
Mendelsohn: I’m not going to lie, I find that fact truly amazing. Dylan goes from being an unknown teenage singer-songwriter whose debut album sold just enough records to cover expenses to penning one of the most transformative records of the '60s. He was so young it simultaneously hurts my head to think about and makes me jealous. Although, at 22 I was pretty good at Tony Hawk’s Pro Skater 2. The thing I don’t really understand is exactly how he goes from being an untested commodity to becoming the voice of a generation. Was it organic growth? Or did he sell his soul to the Devil?
History tells us that Dylan’s growth had a lot to do with him moving in with his girlfriend in New York, Suze Rotolo, who subsequently went to Italy to study art. Her absence apparently had a profound effect on him and spurred his songwriting. He also took a trip to England and picked up some first-hand experience with traditional British folk music. The combination of Dylan’s American blues and the British folk music lies at the heart of this record, creating a firm foundation for his expanding lyrical explorations. That sounds completely plausible; however, I’m more inclined to lean toward demonic intervention. How else do you explain Bob Dylan?
Klinger: It's also possible that he was able to absorb so much from all of his surroundings because he didn't have access to Tony Hawk's Pro Skater 2. I'm not sure why we're bringing Satan into all of this, especially since he's lived long past the age of 27. Dylan began absorbing everything around him from the time he started hanging out around the University of Minnesota to his move to Greenwich Village, he was picking up everything he could get his hands on. (He also apparently had a habit of not necessarily returning the stuff he was borrowing from people, which may serve as an apt metaphor somehow.)
And yes, those influences crop up all over The Freewheelin’ Bob Dylan, but unlike his debut album, he was making all these influences and making them his own. Whether he nicked a bit here or there from whatever to make "Blowin' in the Wind", he still managed to write "Blowin' in the Freakin' Wind". And even if he hadn't managed to take his career where it was about to go, "Blowin' in the Wind" would still be with us today. But (and I hate to point this out), I can’t help noticing that you've dodged my initial question: Is The Freewheelin’ Bob Dylan the Dylan album that's finally turned your head around on Dylan?
Mendelsohn: You can sell your soul to the devil and live past the age of 27, Klinger. It just requires certain other, uh, concessions. And I think it's pretty obvious that Dylan did indeed do the deal and I don’t really want to think about what else he had to do aside from handing over his everlasting soul. Have you seen him lately? Pencil mustache, black suits, and dead, soulless eyes. Let’s just jump to the obvious conclusion.
I dodged your initial question because you didn’t really ask it in the first place and I didn’t want to blithely lead with, “I hate this record — what have I done to you to deserve this torture?”
I don’t really hate this record, but I find myself yelling at the record player from time to time and then skipping ahead to the next song, especially while I’m listening and trying to do something else. There is a droning quality to it that I can’t shake. Freewheelin’ can be so monotonous. I’m a little more forgiving of the record when I’m listening through headphones. It’s much easier to pick up the nuance, the hidden melody, and the lyrical acuity. But even then, I want more. I want electric. I want a beat. I know I’m a little ahead of myself but I can only take so much folk music, even with heavy influence blues and British traditionals, it starts to grate upon my ears like a malfunctioning refrigerator after a while. It’s not Dylan and it’s not you, Klinger. This is all on me. Ok, well, maybe it’s Dylan.
Klinger: No, it's you. Because I can't help but find it odd that you're not hearing the full range that's going on here — especially the humor. Between "Talkin' World War III Blues", "I Shall Be Free", and "Bob Dylan's Blues", this is often a very funny album. (Funny Bob is a Bob that doesn't get much ink, but there are terrific examples on nearly all of his albums throughout his career.) His offhanded delivery and palpable love for wordplay and perfect turns of phrase have kept his comic songs fresh even after 50-plus years.
And yes, "Masters of War" is based on a drone-like chord progression, but it works because it's completely in service to the song. The angst and rage that he feels comes through in every line, and it's made all the more powerful when you consider that, for 21-year-old kids like him across the country, the threat of war was just beginning to be made real, both in the Cold War terror of the Cuban Missile Crisis (I don't think people from our generations fully grasp how it meant to feel like nuclear annihilation was standing on our doorstep) and in the (at the time) more abstract worries in Southeast Asia. I don’t want to tell you how to listen to this album or anything, Mendelsohn, but I might suggest that you lean forward a little bit with this one.
Mendelsohn: I know its me. I got this thing with Bob, it’s hard to overcome. The more I lean forward, the more I want to lean back, reach over to the shelf, and grab a different record. The thing is, I understand how great this album is. It is at turns funny and wistful, a sad lament for the love of his life who is off in a far away land, and a searing indictment of the worst part of humanity. He covers all of the ideas with an ease that is unmatched for almost anyone, let alone a 22-year-old kid, and he does it with such self-assuredness that it’s hard to question his conviction. Freewheelin’ flows from point to point, turns on a dime, and then wanders off into the absurd only to bring reality crashing back down with stark witticism.
As great as the lyricism is on this record, Dylan still needed work on the music side of the equation. He’s a little rough, a little repetitive, and while that may be the nature of his folk music, it can be bland and that makes me wonder if Freewheelin’ is just a one-trick pony. Let me ask you this: if “Blowin’ in the Wind”, wasn’t on this record, would we be having this conversation?
Klinger: Well we would, because I'm going to make you talk about Dylan until you finally kill me. In fact, just to punish you further, Empire Burlesque is now on the docket. Brace yourself. But yes, "A Hard Rain's a-Gonna Fall" and "Don't Think Twice It's Alright", to name but two examples, could also have served as tipping points for Dylan's career, whether for the lyrics or, to counter your argument, the melodies. I've said this before but it bears repeating — part of what makes Bob Dylan's songs so compelling and so coverable is his gift for melody. And yes, with his not-conventionally-beautiful voice, that gift becomes all the more necessary. Also, the album was actually a hit, reaching No. 1 in the UK and a respectable No. 22 Stateside.
But I can only assume that you're just being your usual delightful contrarian self here, Mendelsohn. Because I simply cannot imagine that someone could sit and listen to an album that's this varied and yet so consistent and not be in awe. And then to think that this is only the very beginning of his rise is almost too much to contemplate. The Freewheelin’ Bob Dylan might not be Dylan's debut, but it does mark the official arrival of one of the 20th century's driving musical and cultural forces.