What does an artist who has already been inducted into the kitschy, boomer theme-park of the Rock & Roll Hall of Fame do when they’re only halfway through their career? In the 1990s Bob Dylan, like many artists of his generation, was faced with this question. But irrelevancy is not so much a judgement of quality as it is a matter of perception.

Part of what these lists have been doing is telling a story about Dylan’s career. From the constant reinvention of the ’60s, to the musical prime of the ’70s and up to the revelatory wilderness of the ’80s, that story has been told – if incompletely – by the songs we’ve chosen. But the ’90s are messier. This isn’t quite a “lost” period, though there were far fewer songs in total for us to choose from this decade. Despite this, there was only one song our contributors’ lists shared in common. Dylan, as ever, remains impossible to pin down.

While Under the Red Sky is often thought of as an inauspicious start to this decade, no less a critic than Robert Christgau praised it as the best thing Dylan had done since Blood on the Tracks. Returning to folk music for the first time in three decades, Dylan’s duo of stripped-down traditional albums would be his most successful experiment in self-production up to that point. One likes to imagine a solitary Dylan fan who had waited 30 years, keeping the faith that Judas would atone for his sins, finally being rewarded. Such a person probably did not exist, but it’s a profound experience hearing these songs Dylan once had to fake the maturity to understand delivered by a man who had at last earned that maturity. By decade’s end, Dylan’s atmospheric reunion with producer Daniel Lanois, Time Out of Mind, would prove to be his most widely acclaimed album, winning the big prize at the Grammys – the first and only time Dylan has done that.

But even in this mixed decade, Dylan still managed to pull off a revolution: The Bootleg Series. Forever changing how popular musicians catalogue their past, Dylan’s archives still stand above the many imitators that have come in his wake. We’ve talked around these releases themselves, including several Bootleg tracks throughout our series, but it’s impossible to imagine Dylan fandom – and especially this list below – without them. – Ian Maxton

“Born in Time”

“Born in Time” sounds particularly urgent on an album as tonally varied and hit-or-miss as Under the Red Sky. Then you remember it was, like “God Knows,” an outtake from the Oh Mercy sessions, which saw Dylan unafraid of sounding earnest or even sentimental. Sonically, though the song’s structure evokes Oh Mercy, the production is quite far from Lanois’ dark atmospherics—though it does share a kind of spaciness, a desert haze instead of a smoke-filled empty barroom.

This expansiveness resonates with Dylan’s lyrics, which are generous—still narratively obscure, but emotionally bare, yet the tone is often hard to place. The song’s ambiguities define it, like the wonderful wording of “in Time” in the title, which both evokes being ‘on time,’ as in not too late, and being ‘in time,’ as in, not out of time—which is, perhaps, to say, this is not an out-of-this-world love but a grounded, embodied love. Does this lived-in realism make it less transcendent? On the contrary, the romanticism of the “blinking stardust of a pale blue light” isn’t undercut by the realization that “truer words/ Have not been spoken” needs the addendum of “or broken”—instead, it is amplified by it.

That “Born in Time” sounds vaguely out of time, like a classic songwriter’s song that could have been written in a number of decades, and yet specific—it sounds very much like a particular version of Dylan, one with the ’80s behind him—is not a contradiction either. On “Born in Time,” as with many of Dylan’s greatest songs, his romanticism and his realism intersect. -Tyler Dunston

“2 x 2”

Dylan began the decade and Under the Red Sky with one of his silliest songs, “Wiggle Wiggle,” but, even though it may have been meant to entertain his then-four-year old daughter, an early version included suggestions of the apocalypse. So this equally simple-seeming song, which comes off like Dylan doing “Schoolhouse Rock,” is almost as frequently dismissed. But much as fairy tales often hide sinister elements, Dylan here addresses much more than integers. The most immediate resonance is with Noah’s Ark, which Dylan directly references in the final verse, but it’s the middle section that breaks out into the kind of bluesman mysticism that can make a song that appears so casually tossed off into something as fatalistic as Robert Johnson. “How much poison did they inhale?/ How many black cats crossed their trail?

Dylan’s special guests on this one include David Crosby, Elton John (who gets a keyboard solo) and Brazilian percussionist Paulinho da Costa, and the all-star lineup on a track that sounds nothing like an all-star showcase reinforces the sense of Dylan’s fatigue with the whole business of music. “How many tomorrows have are they given away?/ How many compared to yesterday?/ How many more without any reward?/ How many more can they afford?” In the guise of teaching multiplication tables to his kid, he’s issuing a bitter rebuke that’s as pointed a piece of evangelism as anything from his more explicitly Christian era. Even the arrangement seems to invoke the elders; David Lindley opening this off with the bouzouki, which resembles lute-like instruments that go back to ancient Greece. “2 x 2” is more evocative than its simple construction might indicate, and the fact that its performed by a group of seasoned hit-makers somehow makes it that much stranger. — Pat Padua

“God Knows”

After hearing Lanois’ evocative production, Dylan fans may found it a backwards move to go with the Was brothers’ slicker sound on Under the Red Sky. But there were drawbacks to the Lanois stamp; as Clinton Heylin wrote, there was an Oh Mercy outtake that Dylan hadn’t given “enough identity to lift it out of Lanois’ swampy soundscape.” Indeed, by the end of the ‘90s Lanois would further overwhelm Dylan’s songcraft –is “Love Sick,” as great as it is, more about the producer than the artist? Yet here the more straightforward production got closer to Dylan’s essence, and the outtake on Tell Tale Sings reveals that this second round got it right.

Stevie Ray Vaughan playing lead doesn’t hurt. The bluesy shuffle sounds laid-back enough that it could have been an impromptu jam, but sometimes simplicity is arrived at after some deliberation. “God knows it’s fragile,” and “terrifying,” and this heavenly omniscience is delivered over music that sounds of a piece with his great ‘60s electric records. It’s if the voice of his generation , after years of flailing and a stint with Christianity, had finally synthesized the grizzled bluesman influences of his early years with his mid-career evangelical impulses. The result was something familiar, yet not: this is the blues alright, but instead of the fatalistic doom of a blues progression inevitably leading the singer down below, Jimmie Vaughan’s basic riff—and especially David Lindley’s slide fills climb pout of the depths, elevating mere studio professionalisms into a surprisingly effective religious metaphor, all in the format of a three-minute rock song. The message, bridging a broad expanse of Dylan’s career, doesn’t end with the fade-out either; “Handy Dandy” quickly follows with an organ line (played by Al Kooper himself) that’s a throwback to “Like a Rolling Stone” and a deceptively childlike title that leads to references from Shakespeare. – Pat Padua

“Jim Jones”

When it was released in 1992, Good As I Been to You was perceived as something of a surprise, an album of folk covers and traditional songs, played almost exclusively with just guitar and vocals, resulting in a conceptual release more akin to the work Dylan was doing in the early-‘60s. After a decade spent wandering the pop wilderness with a handful of somewhat baffling releases, Good As I Been to You could easily have been seen as a cleaning of the slate, a return to an earlier time or a re-grounding in his roots as a folk musician. And while it didn’t really turn out to be any of those things, it nonetheless offered up an appreciative reminder of why Dylan was so revered in the first place, having taken existing songs within the folk canon and made them his own (alongside his own compositions that would obviously be joining – if not outright rewriting – the folk canon from the mid-20th century on).

One of the more obscure songs on the album, “Jim Jones” is 19th Century Australian folk ballad commonly referred to as “Jim Jones at Botany Bay,” detailing the literal trials and tribulations of the titular character. After having been found guilty of poaching, Jones is sentenced to a stay in Botany Bay. Along the way, however, the ship on which he was traveling was attacked by pirates – a fate Jones much preferred to the idea of Botany Bay – only to have them driven away, Jones’ destination remaining unchanged. Finding himself in chains, Jones vows to escape into the Australian bush and exact his revenge on those who sent him to this cursed land. The story ends without resolution, but during the song’s rather brief runtime, Jones becomes a fully-fleshed out character along the lines of some of his best, the song effectively becoming Dylan’s own through his gravely, nasal read of the nearly 200-year-old song. – John Paul

“Froggie Went A-Courtin’”

When Dylan says he’s recording traditional songs, he means it. “Froggie Went A-Courtin’” dates all the way back to 1548, a version of which probably first appeared in Scots in the Complaynt of Scotland, a work that appeared during the war of the “Rough Wooing” against England. Despite its playful descriptions of Frog’s marriage to Miss Mouse, the arrival of an array of wedding guests—an old gray cat, a bumbley bee and a hungry snake—and Mr. Frog’s eventual demise when a “lily-white duck” comes and swallows him up, there may have been potential political/allegorical resonances to the work which remain difficult to parse.

The somewhat baffling decision to close the album with this rendition speaks to Dylan’s penchant for subverting expectations, a testament to the fact that, even when we’re dealing with covers, Dylan’s personality, sense of humor, and organizing hand is all over Good as I Been to You (keep this in mind for when we turn to Dylan’s turn to the “Great American Songbook” in the 2010s).

Dylan’s choice to end on “If you want anymore, you can sing it yourself, uh-huh,” calls attention to the endless variety of the song’s form (compare to Woody Guthrie’s version, in which he ends on, “A snake, and a frog, and a Miss Mousey, hey hey hey hey”). It feels appropriate for an album which is filled with longing for something unattainable, the longing to tap into the infinite—in “Jim Jones,” the speaker sings mournfully, “I’d rather have joined that pirate ship/ Than gone to Botany Bay,” and “Canadee-I-O” centers on the longing to see the titular far-off place. The reference to a kind of endless iterability of an old song with variable verses like “Froggie Went A-Courtin’,” is, appropriately, a structural one, and in the closing lines, Dylan makes a kind of joke about it. The tone is classic Dylan—wistful longing one moment, wry humor the next. – Tyler Dunston

“You Belong to Me”

Bob Dylan has long been notorious for leaving his best material off his releases. Just look at some of the deep cuts from his ‘80s material for proof that the musician isn’t always forthcoming with prime work. The same could be said for his 1992 covers album, Good as I Been to You, where Dylan didn’t include one of his best recordings of the decade, a take on ‘50s romantic ballad “You Belong to Me.”

Written in 1952 by the team of Chilton Price, Pee Wee King and Redd Stewart, the oft-covered tune lends itself perfectly to Dylan’s grizzled voice. Initially written by Price as a paean involving lovers separated by World War II, King and Stewart gained credit for popularizing the tune and tweaking the lyrics to make the separation less specific and more universal in its appeal. It became a mainstay for ‘50s singers, both male and female, to interpret.

Accompanied only by an acoustic guitar, Dylan’s mood is definitely plaintive, a wistful take on a song about longing and loss. While Dylan’s missing lover visits the pyramids of Egypt, wanders a market in Algiers, traverses the world in a silver plane, he mourns: “You belong to me/ And I’ll be so alone without you/ Maybe you’ll be lonesome too.” He’ll be waiting for this wayward lover to return, if she ever does.

This track ultimately turned up on the Natural Born Killers soundtrack, a moment of quiet among noisier counterparts such as Nine Inch Nails, Dr. Dre and L7. Though marred by the inclusion of dialogue between Woody Harrelson and Juliette Lewis, a version without their voices exists on YouTube but it’s truncated. Either way, this song is ripe for a Bootleg Series inclusion, it’s sadness timeless, always ready for a revisit. – David Harris

“Miss the Mississippi”

Dylan’s career began by covering the songs of other artists, and every time he has needed a new beginning, he has returned to these songs – the ones that American music is made of. Recorded with David Bromberg – a contributor to a previous Dylan new beginning, Self Portrait – as part of an album session that was ultimately discarded in favor of Good as I Been to You, “Miss the Mississippi” is a song originally recorded by Jimmie Rogers in 1932.

The word here is simplicity. Opening with a duet between Dylan’s guitar and harmonica before the band arrives to gently bolster his voice with brushstroke drums, minimalist electric guitar and bass and a mandolin gently plucked in tremolo, the lyrics evince homesickness – longing for youthful days spent aside the titular waters. Dylan’s voice has always sounded older than he is, and just over 50 at the time of this recording, he sounds ancient. But the song isn’t overly somber. There’s a wistful tunefulness to Dylan’s delivery that accentuates the soft-touch of the instrumentation.

In the final verse, what sounds like a clarinet and a horn join the rest of the band to complete the early-century charm. While the sound of the track presages Dylan’s work in the 21st century, you can almost see Dylan in a candy-striped suit, crooning from some grand white gazeebo in an idyllic pre-WWI town square, and for a moment you forget the melancholy of the lyrics. But then the darkness creeps in again, that darkness that lies heavy under the thin American veneer.

This is what the best American songs do, and it’s clear why Dylan was drawn back to this music that pre-dated him. Robert Zimmerman might have been born in 1941, but Bob Dylan came from someplace older. – Ian Maxton

“Blood in My Eyes”

On the surface, “Blood in My Eyes” is a song about one thing: a man haggling with a prostitute over the price of her services. Indeed, had Dylan recorded this song in the ’60s or ’70s, there would probably be more of a sense of levity in his rendition of the Mississippi Sheiks standard. However, Dylan chose to visit this song as part of his twin dour albums of folk and blues standards, with “Eyes” appearing on the superior of the two, World Gone Wrong. The Dylan who performed this song was older, one who no longer had to put on airs about seeing and experiencing the travails of the world because he had, in fact, experienced them. In this mode, he takes a silly song about haggling with a hooker and turns into something downright tragic.

Dylan plays the song at a slow, morose tempo in a spare arrangement that serves to underscore its inherent sadness. Rather than mock his narrator, Dylan appears to sympathize with him, to try to understand the intense sadness and isolation that would drive a man to pay for companionship. In Dylan’s hands, the speaker of the song becomes an object of some sympathy, rather than one of mere pity. He doesn’t ask for anything from the woman of his desire, as his repeated exhortation – “I don’t care what in the world you do” – would imply. He’s not just after sex, or even love; he wants companionship and human contact that the world has, for quite some time, deprived of him. – Kevin Korber

“Delia”

Ever since he was a young singer-songwriter, Dylan affected the gravelly vocals of a veteran bluesman. By the ‘90s, the scraggly veteran had the kind of time-worn voice, the sound of the Old Weird American, that he’d always wanted. So it makes sense that he’d use that seasoned timbre to revisit the folk and blues canon, which he started to tackle on Good as I Been to You and continued to face with perhaps increased intensity on World Gone Wrong. The traditional “Delia” is one of three murder ballads on the album, and if Dylan had begun the decade surrounded by celebrity guest musicians, here he’s gone back to his roots, just him and his guitar.

The “gambling girl” is based on a murder in Savannah, Georgia in 1900, when 14-year-old African-American girl Delia Green was murdered by her boyfriend Moses Houston. The incident inspired musicians from Blind Willie McTell to one-time Dylan collaborator Johnny Cash. While Cash sang “Delia’s Gone” from the point of view of the killer, Dylan is more removed from the scene; he knew her and loved her in vain: “..how can it be?/ You wanted all them rounders, never had time for me/ All the friends I ever had are gone.” Dylan at this late stage in his career was earning enough royalties from his ‘60s staples alone to make him a rich man several times over, but still he convincingly takes on the persona of someone history left behind, ignored by the woman he loved and forgotten by time. Is art an exercise in futility? Does a girl have to be murdered to be remembered? While Dylan is often celebrated as a protest artist speaking to the times, he’s at his most profound when he summons up images out of time, songs that weren’t his but that he made his own, reminding us of the tragedy and wisdom of the past. — Pat Padua

“Love Sick”

Dylan returned in a proper sense when Time out of Mind opened with “Love Sick,” a dark, spacious cut with plenty of patience. Even 20 years later, it feels like an odd single, with its tired pun of a title and its idiosyncracy delving into soft sounds and odd vocal cadences. It makes perfect sense as the start of one of Dylan’s somewhat regularly occurring comeback albums, one that launched a new era for the artist. It is defined by hits production (though Dylan would take over for Daniel Lanois after this one) and its use of an ahistorical past (Dylan wrote as if the 19th century and the 1990s happened simultaneously).

It takes just a few chords for the setting to be fully realized. Dylan’s bleakness immediately fills the room, and he’ll spend the whole track (and most of the album) trying to, if not understand it, at least become resigned to it. “I’m walking through streets that are dead,” he sings, but of course it’s not streets that can die. Dylan’s singer might be better off dead; he finds a particularly virulent form of alienation surrounding him as he slinks through a breakup. He blames his ex, he projects his feelings onto inanimate objects, and he forces anhedonia upon himself as he watches the world. The song grows darker with every listen.

He only wishes it were a feint. Dylan stumbles out of the song with his heartbreak made explicit, and we catch just a hint of the album’s animating spirit. This Dylan might be weary, but he turns it to experience and exploration. In “Love Sick,” he’s absolutely done with everything and doesn’t know how to go on, but he’s going to face it simply by exposing it. The deep despair – the crumbling both inside and out – persists, but Dylan, rather than hanging himself, hangs on (and finds that hanging on to shadows might make everything feel worse). For an album about everything growing dim, Dylan seems to start at midnight, somehow suspect that the worst is yet to come and keeps singing, shedding a little light on the darkness. – Justin Cober-Lake

“Standing in the Doorway”

Nine years ago, Matt Berninger of the National included “Standing in the Doorway” on a list of his 12 favorite “tearjerkers,” alongside the likes of Leonard Cohen, Tom Waits and Cat Power (as well as, um, Liars). “I don’t know how much of this song is autobiographical—I’m sure [Dylan] would say none,” Berninger says. “But it’s impossible not to think there’s a lot of honest truth in there.”

For a moment, suspend whatever disbelief you have about seeing the words “Dylan” and “tearjerker” in such close proximity. Dylan has written many songs about love, and almost all of them are soured by jealousy and vindictiveness. He’s written very few out-and-out love songs, and fewer still that you could call “tearjerkers.” “Standing in the Doorway” isn’t without its moments of bitterness, such as Dylan’s admission that he doesn’t “know if I saw you if I would kiss you or kill you.” But it is undoubtedly a love song, an eight-minute elegy for a love faded but not forgotten. And, yeah, it just might jerk a few tears out of you, too.

“Standing in the Doorway” isn’t just a highlight on Time Out of Mind, but one of the most underrated tracks in Dylan’s canon – although it would’ve still been pretty great in its original form, “Dreamin’ of You” (which also appears on this list). Despite having a few lyrics in common, the two songs feel like distinct entities. “Standing in the Doorway” is softer, even plaintive, and Dylan’s confession that “Last night I danced with a stranger/ But she just reminded me you were the one” just might be one of the most heartbreaking things he’s ever sung. Still, it’s Daniel Lanois’ hazy production that really transforms the song from a humid fever dream into a wistful memory, dissolving organ and pedal steel guitar in reverb and smearing them over the track like Vaseline on a camera lens; it puts you right there in Dylan’s blues, watching him stand in the doorway, crying, as the church bells ring for someone else. No wonder Dylan has self-produced all of his albums since – Lanois came as close as anyone could come to catching a glimpse of the man at the center of the myth. – Jacob Nierenberg

“Million Miles”

“Million Miles” doesn’t get the most attention of the Time out of Mind tracks, and it makes at least some sense. Dylan performs the song with a traditional blues structure, but the syncopated organ part gives it a little more bounce than most of the album’s tracks. It doesn’t conform to the dusky despair that Dylan perfected during this phase of his career, and on background listen, it lacks the stunning qualities you might look for in a classic. That reading misses the point a little, though.

It is the blues. On such a down album, it makes sense to include one just classic blues number, and Dylan does it superbly. The song takes a simple build but locks down the groove, allowing the band to build a fuller sound around. Dylan fully commits to his vocal, and his performance allows us to slowly discover the unreliability of the narrator. Of course, the truth (or lackthereof) to the singer comes in jus the third line of the song. Dylan sings, “You told yourself a lie – that’s all right mama I told myself one, too.” He sneaks in a reference to Elvis here, the first tip that the singer’s at play (and a few more allusions crop up). He’s not entirely what he seems.

But the reason he dissembles is that he’s genuinely hurt. He plays at being the victim (he probably isn’t), and he plays at being some sort of performer (covering for the fact that he actually is some sort of one), but in it all he reveals his misery. The distance between him and his beloved (or maybe his objective) tantalizes him. The only way through his dismay – as Dylan well knows – is to sing the blues. He covers his pain by being playful, suggestive and even funny, but the pain of those million miles still comes through. – Justin Cober-Lake

“Tryin’ to Get to Heaven”

Producer Daniel Lanois is often associated with swamp. That murky feeling on Dylan’s 1997 “comeback album,” Time Out of Mind, is credited to the Canadian producer/musician, a touch that Lanois also applied to icon Neil Young’s Le Noise. Dylan finds himself in the swamp, literally, in the opening lines to “Tryin’ to Get to Heaven,” just one of the many triumphs he packed onto Time out of Mind.

The air is getting hotter/ There’s a rumbling in the skies/ I’ve been wading through the high muddy water/ With the heat rising in my eyes,” sings Dylan, kicking off the quixotic song that finds the singer in locales along the Mississippi River, wending his way down to New Orleans. Could he be traveling the mythic Highway 61 of his youth? If so, the destination is a very different place this time.

In the song, Dylan addresses someone or something from the past. Could it be an old lover or even his younger self as he traverses the country south? Either way, this wraith is losing its hold over our narrator, its memory growing dimmer. So where is Dylan heading in this lonely landscape with his broken heart? Well, heaven. But he needs to hurry because the door is about to close.

More than anything, “Tryin’ to Get to Heaven” sounds like an aging songwriter taking stock, reliving glories of travel and sexual conquests before he skips off this mortal coil. Dylan sings of “reliving his dreams” to check that everything is “as hollow as it seems.” These are exhausted words and none more so than a lyric that appears on the singer’s website but didn’t make it into the song: “When you think you’ve lost everything/ You find out you can always lose a little more.” The discrepancy is telling. Time Out of Mind is often billed as one of Dylan’s bleakest albums. Why did he retreat from the lyrical void at the end? To save himself a spot in heaven? – David Harris

“Not Dark Yet”

Time Out of Mind is generally regarded as Dylan’s finest collection of songs since Blood on the Tracks. That’s probably true. But as our lists of his (post-Blood) ’70s, ’80s and now ’90s tracks have shown, he never stopped releasing an embarrassment of good-to-great material. Regarding Time Out of Mind in particular, many consider “Not Dark Yet” its crowning achievement. Perhaps that’s also true. Still, the album contains ten other viable contenders, depending on which version of Dylan you prefer.

The song’s languid, fatalistic beauty no doubt makes it his most beguiling composition since “Blind Willie McTell.” Regret saturates every raspy couplet. Cynicism pervades this reflexive evaluation of a life lived. The Reaper’s a knock, knock, knockin’ on his front door. “It’s not dark yet,” Dylan intones over and over again in a none too subtle allusion to his namesake, “but it’s getting there.” This kind of midlife lamentation normally results with the purchase of a shiny new sports car. Dylan instead decided to record a woeful dirge: “Sometimes my burden/ Is more than I can bear,” he sighs halfway through the song.

Despite all this despair, or probably because of it, “Not Dark Yet” offers succor, something like homeopathic medicine. There’s a reason many of us rushed to revisit Soderbergh’s Contagion when a real-life pandemic broke out earlier this year. That impulse goes straight back to Ancient Greece, to the birth of tragedy – catharsis. On “Not Dark Yet”, Dylan is at once our Aeschylus and Agamemnon, the tragedian and tragic hero. Bad shit may be timeless, but reality can, by contrast, be a little bit better than fiction. Cold comfort. And comforting, nonetheless. – Peter Tabakis

“Cold Irons Bound”

With Dylan, it feels like we spend most of our time talking about his lyrics, and with good reason: he’s the closest that the rock era has ever come to producing an actual poet. But when talking about Dylan’s ’90s work, it’s impossible to talk about how Dylan’s sound substantially changed in a way that didn’t have much to do with his lyrics. “Cold Irons Bound” is the ur-example of what Daniel Lanois could do with Dylan, a collaboration that started back with Oh Mercy but arrived in full form on Time Out of Mind. In contrast to the clear, compressed sounds that Dylan began the decade with, “Irons” is incredibly murky, an echo-laden blues jam that sounds completely disassociated from this plane of existence. Dylan’s voice, by this point weaker and thornier than it had been at his peak, could have been lost in the studio ether, but it instead sounds haunted, a spectral song from a realm beyond ours.

These ghostly aspects of the song play very well with Dylan’s mood at the time. Having recovered from a near-death experience around the time of the album’s composition, Dylan appears to be singing to the oncoming light at the end of the tunnel on “Cold Irons Bound.” Dylan opens by implying that he himself is a spectre (“I’m waist deep, waist deep in the mist/ It’s almost like, almost like I don’t exist/ I’m twenty miles out of town in cold irons bound”). From there, he recalls a past life with lovers abandoned and old grudges still held. Each couplet is delivered in Dylan’s disengaged manner as he plays the part of a being above it all. Having brushed close to death, the petty squabbles he once took part in seem trivial in retrospect. – Kevin Korber

“Make You Feel My Love”

What’s most striking about Dylan’s version of “Make You Feel My Love” is how unassuming it is. Coming near the end of his 1997 “comeback” album, the critically-lauded Time Out of Mind, it doesn’t, in its original context, strike the listener as all that remarkable. Accompanied by a lone piano, ghostlike bass line and slightly woozy sounding organ playing sustained notes throughout, the arrangement of the song isn’t terribly remarkable, the meat of the song itself relying on Dylan’s surprisingly emotional read and jazz-like chord progression. Other than that, It’s little more than a pleasant enough love song along the lines of some of Dylan’s least cryptic, most accessible bits of pop-leaning songwriting. There’s nothing immediately grabbing the listener and declaring, “This song is going to become a modern-day standard the likes of which few contemporary writers could ever hope to achieve!”

And yet it has in the last several decades, done exactly that. It has now been covered by more than 450 artists, including: Adele, who had a hit with the song when it was released as the fourth single off her 2008 debut, 19; Garth Brooks, who took the song to number one on the Billboard Country charts in 1998; and, the year prior, Billy Joel, who managed to take the song halfway up the Billboard Hot 100 when the song was released as the lead single off his Greatest Hits Volume III. Indeed, most would probably be quite surprised to find out that the heavily adult contemporary-leaning ballad was penned by Dylan, making it not just all the more remarkable in and of itself, but a greater indicator of just how unbelievably gifted a writer Dylan has remained over the years.

Indeed, “Make You Feel My Love” could easily be considered part of the canon known as the Great American Songbook, something he has spent much of the 21st century exploring himself, perhaps getting a better feel for the rarefied territory within which his writing unimpeachably now exists. – John Paul

“Highlands”

Bob Dylan has a penchant for ending his best albums with ambitious tracks whose runtimes splay beyond a typical three to five minutes and sometimes unfold well into the double digits. His most ambitious outliers (“Desolation Row,” “Sad Eyed Lady of the Lowlands” and, most recently, “Murder Most Foul”) tend to be highlights, not only because Dylan’s prowess can easily handle such bravura sonic and narrative marathons. They offer him a unique role in the modern pop-cultural landscape, one of an Olde Tyme troubadour, part of an oral tradition in the lineage of ancient and medieval poets.

“Highlands”, which concludes Time Out of Mind, stretches across 16-plus minutes in no hurry to go beyond its title location, some thoroughly mundane place a world away from the depravity and excitement of Desolation Row. After experiencing the wonders of nature (“Honeysuckle blooming in the Wildwood air/ Bluebells blazing where the Aberdeen waters flow”), he wanders into a Boston diner and across multiple verses counters a waitress, his foil, who disputes the very nature of Dylan’s genius and whether or not he’s a feminist.

Once the narrator flees the restaurant without a proper rejoinder (despite claiming to have read Erica Jong), the song turns almost pastoral with “the horses and hounds” who are “way up in the border country, far from the towns.” Dylan rambles over hills and through hamlets (“I see people in the park forgetting their troubles and woes/ They’re drinking and dancing, wearing bright-colored clothes”). Signs of life and survival pervade, but Dylan knows better. A random interlocutor asks if he’s registered to vote and he pirouettes with a non-answer: the sun, after all, is still shining (“but it’s not like the sun that used to be”). We’re suddenly in 2016 (“The party’s over and there’s less and less to say”). Dylan ends the song on a note of hope. He’s “over the hills and far away,” at least in his mind, something we can all relate to nowadays. – Peter Tabakis

“Dreamin’ of You”

Recorded during 1997’s Time Out of Mind but not released until 2008’s The Bootleg Series Vol. 8 – Tell Tale Signs: Rare and Unreleased 1989-2006, “Dreamin’ of You” sounds of a piece with the material alongside which it was recorded. Relying on a darker, rawer sound than anything he’d recorded in the prior decade, the music recorded for and around Time Out of Mind truly saw Dylan coming back into his own, as if once more engaged in the idea of being a writer and musician of some consequence. Because of this, “Dreamin’ of You” is a knotty bit of poetic abstraction and dreamlike imagery that helps evoke the sensation of dreaming.

In order to evoke the often surreal feel of a dream, the song’s instrumental arrangement is all woozy, wobbly performances that help perfectly underscore and enhance the dreamlike imagery. “The light in this place is really bad/ Like being in the bottom of a stream,” he sings, perfectly encapsulating the hazy nature of dreams as they are experienced a vaguely recalled upon waking. Here as elsewhere during this time period, Dylan receives a massive creative bump from producer Daniel Lanois who managed to harness Dylan’s lyrical aesthetic and give it a musical accompaniment it hadn’t had in ages.

That the song’s eventual release was accompanied by the dusty, dreamlike Harry Dean Stanton-starring video in which Stanton-as-private investigator attempts to makes sense of the Dylan mythos via bootleg recordings and grainy concert footage, while haunted by the man himself (or something along those lines?) make the lyrics land all the more solidly. It’s another fine example of Dylan finding his feet once more and following his idiosyncratic muse further on down the road, aided and abetted by like-minded co-conspirators who, together, manage to operate at the top of their respective games. – John Paul

“Red River Shore”

One of the great strengths of Dylan’s songwriting is his ability to create music that sounds primordial, like he drew it from the well of the past and is merely serving as the vessel delivering it into the present. “Red River Shore” is such a song. It’s something of a sequel to the cowboy song “Red River Valley” – even alluding to the chorus of that tune when Dylan sings, “Well I sat by her side and for a while I tried/ To make that girl my wife.”

“Red River Shore,” like that older song, is about lost love. For the first half, it proceeds in the expected vein of longing, and does that thing folk songs do where they repeat a cliché and make it new by injecting it with true feeling. But around the fifth verse, the song shifts as Dylan sings, “Well we’re livin’ in the shadows of a fading past/ Trapped in the fires of time.” His memory turns to doubt and uncertainty. He is a “stranger in a strange land” where “nothing looks familiar,” even though he is certain he’s been to these places before with the girl he once loved.

Spurred by this doubt, Dylan seeks out the people that should remember the time he and the woman spent together, but no one knows her. The penultimate verse ends with a vision of the world in permanent darkness. This defamiliarization of the folk song is made even stranger by the final verse, where Dylan muses on the possibility of raising the dead, of eternal recurrence and of his own ghostly state.

Recorded during the Time Out of Mind sessions, Dylan didn’t feel the production or arrangement was right, so the song stayed off the album. It’s hard to disagree with him. As the lyrics grow stranger, the instrumentation loses its way, stacking on more elements to diminishing returns. While a great producer, Dylan’s relationship with Lanois could be contentious – their visions sometimes didn’t match up – and Dylan abandoned more than a few gems because prolonging time in the studio didn’t hold much interest for him. Still, even in imperfect form, “Red River Shore” is a strong example of why The Bootleg Series is so valuable as a showcase of Dylan’s poetry and process. – Ian Maxton

“Things Have Changed”

If you remember one thing about the 2000 film Wonder Boys, it’s that it has Michael Douglas in it; if you remember two things, it’s that Dylan wrote one of his best songs of the last 30 years for it. Having Dylan pen a new tune for the movie was a fitting choice—after all, who would know better than Bob Dylan the enormous pressure of being a (ahem) boy wonder, of achieving greatness at a young age and having to continually live up to past glories? Sure enough, “Things Have Changed” packages familiar themes—love gone wrong, the inevitability of time, Judgment Day—in a bluesy stomp that begins with Dylan receiving a lap dance from an assassin-eyed woman and peaks with him hauling another off in a wheelbarrow. Is this the same Dylan who sounded like a total doofus on “Wiggle Wiggle” just a decade earlier? Because this grown-ass man sounds like the coolest cat on the block.

It’s also fitting that “Things Have Changed” is the final song on our list of Dylan’s best songs of the ‘90s, seeing as it marked not just a clean break from the atmospheric gloom of Time Out of Mind, but it effectively crystallized Dylan’s current (and possibly final) persona: a grizzled, seen-it-all bluesman who keeps looking over his shoulder for the hellhound on his trail. It’s a thread that’s run through his best work of the last two decades, as recently as this year’s disarmingly earnest Rough and Rowdy Ways. But even more pointedly, it feels like a rejoinder to the young folksinger who wrote “The Times They Are A-Changin’,” who sang so passionately about overcoming political and social injustice. “Things Have Changed” isn’t a protest song—it’s a jeremiad, a bitter admission that some things never change. – Jacob Nierenberg

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