"You're No Good" (Bob Dylan, 1962)
From his oft-overlooked folkie debut, a prophetic blast of rockabilly. Even in this early stage, hustling to make his name in the folk scene, Dylan's got rock & roll in his bones.
"Going, Going, Gone" (Planet Waves, 1974)
One of his last great studio performances with the Band — and also one of his catchiest songs about death.
"Black Diamond Bay" (Desire, 1976)
A tale of forbidden love, violence, treachery — plus a final-verse twist where it turns out Dylan's at home watching the news on TV, drinking a beer. Ah, the Seventies.
"Where Are You Tonight? (Journey Through Dark Heat)" (Street Legal, 1978)
A few beers later, here he is at the end of Street Legal, with his final words before collapsing into the Christian years and his Eighties malaise. He asks the same question he used to ask Sweet Marie, but this is definitely the sound of a man on the brink of a cosmic breakdown.
"Pressing On" (Saved, 1980)
Dylan's Christian period had some of his most out-there gaffes, but also this soulful (though definitely still out-there) gospel hymn about original sin. With a tinge of déjà vu, he tells the heathens in his flock, "Don't look back."
"I and I" (Infidels, 1983)
"Been so long since a strange woman slept in my bed," he sings in the opening line. Guess that's it for the whole higher-calling-of-my-Lord thing then? The slick reggae groove, cartoonishly huge drums and all, makes the case for Mark Knopfler as one of his most simpatico producers.
"Sweetheart Like You" (Infidels, 1983)
The best of his grizzled mid-life booty-call ballads. This song basically became the template for the last quarter-century of Leonard Cohen's career, for which we should all be grateful.
"Dark Eyes" (Empire Burlesque, 1985)
While Dylan was lost in synth-drums and leisure suits, not to mention line-dance videos, he went back to the acoustic guitar for this nebulous folk dirge. Judging by the lyrics, he'd been secretly listening to a lot of U2.
"The Groom's Still Waiting At The Altar" (Biograph, 1985)
The scariest of all Dylan apocalypse songs. "Cities on fire, phones out of order, they're killing nuns and soldiers, there's fighting on the border," and to make it all worse, Dylan can't get a date.
"Tight Connection to My Heart (Has Anybody Seen My Love)" (Empire Burlesque, 1985)
Deep in the wilderness years of the Eighties, Dylan unleashes a mighty howl of desperation, his finest song of the era. When he says "Be easy, baby, there ain't nothing worth stealing in here," it's the late-night Zen croak of a flophouse sage. Also, a video where he tries to line-dance. The man had a lot of crazy ideas in those days.
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