The Freewheelin’ Bob Dylan occupies roughly the same place in my development as a music fan that the first nervous teenage toke of a joint does in the life of a future heroin addict. Every day after grade school I’d be alone all afternoon until my parents got home from work. My companions, in reverse order of influence, were cats, television, and mom and dad’s dusty old records. Over many an afternoon, my musical teeth were cut on repeated playing of the Beatles, the Stones, the Doors, Janis Joplin, CSNY, Simon & Garfunkle, and Bob Dylan. In particular this album by Dylan. Years later, when I finally forayed into the world of CDs, this was one of the first CDs I got as well, carting it off to college with me.
One of the chief problems with having put in more than a quarter century of listening to it is that I can hardly hear it anymore. I mean really hear it, beyond all the accretions of its place in my life, and history and indeed music history in general. Having tried to do that just now, I observe mostly how young an album it is. It’s the first one where Dylan is Dylan- in exact reverse of his debut Bob Dylan, it’s almost all originals, with only two covers. He’s stretching out and finding his voice here, and as a result his voice is all over the place- both literally and lyrically.
In traveling from the rough-hewn and timeless “Blowin in the Wind”, to the out and out absurd horsing around of “I Shall Be Free”, the overall sense I get is of a powerful car being taken for a test drive by a kid who doesn’t quite know how to drive it yet. So, for example, on “Don’t Think Twice, It’s All Right” we find him in the emotional territory of the bitterness of failed relationship that he’ll mine extensively later, but he plays it too consciously jokey to really turn the knife. Or hear him having fun with the mythology of the Western plains on “Bob Dylan’s Blues” (Well, the Lone Ranger and Tonto/ They are ridin' down the line/ Fixin' ev'rybody's troubles/ Ev'rybody's 'cept mine/ Somebody musta tol' 'em/ That I was doin' fine) but not yet able to tap its genuine power as he later will with the Band.
On the tight corners that really matter though, he pulls out the bitter, poetic and razor-sharp focused “Masters of War”, the surging symbolic “A Hard Rain’s A-Gonna Fall” and the Swiftian satire of “Talking World War III Blues”. If he’d never recorded anything beyond these three songs, he’d already have surpassed the lifetime achievement of many another songwriter.