Rainy Day Women #12 & 35 (from Blonde on Blonde) I was about 10 years old the first time I heard this song, and it’s stuck with me ever since. It was the weirdest damn thing I had ever heard up to that point.
Ballad of a Thin Man (from Highway 61 Revisited) An absolutely scathing blues number, this is my favorite cut from Highway 61 Revisited. Dylan’s piano and Al Kooper’s organ complement each other perfectly to evoke a slight feeling of dread.
One of Us Must Know (Sooner or Later) (from Blonde on Blonde) Well I guess you couldn’t accuse Dylan of being a sap. Looking down on the wreckage of a ruined relationship, this song is unapologetic in every way.
All Along the Watchtower (from John Wesley Harding) It’s practically a haiku, by Dylan standards; 135 words that evoke an entire world, a tiny corner of a big picture — miniature in scale, epic in scope, a mystery with no bottom.
Political World (from Oh Mercy) The first Dylan record in forever to seduce you with the way it sounds. The simple, obvious thing that producer Daniel Lanois does here is to structure the arrangement as an ever-evolving series of crescendos as the song verses pile up, rising from a solitary murmur to a raging full-band firestorm.
All I Really Want To Do (from Another Side of Bob Dylan) The exception in a catalog that has never been noted for its generosity of spirit. With sheer sunny brio, Dylan does the impossible; he makes openheartedness sound cool.
A Hard Rain’s a-Gonna Fall (from The Freewheelin’ Bob Dylan) The Anglo-Irish murder ballads on which Dylan modeled the song do not editorialize; they lay out their horrors with a cool detachment. Just so, Dylan declaims his phantasmagoria with neither pity nor scorn, and the effect is mesmerizing — and terrifying.
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The Mighty Quinn (Quinn the Eskimo) (from Biograph) Songs like this make me wonder if Bobby Dylan might have been born at the wrong time — if he was forced by circumstance into the role of (as he puts it) “a song and dance man,” when in an earlier day he might have been a song-pitcher.
Subterranean Homesick Blues (from Bringing It All Back Home) End-to-end packed with aphorisms, catchphrases, and more characters than your typical Broadway play. And its famous promo film cleverly literalizes the songwriter’s method; the illusion of life’s hurlyburly, spun out in real time by one man, alone in a strange place with paper and ink.
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Gotta Serve Somebody (from Slow Train Coming) Dylan’s first “born again” record wasn’t quite the departure it may seem. In poaching Dire Straits for a backing band and keeping the emphasis on swampy grooves, it’s consistently listenable — and leavened with nicely self-deprecating humor; you may call him Ray, indeed.
House of the Risin’ Sun (from Bob Dylan) Dylan’s performance of this venerable auld whorehorse on his debut finds him frustrated with the limitations of the folk medium, and with his own limitations within that medium, forecasting that his own songwriting would — must — inevitably come to the fore.
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Cold Irons Bound (download) (from Time Out Of Mind) The sound of a cache of scratchy blues 78s found in a time capsule and reinterpreted by an ensemble of Andromedans some time after the Sun goes cold — brought to you without the billion-year wait.
Positively 4th Street (1965 non-album single) The greatest fuck-you song in rock ‘n’ roll history, and by implicating himself — by refusing to let himself off the hook for his own darker thoughts — Dylan elevates it from self-righteous to righteous, full-stop.
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