“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.
The 100 Greatest Artists of All Time: Bob Dylan
“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.
“Pretty Boy Floyd” (Folkways: A Vision Shared — A Tribute to Woody Guthrie and Leadbelly, 1988)
Dylan gave many shout-outs to Woody Guthrie over the years, most directly in this cover from the tribute album Folkways: A Vision Shared, reviving the outlaw tale that helped inspire classics like “John Wesley Harding” and “Drifter’s Escape.”
“Tweeter and the Monkey Man” (The Traveling Wilburys, Traveling Wilburys-Vol. 1, 1988)
If only he’d done a whole album of these, instead of the actual albums he was grinding out at the time. This shaggy-dog hippie tale (from the Traveling Wilburys album) has all the wild humor of Thomas Pynchon’s Vineland, goofing on Bruce Springsteen, Neil Young, the Sixties and — most of all — Bob Dylan.
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“Born In Time” (Under the Red Sky, 1990)
Yet another Oh Mercy outtake. He fumbled the song on the atrocious Under the Red Sky, but this definitively gritty version eventually came out on Tell Tale Signs.
“Blood In My Eyes” (World Gone Wrong, 1993)
The highlight of his pivotal voice-recovery project of the early Nineties, turning blues and folk oldies into the sound of a brand new Dylan growl. He captures the wit of the Mississippi Sheiks’ 1931 original, but adds his own sly menace as he purrs, “Hey babe, I got blood in my eyes for you.”
“Series of Dreams” (The Bootleg Series, Vol. 1-3, 1991)
The conceptual centerpiece of Oh Mercy. Except in the tradition of “Blind Willie McTell” and “Caribbean Wind,” Dylan left the centerpiece off the album.
“She’s Your Lover Now” (The Bootleg Series Vol. 1-3, 1991)
“Pain sure brings out the best in people, doesn’t it?” Sure does, Bob. Mr. Charm shows off his sparkling personality with six minutes of mega-bitch ice-queen putdowns, spewing enough venom to make Andy Warhol’s Factory scene look like sarcasm amateurs. Even the guys in the Band must have felt a little uneasy at the moment when Dylan sneers, “You just sit around and ask for ashtrays. Can’t you reach?”
Bob Dylan’s Late-Era, Old-Style American Individualism
“Standing in the Doorway” (Time Out of Mind, 1997)
It’s easy to forget, because of all the other millions of things Dylan does, but he sure does write great brooding woman-loss songs. His voice here sounds even more bereft than Auggie Meyers’ organ.
“Nettie Moore” (Modern Times, 2006)
A change of pace on Modern Times: a stately tribute to nineteenth-century parlor piano ballads, more Stephen Foster than Muddy Waters, with Dylan claiming, “I’m the oldest son of a crazy man / I’m in a cowboy band.”
“Dreamin’ of You” (The Bootleg Series, Vol. 8: Tell Tale Signs, 2008)
Another standout from Tell Tale Signs, this one cut for Time Out of Mind, recycling lyrics from “Standing in the Doorway.” Dylan plays a lonesome fugitive, trailing a woman who’s an even craftier fugitive than he is.
“Huck’s Tune” (The Bootleg Series, Vol. 8: Tell Tale Signs, 2008)
From the soundtrack of the barely noticed Drew Barrymore film Lucky You, saved for posterity on Tell Tale Signs. It’s a slow-burning romantic blues: “When I kiss your lips the honey drips / But I’m gonna have to put you down for a while.”