Visions of Johanna (from Blonde On Blonde)
This is probably the first Dylan song I remember being aware of specifically as being by “Bob Dylan,” as introduced to me by my high school friend Jeff, who once played “Maggie’s Farm” at the talent show. I remember having a conversation late one night with some girls who went to Scripps College about how a guy one of them brought home the weekend before was just like “little boy lost” – bragging of his misery.
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Tombstone Blues (Live version. Original version from Highway 61 Revisited)
It took me a long time to realize that Stephen King was quoting from this song in “The Stand” when his character Donald Merwin Elbert, better known as “The Trashcan Man,” acknowledged the inevitability of prison sex: “You didn’t die…it wasn’t poison.”
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It’s All Right Ma (I’m Only Bleeding) (from Bringing It All Back Home)
I love that the title phrase is never actually uttered in the song.
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Desolation Row (from Highway 61 Revisited)
This is my absolute favorite Dylan song. The continually shifting guitar riffs, and the seemingly endless parade of meandering, poetic images and characters is, in my mind, Dylan at his finest. I once wrote a set of alternate lyrics for this song after a bad breakup and submitted it as an assignment in one of my classes. The professor, an incredibly nice man, took pity on me and gave me a passing grade – even though the class was Demilitarizing Science and Technology in the L.A. Basin.
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Jokerman (from Infidels)
The opening song from 1983’s Infidels was a stepping stone between Dylan’s much maligned Christian period and a return to “secular” writing. With both biblical and classical imagery, Dylan subtly rails against the social construct that leaves men distracted from the knowledge that allows them to see or do what is right with consumption and false idols: “Freedom just around the corner for you / But with the truth so far off, what good will it do?” As a side note, Wyclef Jean says that this is one of his favorite songs of all time, and as a preacher’s son, the lyrics had an extreme impact on him when he first heard it.
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Blind Willie McTell (from Bootleg Series Vols. 1-3)
This song, written and recorded in 1982 but not released until seven years later, became infamous just for being left off the Infidels album. Producer Mark Knopfler was shocked that Dylan wasn’t happy with the result, and indeed, though Dylan has gone on to perform it in concert, the live arrangement is often a more plodding, electric dirge, especially compared to the stripped, airy, piano and acoustic guitar arrangement from the studio session. As for the quality of the song–it’s simply amazing, and one of the first moments that shows Dylan fully becoming the type of traditional American songster that influenced him, and that he himself would fully morph into in the 1990s.
Most of the Time (from Oh Mercy)
The first song on the second side of Dylan’s best album of the 1980s: Oh Mercy. This song is a straightforward yet devastatingly delivered series of thoughts on the fallout from a dead relationship, with the narrator’s attempt at confidence and stability cracked by the song’s title coming back again and again. The spooky atmosphere that producer Daniel Lanois gives the proceedings-via an echoed wall of keyboards and a rhythm section that sound like is was recorded at the bottom of a well-only adds to the dark, effective mood of the piece. Dylan’s low growl during most of the song’s delivery is also perfect.
I’ll Keep it With Mine (from Bootleg Series Vols. 1-3)
I prefer this unfinished version to the complete, piano-only take on Dylan’s Biograph box set. It doesn’t just show a work in progress, it shows an arrangement coming together live in the studio, and once the arrangement “clicks” halfway through (lightly brushed snare drum, swirling organ, pulsing tack piano) the results are gorgeous. It’s a shame that they didn’t do one more take with the final arrangement and put it on Blonde on Blonde. There was still some room available on side four.
Shooting Star (Live version. Original version from Oh Mercy)
The same album side that opens with “Most of the Time” ends with “Shooting Star”, a song that manages in just over three minutes to be both sad and beautiful, hopeful and apocalyptic, personal and universal. In other words, classic Dylan.
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The Man In Me (from New Morning)
“The Man in Me”, from the 1970 album New Morning, one of the few high points during Dylan’s first truly fallow period (lasting from 1969 to 1974), is at first glance a simple love song; but the subtext reveals Dylan’s continuing feelings about the image of him in society, and his justification of the low profile he continued to take after his 1967 motorcycle crash. It would take Dylan’s friend and future bandmate George Harrison to drag him back into the public eye a year later for the historic Concert for Bangladesh.
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We Just Disagree (live Dave Mason cover)
When Dylan became born again at the end of the 1970s and went on tour, the reaction he got was borderline hostile at some places, where people expected that even a Dylan who’d been “saved” would perform a “standard” show full of greatest hits. Instead, what they got were almost all Christian songs and preaching from the stage. One of the worst responses was in San Francisco. So it was of some note that when Dylan returned to the Bay Area a year later, he performed a less religious set, even including a superbly arranged cover of Dave Mason’s “We Just Disagree”. What the crowd may not have realized, though, in amongst the soulful arrangement and the female background singers, was the more esoteric statement that Dylan was making. Yes, he seemed to meet them halfway, but the lyrics, bespeaking a tale of dismissal mixed with co-dependency, basically said “I’m going to believe what I want, and you’re going to believe what I want. You get the tunes now, but you won’t get your soul saved.”
Girl From the North Country (from The Freewheelin’ Bob Dylan)
Based somewhat on the traditional English song “Scarborough Fair”, this song showed Dylan had the ability to write classic, complex love songs. Perhaps most importantly, this song features one of Dylan’s greatest vocals. Yes, he may not have ever had a “great” singing voice in the traditional sense of the word, but the man could express emotion at times like Sinatra. If anyone tells you Dylan couldn’t sing, put this one on, and watch them shut up.
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Masters of War (from The Freewheelin’ Bob Dylan)
Coming directly after “Girl from the North Country” on The Freewheelin’ Bob Dylan, this is still one of the most devastating political songs ever written. And, while Dylan sometimes gets unfairly lumped in with the peace and love generation, this song smashes that concept to bits. Unlike most other folkers, Dylan is much more Malcolm X than Dr. King in this song. He doesn’t want resolution, he wants an eye for an eye: “And I hope that you die / And your death’ll come soon….And I’ll stand o’er your grave / ’Til I’m sure that you’re dead”.
License to Kill (from Infidels)
From Infidels, we have an underrated Dylan classic here, and another indictment of man’s behavior, this time focusing more single-handedly on his more gluttonous preoccupations, not striving for self-sufficiency, but being trained to do acquire as much as possible by society just because you can, and as though doing so it is right and necessary. Dylan said in a mid 1980’s Rolling Stone interview that while he didn’t know what he wrote the line, he truly believed this song’s couplet “Oh, man has invented his doom / First step was touching the moon”.