1. “Black Diamond Bay” (1975). A masterly shaggy-dog tale wagged by Howie Wyeth’s shaggy-dog drumming. Dylan once said he wanted to make a movie out of “Tight Connection to My Heart” because, of all the songs he’d written, it “might be the most visual…. the one that’s got characters that can be identified with.” He then added: “Whatever the fuck that means.” As well he might--because he was wrong. “Black Diamond Bay,” not “Tight Connection,” is his most visual and the one that’s got characters that can most be identified with (even though, for all I know, Jacques Levy may have written the entire thing). By sympathetic characters, I don’t mean the Panama-hat-wearing lady or the fez-wearing desk clerk or the noose-wearing Greek. Nor do I mean the tiny man (maybe if I were Mike Tyson) or the soldier (maybe if I were Evander Holyfield) or the loser or the dealer. No, I mean the beer-sodden couch zombie in the last verse, too lethargic for all but the most reflexive and enervated schadenfreude, zoning out to news of the erupting volcano as transmitted from the TV screen by Walker Cronkite. “I never did plan to go anyway,” he shrugs the lug. "So it's no big deal that everything and everyone mentioned in the song was destroyed." Coincidentally, I never did plan to do Lindsey Lohan anyway, so it's no big deal that she's a drug-addled jailbird. See how timeless Dylan can be?
2. “Ballad of a Thin Man” (1965). This similarly visual song has characters that can be identified with too--especially if you’ve ever taken the drugs that Dylan was taking at the time that he wrote and sang it. For what other reason is the central character’s last name “Jones”? It doesn’t end-rhyme with any other word and therefore could’ve just as easily been “Tork” (not “Dolenz” or “Nesmith” though--too many syllables). Dave Marsh says that Dylan “lifted” the song’s melody from Ray Charles’ 1959 hit “I Believe to My Soul,” and maybe he did. And maybe Charles released “Let’s Go Get Stoned” in the summer of 1966 because Dylan’s “Rainy Day Women #12 & 35” had been a hit in the spring of 1966. And maybe you don’t have to be Ray Charles to know what it means to “put your eyes in your pocket.” And maybe you don’t have to get stoned to find yourself crying, “Oh my God / Am I here all alone?” And certainly “You should be made / To wear earphones” is the best reason to avoid being caught either grateful or dead using an iPod™.
3. “Bob Dylan’s 115th Dream” (1965). A magical history tour. Columbus, the pilgrims, Moby Dick mongrelized with Ray Stevens, Jesus, Captain Kidd, and the swindling of the Indians comprise much but by no means all of the syllabus. Going for five days without eating, getting kicked by a foot coming through a pay-phone receiver, flipping coins like Rosencrantz and Guildenstern, falling for a mercenary French girl, leaping a hot-dog stand in a single bound, and pulling down your pants for collateral comprise much but by no means all of the final exam. Just two years earlier, Dylan had written his first “Bob Dylan’s Dream,” which, for all its poignancy, was really just a sentimental re-write of a relatively unsentimental olde ballad. (If any of you feel like giving away ten thousand dollars at the drop of a hat, just tell me where it hurts ya, honey, and I’ll tell you who to call.) Dylan had obviously come a long way in a short time, and I‘d love to trace how he did. So I hereby petition Sony to add Bob Dylan’s 2nd-114th Dreams to its Bootleg Series docket.
4. “Blind Willie McTell” (1983). A tragical history tour. Of the American deep South. Of the American deep South as a wide-awake version of the world Dylan discovered while dreaming for the 115th time. Where the clogging of one’s sinuses with the centuries’-old effluvium of “power and greed and corruptible seed” is offset only slightly (but maybe just enough) by the medicating effects of “bootlegged whiskey” and the endorphins unleashed by “charcoal gypsy maidens” who “strut their feathers well.” Dylan makes it sound like one of those places that it would be great to visit but terrible to live in. But we do live in it. Which is why McTell has his eyes in his pocket. And why he sings the blues.
5. “Buckets of Rain” (1974). Five six-line verses, the longest only thirty Twitter-friendly words long, and each one a grain of sand in which you can see if not the world then at least a life. Doing not what you want to or can but what you must, evanescent “pretty people” and friends, little red wagons and little red bikes (no doubt beside white chickens and glazed with rain), a lover’s every charm causing nothing but misery--if it’s not your life yet, it will be soon enough.
(Bob Dylan's Top-Five Songs Beginning with "A":