It's funny you should mention Dylan.
Since you left town, I have of late (and wherefore I know damn well) entered full obsession mode--buying bootlegs and records I know will be shitty just to hear them for myself, then finding ways to defend them (you know the drilly)--and that demands an overarching thesis, preferably untenable, suitable for arguing well into the night. My latest attempt addresses the problem people seem to have with getting into him, his voice, his world, his paradigm--of even knowing where to start. It has less to do with his daunting body of work than with the fact (say I) that Dylan's songs, more than being about any specific subject--love, loss, justice, Jesus, Woody Guthrie, Willie McTell--are about the experience of being a given age.
In the early '60s, when Dylan was in his early 20s, the world was divided into The Young and Everyone Else. As a result, he became the poet laureate of those under 30, addressing their concerns and finding simple, elemental metaphors (the wind, the rain) to communicate them to the world. As the generation--and yes, I know how awful a word that is, and yes, I demand that you acknowledge that it's uniquely appropriate for this discussion (or is it a diatribe?)--evolved from being led by pangs of conscience to hearing the call of full-blown hedonism (Slouching Towards Bethlehem, anyone?), Dylan evolved from pious, acoustic folk-revival poster boy to drug-addled, electrified surrealist poet rock star. Having realized how far beyond everyone he truly was (what 22-year-old hasn't felt that?), he invented a whole new iconography. This progression can be caught between 1961 and 1966, on the LPs Bob Dylan, The Times They Are A-Changin', The Freewheelin' Bob Dylan, Another Side of Bob Dylan, Bringin' It All Back Home, Highway 61 Revisited, and Blonde on Blonde.
Then, all of a sudden, motorcycle crash or no motorcycle crash, there he stood, in his late 20s, overcommitted, underunderstood, rich, famous, lost. He turned inward, and started making a new kind of folk music--wandering, ponderous, beautiful. He experimented with classicism, much the same way a 29-year-old man flirts with classic forms of manhood--marriage, say, or career, or moving away--as he finds himself pushing 30 and still worried about his teenage heartbreak. (For more on this period, see John Wesley Harding, Nashville Skyline, The Basement Tapes (!!!!!), and New Morning.)
Next come his 30s (and ours), and with them divorce, regret, despair, resignation, rage, the failure of his attempts to settle down, the reemergence of old demons with new faces and redoubled powers, and the final realization that all bondage is self-imposed and that you can't pretend to be what you're not. This is Planet Waves, Blood on the Tracks, Desire, two live albums (one a double LP), a feature film, and the greatest tour concept of his career (the Rolling Thunder Revue). This is a man baring his roiling soul for the first time, howling from the depths of pain that has been there from the start, lashing out in search of a culprit and finding... who else? The crucial couplet, from "Idiot Wind": "I've been double crossed for the very last time and now I'm finally free/I kissed goodbye the howling beast on the borderline that separated you from me." (I don't know about you, but I'm beginning to recognize the shape of that beast and the location of that borderline.)
And then onward, into his late 30s and early 40s, the years when a man can get lost. I think of this period as meandering--it's Christian boogie R&B, delusion and conviction and complacency, leather vests with no shirt underneath. Some amazing songs ("You Gotta Serve Somebody," "Every Grain of Sand," "Groom's Still Waiting at the Altar"), but some terrible ones, too. As I lose sight of him in the middle distance of middle age, I wonder if it's because he thinks he knows the answers and he's wrong, or because there aren't any answers to get. Then again, I'm not 40 yet, am I?
Am I? (Don't answer.)
PS: This theory falls to pieces when you consider how amazing he has been between ages 50 and 60 (Good As I Been to You, World Gone Wrong, Time Out of Mind, and especially Love and Theft)--unless of course you write it off to a grandfather clause....