From the beginning (well, near the beginning -- it's strange to think that songs like "Blowin' in the Wind" and "A Hard Rain's A-Gonna Fall" are essentially Dylan's juvenilia) he had an unfair advantage over other poets as a rock 'n' roller; not only did he have the poet's traditional advantage -- relief from the burden of explanations -- he also didn't have to sound serious, either. Part of the joy of Dylan is the extent to which he just seems to wing it in the time-honored, whimsical tradition of close-enough-for-rock-'n'-roll. (You might say Little Richard got there first, and Dylan might agree with you.) I think this looseness is where a lot of his lyrics come from -- like this, my very favorite Dylan couplet ever, from "Million Dollar Bash":
I looked at my watch, I looked at my wristThat is so stupid it's sublime. And that's just my particular favorite -- bear in mind, millions of allegedly half-literate teens were in 1965 singing aloud, "You're invisible now, you got no secrets to conceal," probably as in love with keening sound of CEE-ullllllllll as with the words. Some of them were even singing, "But the second mother was with the seventh son." Mind, that was the same summer as I Got You, Babe and I'm Henry VIII, I Am.
I punched myself in my face with my fist
But Dylan wasn't just fooling around. If you take the time to think about that line about being invisible with no secrets, it turns out the metaphor is even more vivid and effective. (I'm still not sure about that seventh son, though.) I'm convinced Dylan saw from early on that hipster obscurantism was not only fun and profitable but also something with which he could go hunting for the Real Thing. Some go after it thundering and blundering, but Dylan chose to sneak up, casual-like, looking like he didn't care till it was time to throw the knife. Just because you didn't want to seem serious didn't mean you couldn't be serious.
Maybe he read and took the point of Ellen Willis' 1967 critique of his "silly metaphors, embarrassing cliches, muddled thought; at times he seems to believe one good image deserves five others," etc. Maybe he figured that out himself. Maybe the motorcycle crash had something to do with it, or the bad scene after Woodstock, but his imagery and inventiveness became muted, prematurely autumnal. It took me years to figure out that he wasn't just filling measures on "The Ballad of Frankie Lee and Judas Priest"; I didn't get why Judas was laying out tens for Frankie to pick from, and why Frankie was unable to choose -- they're all ten dollar bills! -- until I started to have dreams like that too, and to think more seriously about death. Dylan was 26 when he wrote it.
Over time Dylan has come to seem much less weird, partly because we've gotten used to him and because he's been festooned with honors and become a Cultural Figure, but also because the more mastery he got over his songwriting, the more it came to resemble the work of the other masters in his field -- good American Songbook stuff, love songs and stories. (He sees that too, hence Shadows in the Night.)
But he didn't shave himself to fit that mold. Rather he pushed it out, gently, to suit himself. I remember how shocked and thrilled I was by "either I'm too sensitive or else I'm gettin' soft" -- holy shit, it's quarter to three and there's no one in the place except Bob Dylan! If his love songs didn't have the economy of a Jimmy Van Heusen song, that was okay; one of the benefits top being of the New Breed was that you were expected to be undisciplined, a little shaggy and bloated like a fat couch at a hippie house. ("If You See Her, Say Hello" = 234 words. "All the Way" = 130.)
Dylan took advantage of his allowance; some of his songs feel like director's cuts avant la lettre. "Idiot Wind" (639 words!) is like a scenario for a Sam Peckinpah movie no one could possibly finance. But along the way he learned to be sparing when needed, too, as in "Make You Feel My Love," one of the Dylan songs closest to the old tradition. The song is a plea; the lines are spare with short words, to carry the plaintive feel; the emotions are raw to the point of embarrassment. And it sneaks up on you like Dylan sneaking on the muse. See how it goes from something almost mundane to something majestic in just the first two verses:
When the rain is blowing in your face
And the whole world is on your case
I could offer you a warm embrace
To make you feel my love
When the evening shadows and the stars appearI'm not sure if this is what the Swedes meant by "for having created new poetic expressions within the great American song tradition," but it does the trick for me.
And there is no one there to dry your tears
I could hold you for a million years
To make you feel my love