1. “Like a Rolling Stone” (1966). Although I’ve always assumed that the “everybody” who must get stoned included me, there's no way I'm risking death by stoning for something really stupid--like not placing this song at the top of this list. Neither am I going to join the rogues gallery of critics who would block it up, lock it up, analyze, and categorize it. All I really want to do is say that if you have to ask why it’s the greatest rock-and-roll song ever, I can't tell you. I will, however, number myself among those who insist that having nothing to lose because you ain’t got nothing is hardly one of life’s Seven Curses. And being invisible ain’t so bad either.
2. “Lily, Rosemary and the Jack of Hearts” (1975). It takes some work, but if you rip Masked and Anonymous into a format compatible with Windows Moviemaker or its Mac equivalent, you can chop up and arrange the scenes to make a video surprisingly compatible with this song. Penélope Cruz can be Lily, Jessica Lange can be Rosemary, John Goodman can be Big Jim, Luke Wilson can be the hangin’ judge, Jeff Bridges can be the backstage manager, and, of course, Bob Dylan can be the Jack of Hearts. (Why not? His character’s name in Masked and Anonymous is “Jack Fate.”) And after you’ve spent the better part of a day or two editing the video together and then upload it to YouTube only to have the YouTube police take it down and mark your account for cancellation, you’ll know better than ever that failure’s no success at all.
3. “Love Minus Zero/No Limit” (1965). You can cynically deconstruct the lyrics of this song then reconstruct them as little more than the smart man’s “Just the Way You Are”--i.e., ostensible praise that upon examination turns out to be a veiled threat: “What I like about you is that you don’t talk very much, so if you want me to keep liking you, you’d better not be so fast that you cannot see that I must have solitude. Oh, and I also like that you can’t be bought with Valentines--saves me money on cards, roses, and boxes of candy. Best of all, you don’t argue with me or judge me. Speaking of which, I have to work late again tonight at the office….” The extent to which Dylan sells his slick talk derives from his sounding too naïve to know he’s being insincere and by camouflaging his insincerity in unforgettably vivid images that actually have nothing to do with what he’s saying: people drawing conclusions on walls, dangling cloaks and daggers, resentful chess pieces, spoiled rich girls for whom nothing less than gold, frankincense, and myrrh will do--all set to a melody so lovely that you really can’t blame a raven with a broken wing for choosing the window through which the music is floating as a good place to recuperate.
4. “Lay Lady Lay” (1969). What over-obsessive editor at bobdylan.com added commas to this song’s title (http://www.bobdylan.com/#/songs/lay-lady-lay)? I mean, for someone who can’t even spell Charley Patton’s first name, that takes a lot of nerve (http://www.bobdylan.com/#/songs/high-water-charlie-patton). And if we really must fix Dylan’s punctuation errors, why not fix his grammatical ones too and change this song’s lyrics to “Lie, lady, lie”? I’d heard “Lay Lady Lay” on the radio for years without ever knowing whose it was when in 1980 or thereabouts a friend of mine told me it was Dylan’s. (I’d been “into” Dylan for several years by then, but I’d yet to listen to Nashville Skyline or Greatest Hits Volume 2.) I didn’t believe my friend at first, but I hoped he was right because then I’d have yet another song to add to my songs-I-really-like-by-Dylan list. Pete Drake’s steel guitar drenches the descending chord changes of this invitation to foreplay-with-benefits the way Matthew Fisher’s organ drenches Procol Harum’s invitation to get stoned at a party where Bach’s on the jukebox, “A Whiter Shade of Pale.” But it’s the pillow-talk tenor of Dylan’s sublimated vocal urgency that really makes this song glow like a candle on the bedside of an irresistibly sad-eyed lady. (The fed-into-a-sausage-maker version captured on Hard Rain tastes pretty good too. A friend of mine says it was Dylan’s way of responding to having audiences shout, "Play 'Lay Lady Lay'!" one too many times.)
5. “Leopard-Skin Pill-Box Hat” (1966). Pillbox hats, leopard-skin or otherwise, aren’t in fashion nowadays, so it can be hard to imagine why the subject of this electrified barbed-wire blues inspires prickly heat in the singer, her doctor, and those who like canoodling in garages. But a Google-image search of “pillbox hat” brings up pictures of Jackie Kennedy in a pink one, and everyone knows she was only the hottest First Lady of all time. When Dylan wrote this song, the widowed former Jacqueline Lee Bouvier was still two years away from marrying Aristotle Onassis and was therefore available for the fantasizing. Who knows? Maybe it was Onassis envy that inspired Dylan to make the man who hanged himself in “Black Diamond Bay” a Greek.
(Bob Dylan's Top-Five Songs Beginning with "K": http://arsenioorteza.blogspot.com/2010/08/bob-dylans-top-five-songs-beginning_07.html)