Bob Dylan’s 20 Best Songs of the ’80s

Bob Dylan sounded lost in the 1980s. The times had a-changed considerably since he had been anointed the spokesman of a generation, and the onetime visionary struggled to adapt to a musical landscape that had been reshaped by punk and synth-pop, MTV and hip-hop. At times, it appeared Dylan had lost his vision entirely, writing limp and uninspired songs or smothering decent tunes in slick and gaudy production. And sometimes he would record something that could go toe to toe with his past classics—“Blind Willie McTell,” “Series of Dreams”—only to keep it to himself. Just about everyone agrees that the ‘80s were the low point of Dylan’s legendary career: the only point of contention is when, exactly, he hit bottom. (This writer says 1986, when Dylan not only dropped Knocked Out Loaded but contributed a rap verse to Kurtis Blow’s “Street Rock.”)

And yet, you could make the argument that the ‘80s were Dylan’s most underrated decade—which is to say, still his worst, but not nearly as bad as you’ve heard. It was a rough decade for many of rock ‘n’ roll’s essential figures, but unlike David Bowie (who spent it desperately chasing hits) or Neil Young (who spent it antagonizing his fans and label), Dylan at least tried in earnest to bring his music into the present. He enlisted a myriad of new collaborators to help him write, record and—most importantly—produce his songs. He continued his experiments with gospel, and incorporated elements from other genres like reggae and glossy ‘80s pop. He made a few music videos, and managed to not make himself look like a total doofus. He joined forces with George Harrison, Tom Petty, Jeff Lynne and Roy Orbison to form the Traveling Wilburys, a supergroup that actually lived up to the hype. He was, for the most part, fundamentally unwilling to rest on his laurels, to revisit Highway 61 Revisited or Blood on the Tracks, longtime fans be damned.

Even though Dylan missed as much as he hit in the ‘80s, he was still batting a higher average than almost anyone else in his boomer cohort. And—let’s not sugarcoat this—Dylan’s misses were truly catastrophic: the three albums he released that decade with no representation on our list are widely regarded as three of the absolute worst albums in his discography. But every now and then, those listeners who remained faithful were rewarded with songs that, if only for a moment, reminded them why they fell under Dylan’s spell—“Every Grain of Sand,” “Jokerman,” “Ring Them Bells.” And at the end of the valley of the shadow of the ‘80s, Dylan made Oh Mercy, one of his strongest collections of songs since his zenith in the 1960s.

So come gather ‘round, people, wherever you roam, and admit that the reputation of Dylan’s ‘80s output has grown. Let these 20 songs be your entry point into Dylan’s most challenging and most overlooked period. – Jacob Nierenberg

“Heart of Mine”

Dylan can be acerbic and tender in equal measure. “Don’t Think Twice, It’s Alright” is an early example of how these two qualities mix – somehow leaning on the old line “it’s not you, it’s me” while expressing genuine regret. Even the tongue-lashing of “Idiot Wind” is tempered with self-criticism. But Dylan still barks as he licks his romantic wounds. Not so much on “Heart of Mine.” Here, Dylan lays out hard-won wisdom, turning his exacting lens inward. The song pulls from the Old Testament, taking Jeremiah 17:9 as a kind of mantra: “The heart is deceitful above all things, and desperately wicked; who can know it?” While Dylan alludes to the potential for infidelity on the part of the unnamed love-interest, it’s just a ploy to keep his heart reined in before, in the final verse, reworking scripture to pass verdict on himself.

The instrumentation of Dylan’s honky-tonk piano playing, Ronnie Wood’s funk-inflected guitar and Ringo Starr’s serviceable beat-keeping shouldn’t work. In fact, Dylan was not particularly fond of the album version, calling his choice of this cut “perverse.” Fans have tended to prefer the various alternate or live cuts that circulate. But there’s something about the album version that elevates it above the one that appeared on Biograph (too fast) and the outtakes floating around on the internet (too slow). Maybe it’s even Ringo. The song’s rhythmic complexity relies on where Dylan inserts the vocal line, and Ringo is a smart enough not to overwhelm the track. Maybe it’s Wood, who fills the pockets between Dylan’s vocals with just the right amount of flavor. Or maybe it’s the uncredited backup singer who might be Dylan’s infamously secret wife who he would not marry for another five years. It’s not impossible that Dylan chose this cut due to her presence, whether he knew it or not – it might just be the thing that makes this song one of Dylan’s best. – Ian Maxton

“The Groom’s Still Waiting at the Altar”

In a typically contrary move, one of the best songs on Shot of Love wasn’t even on the original album. “The Groom’s Still Waiting at the Altar” originated as a B-side to the single release of “Heart of Mine,” which may make it the definitive Dylan 45 of the ‘80s. Though included on the cassette, CD and LP versions of Shot of Love from 1985, you will not find “Groom” on the original vinyl pressing.

Dylan wrote “Groom” in the aftermath of a failed relationship with Mary Alice Artes, an African American actress who was one of the reasons Dylan found Christ in the first place. He likes to tell the story of somebody throwing a cross on stage, but there was a more worldly path to Jesus. According to Michael Gray’s Bob Dylan Encyclopedia, Artes, after she converted to Christianity herself, refused to keep living with Dylan in sin.

If you believe the lyrics, her fervor waned. Dylan wrote “Groom” not long after he’d presented Artes with an engagement ring worth $25,000, and his response to rejection wasn’t pretty. If in this version he merely suggests that “Claudette” might have ended up as a streetwalker, early lyrics leave no doubt that, after abandoning him, she resorted to turning tricks.

With its shuffling, thick wild mercury sound vaguely updating “Highway 61” for ‘80s production values, “Groom” sounds like the perfect marriage between the young brat and the seasoned professional. Its lyrics hint at apocalypse and are set to an irresistible barroom beat. Invoking the ancients, “West of the Jordan, east of the Rock of Gibraltar” delivers a biblical pinpoint to a wailing slide guitar. Dylan sounds so raucously engaged here—listen to him draw out “Gibraltaaaar” in the third chorus—that’s not the sound of somebody phoning it in; it’s a newly inspired veteran. Inspired by…Whom? This is pure rock ‘n’ roll fun, but it’s also a biting rebuke; “I see the turning of the page/ Curtain rising on a new age/ See the groom still waiting at the altar” he chastises Claudette—or Artes. Even when Dylan sounds like he’s just peeling off another essential rocker, there’s a whole world of meaning behind it, and here’s it’s fueled by no less than the eternal struggle between bodily desire and God. – Pat Padua

“Every Grain of Sand”

Dylan’s so-called “Christian trilogy” of albums – Slow Train Coming (1979), Saved (1980) and Shot of Love (1981) – were famously reviled by fans and critics alike upon their release. Though at least one of those groups have since warmed to that era’s material, there remains a notion, which I wrongly used to share, that something fundamental went awry when Robert Zimmerman started preaching the gospel.

One track, from the final entry of Dylan’s triptych, was heralded back when those LPs remained deeply unfashionable: Shot of Love’s concluding hymn, “Every Grain of Sand.” Critics called it “sublime” and compared it to the likes of “Blowin’ in the Wind,” “Chimes of Freedom” and “Mr. Tambourine Man.” Bruce Springsteen and Elvis Costello sang its praises. Emmylou Harris (who’d previously recorded a cover on a celebrated album) performed it with Sheryl Crow at Johnny Cash’s funeral.

If you listen to “Every Grain of Sand” out of context, without the baggage of who fans and critics thought Dylan should be in the early-’80s, you can hear how much it points to later, universally renowned material. Add some tobacco gravel to his voice, and the song could have appeared on Time Out of Mind as a sibling to the aching mortality of “Not Dark Yet.” But that nicotine scratch hadn’t yet arrived when the song was put to tape. There’s a purity to Dylan’s vocal instrument, the sweet spot between his middle and late periods, so evocative and yet increasingly bruised.

The song is ultimately a bridge, a return to the secular from the sacred. Dylan pulls apart the metaphysical curtains, singing about the “hour of [his] deepest need”, wading through “pools of tears” and “hanging in the balance”. He’d revisit such themes in compositions to come, but Jesus (who’s barely mentioned, here, as it is) would become conspicuously absent from his subsequent works, a pivot that was met with few objections. – Peter Tabakis

“Caribbean Wind”

“Caribbean Wind” – the most beguiling and vital work of Dylan’s “Christian” period – never made it on a studio album, positioning it outside the neat lines of canonization. Sure, there is a version on Biograph, a strange twist on the Greatest Hits as only Dylan could deliver it. Kicking off disc 3, the only people outside of Dylan’s circle who had heard the song before then would have been in attendance at a show on 11/12/1980 – the single time the track has been played live. That version was elevated to “official” status via the Bootleg Series volume Trouble No More. Elsewhere on that set is yet another version with a lovely pedal steel. And if you search the web, you’ll find yet another recording, this one from the Shot of Love sessions.

Across versions, the lyrics morph, as if Dylan is trying to reconstruct a dream. Even the official lyrics on Dylan’s website are different from any recorded version. The song partakes of that same surreal stream as “Desolation Row” or “Changing of the Guards,” made all the more strange by the impossibility of pinning it down. Like a lot of Dylan songs, it starts with a woman – a figure that pulls him into an Otherworld – but her attachments are ambiguous. She might be a spy or a revolutionary, a demon or an angel. In some versions, men “practice the hoax of free speech,” in other versions they celebrate that right. Time melts as Dylan tours from city to city. In one, he finds himself in bed with his double. In them all, apocalypse and uncertainty loom: “Every new messenger brings evil report/ ’Bout armies on the march and time that is short/ And famines and earthquakes and hatred written upon walls.” Ships roll over iron waves to bring an end to all the speaker holds dear. The only constant is that Caribbean wind, blowing to and from an ever-changing list of places.

Dylan never felt he got the song quite right, lyrically or musically. But what we are left with is a kaleidoscopic work, made all the more interesting by the liminal space in which it has been (fittingly) left to reside. – Ian Maxton

“Jokerman”

Leaning on a reggae bass-line and filigreed by Mark Knopfler’s guitar licks, “Jokerman” may seem an unlikely successor to “Mr. Tambourine Man” – chief among the many shamanic figures standing watch over Dylan’s oeuvre – but it’s perhaps the strongest evidence available that Dylan continued to operate at another level long after fans and critics had marked him as having fallen off. Lyrically dense, the song’s central figure could be King David, or Christ, or a re-working of the racist medieval trope of the Wandering Jew – it could even be Dylan himself. It’s probably all and none of them. But it is unquestionably a song about what it is like to live in history. “Men make their own history, but they do not make it as they please.” That sounds like Bob Dylan, but it’s Karl Marx. Maybe the song’s about him, too. Images and figures and events flash by as the Jokerman watches over. By the time Dylan sings the rhythmically charged lines, “Nightsticks and water cannons, tear gas, padlocks/ Molotov cocktails and rocks behind every curtain,” it arrives like a shock to the listener in much the same way as these things do in real life. You’re either called to action, or you recoil in fear.

Capturing that prophetic fire of the track, Dylan showed up on Letterman during this period with a one-night-only band of L.A. punks and played a blistering, righteous version of the song that ranks among his best-ever live performances. The emergence of that performance online is one of the reasons why Infidels has rightfully been re-evaluated in recent years. Vampire Weekend even play a tasty, jammy version of “Jokerman” at their live shows these days. As good as the album is though – and I’m a partisan – there is a glimpse of something on that Letterman performance that can’t help but leave one wondering what it would have been like to see Dylan go Punk. But that, too, is what it’s like to live in history: to see only shadows down past roads not taken, impassable now, and to be offered a future with even less certainty – but one toward which we must move inexorably. – Ian Maxton

“I and I”

The most striking thing about Infidels as an album is how readily it does a 180 from the two albums that preceded it. Obviously, these songs are secular as opposed to the gospel of Saved and Shot of Love, but there’s also a bitter, cynical streak to songs “I and I” that is a bit striking considering the headspace Dylan was in only a few years prior to recording these songs. It’s tempting to look at “I and I” as a lyrical throwback to the despondent, lovelorn heroes that Dylan cast himself as on Blood on the Tracks, but a deeper dive finds something darker, more harrowing and inseparable from his spiritual reawakening. After spending a few years celebrating God, the Dylan of “I and I” portrays a lost world where casual cruelty and aimlessness are commonplace.

“I and I” feels like the most personal song on Infidels, an album not exactly known for Dylan cutting to the core of his or our very souls. Indeed, he feels very much present in the song, rather than playing the part of a detached narrator. Rather than use the deeply personal language that he used in his ’70s work, though, Dylan’s words take on a broader tone that still feels spiritual to some degree. He invokes King David and Hammurabi in the verses, and the chorus line “I and I/ In creation where one’s nature neither honors nor forgives” feels more philosophical than grounded. In that sense, “I and I” maintains the throughline of Dylan’s newfound faith; it just finds him focusing on fire and brimstone as opposed to clouds and seraphim. – Kevin Korber

“Don’t Fall Apart on Me Tonight”

The narrative structure of the song itself is interesting in that Dylan begins his case for reconciliation with a lover by trying to appeal to her better nature, asking what it is she hopes to achieve by leaving, asking if they can’t talk about it some more and finally attempting to instill fear by intimating in no uncertain terms that the outside world is an incredibly dangerous place. By the chorus, he’s moved on to a sort of passive-aggressive bit of pleading, employing the title phrase before offering up the ambiguous “Yesterday’s just a memory/ Tomorrow is never what it’s supposed to be.”

It’s the final line of the chorus, however, that unequivocally places “Don’t Fall Apart on Me Tonight” into the realm of a Bob Dylan love song. “And I need you, yeah,” Dylan finally offers up, forgoing the grandiosity of the first verse and sentiments of the first half of the chorus. The second verse finds him reflecting on his life’s decisions, reckoning that, had he gone a different route, they wouldn’t have found themselves at the current relationship crossroads. This move from pleading to accepting blame to, by the final verses, rational plea for honest conversation and relationship analysis makes this a love song of the intimately interpersonal variety.

This reversal of tactics in attempting to get his lover to stay shows either a deep propensity for honest change upon self reflection or some truly sociopathic behavior, twisting the narrative in various ways to see what lands hardest and proves most successful in getting his lover to stay. Offering up the idea that yesterday is really and truly in the past – nothing can be done at this point about memories – and that whatever the future holds is never really what we hope and plan for it to be is the final attempt at reconnecting: What’s done is done, and nothing ever goes the way it should despite our best efforts to the contrary, but the fact of the matter is I need you in my life. At least until the next bump in the road. – John Paul

“Blind Willie McTell”

Why did Bob Dylan exclude one of his all-time finest compositions from the 1983 secular-comeback album Infidels? This remains one of the great unanswered questions of his multi-decade career. “Blind Willie McTell,” which pays homage to a lesser-known blues singer, is unique in Dylan’s canon. He’d previously lionized other immortal artists (Woody Guthrie, Lenny Bruce), and protested the brutality experienced by Black Americans (“The Lonesome Death of Hattie Carroll,” “Hurricane”). “Blind Willie McTell” does both at once, with an overwhelming sigh.

Celebration and outrage combine seamlessly here. Dylan offers a tender encomium to the title virtuoso and also recounts the original sin of American slavery. These two threads weave, inseparably, into a splendid aural tapestry. The song is as emotionally moving as “Don’t Think Twice, It’s All Right” and “It’s All Over Now, Baby Blue.” By the final verse, it matches the righteous bile of “Like a Rolling Stone” and “Idiot Wind.”

“Blind Willie McTell” stands as a six-minute repudiation of any argument that somehow insists Dylan’s ‘80s output was fallow. The song, with its spare and dramatic piano backbone by Dylan himself, accented with Knopfler’s haunting guitar notes, seems performed in an open field at midnight. The tableau is as cinematic as Dylan gets. An arrow swings on a doorpost. An owl hoots. Feathered maidens strut. Martyrs fall. A canopy of stars hovering over “barren trees” transforms into an uproarious crowd.

At the very top is the unnamed Maker, who watches over us all. We all, apparently, covet “what’s His.” Dylan used to sing His praises, but now can only recall a simple couplet, a newfound mantra: “Nobody can sing the blues/ Like Blind Willie McTell.” – Peter Tabakis

“Someone’s Got a Hold of My Heart/Tight Connection to My Heart”

Dylan has long spent hours revising and recasting his own work. Sometimes he got in his own way, which is what happened with a song that originated as an Infidels outtake and reemerged in wildly different form on Empire Burlesque.

The 1985 release “Tight Connection to My Heart (Has Anybody Seen My Love)” is catchy enough. With gospel-tinged backup singers and a distinctly ‘80s drum sound, it’s one of Dylan’s most hummable of the decade. But the lyrics seem like throwaways, and there’s a reason—much of it is borrowed. If “Mississippi” skillfully appropriates a prison song from Parchman Farm, these are less promising sources, from The Maltese Falcon and even a “Star Trek” episode.

The Bootleg Series release of “Somebody’s Got a Hold of My Heart,” one of 13 takes of the song Dylan recorded in 1983, reveals a more personal sentiment, and it’s one of his most affecting ballads of the era. It’s a gentle shuffle, Dylan’s wistful harmonica playing over acoustic rhythm guitar that recalls Lou Reed’s equally naked “Coney Island Baby.” The lyrics here hit some of the mystical elements Dylan fans love to parse; he references everything from Madame Butterfly to standards like “September Song,” he talks about Babylon and beating the devil. But what stands out is the plainspoken chorus and its atypically sweet delivery: “Someone’s got a hold of my heart/ You, you, you, you/ Yeah, you got a hold of my heart.” Contrast this with the 1985 chorus, “Has anybody seen my love,” which isn’t nearly so vulnerable.

For most of his career, Dylan has had a reputation for expanding the language of rock to a visionary verse. Here, he’s inspired to communicate in the primal essence of pop music, the love song. The boy genius, now middle-aged, shed the mental pyrotechnics and for a moment got so directly tender, all in the middle of a decade known for over-production. Maybe he was afraid to reveal himself as such a simple man at heart, but you wish he’d managed a whole album in this mode. – Pat Padua

“When the Night Comes Falling from the Sky”

Bob Dylan singing with members of the E Street Band sounds exactly like you might expect—and thank God for that. The clarity of the production on this outtake illuminates just how good “When the Night Comes Falling from the Sky” is—you’d be forgiven for missing this on the Empire Burlesque version, which suffers not so much because of the dated ’80s dance sound as because of the way that sound obscures the lyrics and the fiery, prophetic power of Dylan’s vocal. The jarring quality of the Empire Burlesque version makes sense when you consider that Dylan originally conceived this as a rock song before he and Arthur Baker turned it into a dance track (the version with Steven Van Zandt and Roy Bittan is the earlier version). Great lines like, “I don’t want to drown in someone else’s wine”—if you can even hear them—sound hollow on Burlesque, whereas here they resonate unlike any Dylan track before or since.

Even at his most rock ‘n’ roll, Dylan rarely made tracks of Springsteen’s gargantuan proportions (as much as Springsteen himself wanted to be Dylan), but here, as on a few select tracks from elsewhere in his catalogue (“Changing of the Guards,” “Shot of Love”), we see a glimpse of a Dylan that turned up the theatrical bombast a little. Dylan’s ’80s output doesn’t get enough credit for being fun, and this version of “When the Night Comes Falling from the Sky” is one of his most instantly pleasurable songs in any period. With Springsteen’s legendary band behind him, you’ve got a version that lets the songwriting, always Dylan’s greatest strength, shine. The only downside is it makes you wish you could hear Dylan sing alongside Van Zandt more often. – Tyler Dunston

“Dark Eyes”

Let’s be honest: for a lot of people who hate Dylan’s 80’s material, the production is the biggest roadblock. Hearing Dylan’s gruff, ramshackle voice alongside the polished, staid guitars and gated drums that were the decade’s sonic hallmarks is jarring, to say the least. For those Dylan fans, “Dark Eyes” had to be an oasis in a musical desert. Even as Empire Burlesque has relatively risen in stature among some critics in fans, it remains a real highlight in Dylan’s oeuvre as a whole.

To hear Dylan tell it, “Dark Eyes” more or less happened by accident. In his memoir, Dylan recalls having the concept of a spare, acoustic song as an album closer in mind, but that the lyrics didn’t come to him until he met a woman at a hotel later that evening. The story Dylan tells is laced with tragedy; he recalls the woman wearing heavy eye makeup, perhaps to hide that she had been abused. That tragedy plays out in “Dark Eyes,” which appears to be about fleeting existence, as Dylan weaves disparate images together, jumping from verse to verse. Still, no matter where Dylan takes us, we return with him to the same resignation: “All I see are dark eyes.”

Musically, this is as simple as Dylan gets. The song was put together quickly, and it kind of shows both in the sparseness of its arrangement and the rudimentary structure. The simplicity of “Dark Eyes” arguably works in its favor. In a decade where Dylan seemed more and more in danger of getting lost in the studio, it serves as a reminder of where Dylan came from and what kind of songs he could still write. – Kevin Korber

“Death is Not the End”

Though widely reviled as one of Dylan’s worst studio records, his 1988 album release did yield some decent tracks. Dylan needed a hit record following Knocked Out Loaded, yet Down in the Groove suffered a tortured history of delays, shuffled track running orders and a large number of collaborators that even included the Grateful Dead.

The lack of cohesion likely springs from the fact that none of the songs on Down in the Groove were recorded at the same session. Coming near the middle of the album, “Death is Not the End” finds Dylan musing about what happens after we die. Co-produced by Mark Knopfler, it was actually written and recorded back in 1983, around the time of Infidels. Featuring Knopfler on guitar and Robbie Shakespeare on bass, the song was supposedly recorded in one take.

Much of the song follows a similar vein with Dylan intoning lines such as, “When you’re sad and when you’re lonely, and you haven’t got a friend/ Just remember that death is not the end/ And all that you’ve held sacred, falls down and does not mend/ Just remember that death is not the end.” Most of the song follows the pattern as Dylan as casually drops references to cities on fire with the burning flesh of men, except one refrain where the song crescendos and Dylan cries, “Oh, the tree of life is growing/ Where the spirit never dies/ And the bright light of salvation shines/ In dark and empty skies.” Though he is well out of his Christian period in the late ‘80s, the lyrics hear harken back to his work on Saved.

If anything, “Death is Not the End” is better known for the superior version Nick Cave recorded in the mid-‘90s for Murder Ballads. Featuring vocals from PJ Harvey, Blixa Bargeld, Shane MacGowan and more, Cave cashes in on the song’s full potential. Dylan, the shepherd, provided the blueprint, Cave, the disciple, created the masterpiece. – David Harris

“Silvio”

In 1988 even Dylan seemed to think his best was behind him. Yet if “Silvio” lacks its creator’s signature genius (Grateful Dead lyricist Robert Hunter wrote the lyrics, after all), it’s still great pop, and oddly prescient.

And oddly relaxed. Dylan was nearing the end of an erratic decade, but he sounds so at ease here, and “Silvio” would become a staple of live shows—he reportedly played it 99 times in 1998 alone. The easy-going shuffle is to prime Dylan as “Touch of Grey” is to prime Dead. But its cheery demeanor is a screen for some perceptive lyrics from Hunter, starting with the opening line: ”Stake my future on a hell of a past..” Remember, this was on an album that consisted of mostly covers like Wilbert Harrison’s “Let’s Stick Together.”

You don’t have to dig far to discover that Dylan’s ease plays against some dark lyrics. For instance, what of that chorus? “Silvio/ Silver and gold/ Won’t buy the beat of a heart grown cold.” Dylan (through Hunter) echoes his Christian period with what seems to be a tale of a man too old to sell his soul to the devil. His fervor gone, he would like nothing better than to sell his soul for another shot, but it’s too late. “Silvio/ I gotta go/ Find out something only dead men know.” It’s a sentiment worthy of Harry Smith’s Anthology of American Folk Music; Dylan seems to be singing about his own future, when, facing mortality, he will hit his late-career stride. Even in his diminished genius, Dylan could convey with the most benign earworm a profound commentary on his own compromised state—and look far into a future still decades away. — Pat Padua

“Everything is Broken”

Is there really a better anthem for 2020 than this? “Broken idols, broken heads/…Streets are filled with broken hearts/ Broken words never meant to be spoken/ Every time you leave and go off someplace/ Things fall to pieces in my face.” And while it was originally penned as a very personal examination of the feelings of loss and general disaffection, there is likely not a one of us who, this year, hasn’t been able to intimately relate to at least one of the lines in “Everything is Broken.”

But despite the seeming universality of the song’s sentiments today, it is at its heart a blues designed to resonate with those experiencing any of its broken items and ideas. Like all good and resonant blues lyrics, “Everything is Broken” is general enough to apply to nearly any feeling of despondency. In this, Dylan is going back to his folk and blues roots three decades into his storied career. “Seems like every time you stop and turn around/ Something else just hit the ground” could well be the song’s most autobiographical passage as Dylan seems to take stock of his life and career at that particular point in the late-‘80s.

Taking this literally, it could serve as an answer to why Dylan continues to write and tour well into the 21st century: Were he to stop and take stock of everything in his life, the various moving parts and pieces could start to come undone, the mythology crashing in on itself. Or it could just be another in a seemingly endless catalog of choice lines and phrases that can be appropriated in any way the listener (or, in this case, writer) sees fit. Based on producer Daniel Lanois’ recollections of the Oh Mercy sessions, any amount of thought we put into such analyses is still less than Dylan did himself. – John Paul

“Ring Them Bells”

Bob Dylan has lived most of his life in an apocalypse. Maybe that’s why he’s a modern day revelator. His ’80s began with the end of his Christian rock phase, but the line of thinking persisted–not that Biblical imagery was new territory for the songwriter. With Oh Mercy‘s “Ring Them Bells” Dylan stepped deep into spiritual waters, with churches and saints and holy tintinnabulation. Across a sacred piano and plenty of Lanois-produced void, Dylan sings of St. Peter (possibly the person and the basilica) and proclaims the end of time, liberation for the poor, healing for the blind and deaf. In the world of the song, judgment comes to right the world, and Dylan peaceably watches it come in.

Or does he? The song’s opening line betrays the complication: “Ring them bells, ye heathen.” The line would startle if it weren’t so gentle, but it only becomes truly weird as the song progresses, with its call to ostensibly Christian people and imagery. The trick, though, comes less through the addressees (heathens, saints and possibly listeners) than through the world around the singer. It’s “on its side” and “the shepherd is asleep.” The earth isn’t ripe for the harvest or church-y celebration; it’s a mess, and Dylan, despite his cool, doesn’t clarify who comes to save it. He doesn’t relinquish his transcendental yearnings, but he doesn’t make them easy for us. The complexity itself hints at the solution: until the shepherd wakes, until the deaf hear and the blind see, we (the unaddressed bell-ringers of verse four) have work to do. The bells, it turns out, chime in both alarm and celebration, the expression of alarm and the hope for resolution. After all, we can consider the lilies from our fortress, but we still need to comfort the crying child. – Justin Cober-Lake

“Most of the Time”

Dylan devoted nearly 80 pages of Chronicles, Volume One to the recording of Oh Mercy, and all of two paragraphs to its best song, “Most of the Time.” “It was all dammed up and stagnant,” he wrote. “The song, which seemed unfinished to begin with, had just become more unfinished as we rolled on. I wondered what I had gotten myself into.” Dylan’s autobiography is a vexing—and almost certainly embellished—document, and its author would much rather tell unverifiable tales about the characters he met on a motorcycle ride through rural Louisiana than offer any meaningful insight into his creative process. Then again, “Most of the Time” is almost like a magic trick in that any attempt to detail its creation would break its spell.

The party line about Dylan in the ‘80s is that he just couldn’t pick the right producer, and at first blush, Daniel Lanois (who had previously collaborated with U2, Brian Eno and Peter Gabriel) looked like the most intriguing mismatch yet. Lanois cloaks Dylan in ambient clouds of guitar, as warm and humid as the New Orleans spring the album was completed in, and lets Dylan’s words unfold patiently. An early take shows how it could have sounded like a folk lament, but awash in Lanois’ production, “Most of the Time” practically becomes a hymn, as awe-inspiring as “Every Grain of Sand.”

It can be heard as a long-delayed coda to Blood on the Tracks, Dylan’s supposed “breakup album.” Just as Dylan was in denial about the songs he wrote for that album being allusions to his own crumbling marriage, the singer here is in denial about his ongoing heartbreak, and the façade gets more and more transparent with every passing verse: “I don’t even notice she gone,” “I don’t even think about her,” “Don’t even remember what her lips felt like on mine,” “I don’t even care if I ever see her again.” And every time, he undercuts those claims with the song’s title, making it clear that the rest of the time, she’s all he can think about. It’s over, “Most of the Time” all but implies, but you’re not over it. – Jacob Nierenberg

“What Good Am I?”

At the tail end of the ’70s, Dylan told a crowd of fans, “You know we’re living in the end times.” Going on to incorporate his past political songcraft into a new religious context, “I told you ‘The Times They Are A-Changin’ and they did. I said the answer was ‘Blowin’ in the Wind’ and it was.” On “Slow Train,” Dylan sang about retribution like a prophet of Armageddon. It rubbed many of his fans—particularly those who were drawn to the very different moral voice of his early ’60s material—the wrong way. Rather than songs of mercy and identification, some songs of this period seemed to stem from a sense of alienation with the world, desire for something beyond and for retribution. By the end of the ’80s, however, most notably on “What Good Am I?,” Dylan turns that moral voice on himself, sparing himself nothing as he speaks with a directness and plainness which is a big part of Oh Mercy’s charm.

On this post-Christian period track, Dylan ironically embodies scripture: “And why beholds thou the mote that is in thy brother’s eye, but considers not the beam that is in thine own eye?” Ten years previous, he sang, “Sometimes I feel so low-down and disgusted” and wondered what was happening to “[his] companions.” On “What Good Am I?,” he lumps himself in with the fallible human world he targeted in 1979, singing, “What good am I if I’m like all the rest?” He’s not only calling himself out; he’s calling himself a hypocrite. He goes on: “What good am I if I know and don’t do?” From a singer who’s known for his lyrics, often been hailed as a voice for the voiceless—and one who spoke with the assurance of revelation on songs like “Slow Train”—it’s a particularly cutting line. “What good am I while you softly weep,” he sings, conflating personal failure in a relationship with the large-scale failure of turning “a deaf ear to the thunderin’ sky.” This is a testament to one of Dylan’s greatest strengths: His ability to consistently reckon with his own myth. – Tyler Dunston

“Shooting Star”

Dylan has a particular song type based on this recipe: take some mythic or religious imagery, add just a dash of the personal and mix it together so that no one’s quite sure what it’s about. In the wrong hands, the formula leads to disaster, to a portentous mash-up of nothing. Dylan’s unusual skill with these images allows him to shape songs that express more than they delineate, replacing potential vagueness with evocative ambiguity. “Shooting Star” closes Oh Mercy with just that sort of work, establishing an almost-narrative and an almost-prayer while leaving any final understanding open-ended enough for the listener to glide into.

The song is rich with loss, with both departure and missed opportunity. The first verse seems to tell of a partner who disappeared while reaching for something bigger, “a world I never knew,” though the melancholy of the tune suggests more to the story. The second verse relies on self-reflection, as Dylan despairs while considering his own possible shortcomings. It’s the bridge that changes the tone, bringing in the explicitly religious imagery: the “fire truck from hell,” “the last temptation” and even “The Sermon on the Mount.” It ends with a radio playing, though, undercutting the spiritual tone. The fourth verse lets Dylan settle down. The end times haven’t come, either for him or for the world. If we suffer his losses with him (and reflect on our own), we also feel the chance (or the burden) to carry on.

All of which would be fine and fit the form, but Dylan develops a beautiful melody for his reflections, perfectly embraced by Lanois’ production. Aside from a couple moments in the bridge, the chord progression’s unsurprising, the sort of pattern Dylan would have found with little thought, but that allows a sort of ease in the song’s setting. Dylan’s not raging against brief chances or the dying of a shooting light; he doesn’t struggle to find meaning. He simply thinks of those people and moments that come to mind naturally during relaxed dolefulness. We can’t stay quite that calm, though, because the bridge with just a few unlikely chords and a heightened tension, does the heavy work of unsettling us, even if Dylan finds his way back to earth. – Justin Cober-Lake

“Dignity”

This is one of the more difficult Bob Dylan songs, at least according to its composer. Written during the Oh Mercy sessions, it was one that Dylan and Daniel Lanois apparently tinkered around with so much that everyone else who worked on it just gave up one day. It’s since been released in multiple versions, but the one included on Side Tracks–ironically, a version that Dylan and Lanois felt was unfinished–is easily the best version of the song.

While it never made it to Oh Mercy, it still fits in the overall mood: the production is muddy and hazy, a far cry from the plastic sheen of Empire Burlesque, and Dylan carries himself with more verve and purpose than he did through the rest of the decade. And, like the rest of Oh Mercy, “Dignity” possesses a quiet rage. Aside from possibly “Political World,” it’s Dylan’s most direct condemnation of the culture of crass, careless consumerism that was the ‘80s.

The word “dignity” stands for a lot in the song, but in the narrative that Dylan tells, “dignity” is conspicuous in its absence. It’s a resource in high demand and low supply, and it’s a long-forgotten concept that seems all too relevant now that people ignore it. The song doesn’t build so much as it maintains its pace, mirroring the quest of Dylan’s speaker for, essentially, a shred of human decency. By the end, though, the quest seems to be fruitless; the world is simply too cruel for dignity to exist. Dylan ends on a bit of a cynical note, wondering aloud, “What’s it gonna take/ To find dignity?” Crucially, though Dylan seems weary and beaten down, he doesn’t sound like he’s given up. He’s going to find dignity, even if he has to keep looking forever. – Kevin Korber

“Series of Dreams”

Should this even be Dylan’s ‘80s list? Our panel was split. Recorded in 1989 and then not used on Oh Mercy a remixed version of “Series of Dreams” appeared in 1991 on The Bootleg Series Volumes 1-3 (Rare and Unreleased), continuing a trend where Dylan left his best songs off his albums for some inexplicable reason.

Dylan must have thought “Series of Dreams” was good, however, including the song on the third volume of his greatest hits in 1994. Featuring Daniel Lanois’ adventurous production, the song caps off a turbulent decade for Dylan, sending him into the ‘90s on a strong note.

“Series of Dreams” grips the listen from the start with its rollicking and inviting sound, never letting up throughout. The song narrates a succession of nocturnal visions “Where nothing comes up to the top/ Everything stays down where its wounded.” Dylan tells us of feeling helpless in these dreams, perhaps a progenitor for the work he would later do on Time Out of Mind. Like any good dream, the images here are semi-coherent, semi-hallucinated, but like any good poet, Dylan does his due diligence to make some sort of sense out of it all.

“Dreams where the umbrella is folded/ Into the path you are hurled/ And the cards are no good that you’re holding/ Unless they’re from another world,” Dylan sings over the bridge, making the case that unless you play the cards you’re dealt in the corporeal world well, you may suffer the unending terror of the dream world. However, when the song ends, Dylan claims that he’s “gone the distance.” Could it be a summation on his three-decade career or his role as a poet where he faces up to doubt and uncertainty? Or could it be both?

Lanois and Dylan butted heads over the song. According to a passage in his book, Chronicles: Volume One, Dylan claimed the producer wanted the entire song to sound like the bridge. Lanois also wanted to begin Oh Mercy with “Series of Dreams.” Can you imagine what an opening at would have been? Instead, it was relegated to the vault. – David Harris