1. “Desolation Row” (1965). Simultaneously hilarious and sad in that off-the-cuff surrealistic way that came so easily to Dylan once he realized he was younger than that now. And unlike the slightly longer “Sad-Eyed Lady of the Lowlands” he’d record one year later, this song’s images--thanks in no small part to Charlie McCoy’s acoustic-guitar filigrees--flow as naturally together as a river to the sea, and wherever those rivers go, you want to be. As with “Ballad of a Thin Man,” drugs might accelerate one’s access to exactly what, or at least where, Dylan thinks Desolation Row is, but they’re not necessary because the song itself is drugs enough. Besides, the best lines make more sense when received out from under the influence: “Everybody is making love / Or else expecting rain” is a pretty accurate description of the human condition. Eventually you discover that Dylan, by loading representatives of practically every category of mankind (real and imagined) into his ark, is telling us that Desolation Row is everything or at least everywhere--a perpetual dark-night-of-the-soul 3 A.M. And unlike “Sad-Eyed Lady of the Lowlands” (and the dark night of the soul), when “Desolation Row” is over, you wish it weren’t.
2. “Don’t Think Twice, It’s All Right” (1963). The twenty-two-year-old Dylan delivers this restless farewell so succinctly that he sounds almost happy to be leaving his woman-child lover or at least convinced that she’s to blame. But a bounder who was really happy to be saying goodbye would write something along the lines of “This woman’s so crazy, I swear I ain't gonna touch another one for years,” not “Still I wish there was somethin’ you would do or say / To try and make me change my mind and stay.” And no cad who genuinely believed it was the woman-child’s fault would spend so much time trying to convince himself of it, especially with transparently insufficient arguments. “I give her my heart,” he sings, “but she wanted my soul.” Surely, Dylan must have known that when you fall in love, you fall in love heart and soul, the way a fool would do gladly. What he probably really didn’t want to give her was his money. As the oft-married (and oft-divorced) Harlan Howard once said, “The next time I feel like getting married, I’m just gonna find me a woman I don’t like and buy her a house.”
3. “Dignity” (1989). Interesting trait to write a song about. Most songwriters stick to variations on faith, hope, love, and getting’ rich or dyin’ tryin’. Not Dylan, though, for whom dignity clearly has nothing in common with either pride (cf. “Foot of Pride”) or grace (cf. "Saving Grace") and certainly not conceit (“Disease of Conceit”). Those you can find everywhere. Dignity, on the other hand, can’t be found anywhere--not in a cotton field, not at a murder scene, not in the pockets of chance, not at Mary Lou’s wedding, not in all F. Scott Fitzgerald’s books, and certainly not in yourself (or you’d never go searching high and low for it in the first place). So there’s really no need to hurry. Which is probably why the song, paced by Willie Green’s loping drums, doesn’t.
4. “Dear Landlord” (1968). Landlords--you can’t live with ’em and you can’t live without ’em. They punch your cigarette, strap you to a tree without roots, intrude when you’re in the darkness, and utter idle words with a reprobate mind. And that’s just what’s good about them. Judging from the defeated tone in his yearningly mournful vocal, Dylan seems to know as much. Or as he would later write, “Sometimes I think this whole world / Is one big prison yard / Some of us are prisoners / The rest of us are guards.” And later yet: Why our “hearts must have the courage for the changing” of the latter.
5. “Dirt Road Blues” (1997). One of the few songs on Time Out of Mind that you don’t have to be recovering from a hellish breakup to feel in your bones. It helps, of course, to have looked for the sunny side of love after rolling through the rain and hail and to have run away and hidden after not having found your “baby,” but no more so than to have prayed for salvation in a one-room country shack, put up barriers to keep yourself away from everyone, or sung in your chains like the sea. Anyway, what helps the most is the junkyard racket that Daniel Lanois got from his band of merry noisemakers and the way he made it echo like a hell storm.
(Top-Five Bob Dylan Songs Beginning with "C": http://arsenioorteza.blogspot.com/2010/07/bob-dylans-top-five-songs-beginning_30.html)