It’s hard to overestimate how much Time Out of Mind, Bob Dylan’s 1997 masterwork, revitalized the aging artist. The winner of an Album of the Year Grammy, it heralded the most enduring “comeback” in a career filled with them, an inflection point after nearly 20 years of truly unfair) cultural irrelevance (if not outright dismissal and scorn from friends and foes alike). The overwhelming goodwill that record inspired carried over and even crested in the ‘00s.

That Dylan produced such superb new music in his fifth decade as a recording artist is an unprecedented feat none of his peers – the living giants of the ‘60s and ‘70s – have matched. And he did so with remarkable consistency. “Love and Theft” (2001) and Modern Times (2006) rank among his finest albums. Plumbing the depths of folk, blues, honky-tonk, the American Songbook – and their synthesis, rock and roll – those twin albums brim with vitality and pathos, largely thanks to his band of studio pros who had been around for the long ride of a Never Ending Tour. Their symbiosis is complete and on full display. Dylan finally became the song and dance man he always claimed to be.

Together Through Life (2009) is unquestionably second-tier, but only by comparison. Its accordion-drenched sound (thanks to David Hidalgo of Los Lobos) is reminiscent of Desire, and Scarlett Rivera’s pervasive electric-violin countermelodies and flourishes. Together is merely very good, as is its follow-up, the unlikely collection of holiday standards, Christmas in the Heart (2009). And then there’s the vault-opening of Dylan’s ongoing Bootleg Series, whose four volumes released in the ‘00s featured two classic live performances (the best being the raucous Dylan Live 1975, The Rolling Thunder Revue) and the fascinating alternate takes that spanned his entire catalog on No Direction Home (2005) and Tell Tale Signs (2008).

During the ‘00s, Dylan proved an artist can have not just one (the ‘60s) or two (the ‘70s), but three distinct Imperial phases. And if this year’s Rough and Rowdy Ways points to where he’s going in the 2020s, we may just be at the start of a fourth. – Peter Tabakis

“Tweedle Dee & Tweedle Dum”

Kicking off his first album of the decade, this quickly suggested that Dylan’s late ’90s comeback would continue at full speed. The band’s energy charges the sounds of traditional American music; Dylan hasn’t sounded like he’s been having this much fun in ages. If one version of Dylan grew up into The Basement Tapes, this version grew out of it. The band – including the always effective collaborators Larry Campbell and Charlie Sexton – have come to party. The track rollicks, with the guitars providing perfect fills as everyone powers the train. With its blend of folk and blues and hints of rock, the sound exemplifies the best of late-era Dylan, creating a celebration without hiding the dark spots.

Dylan mixes lyrical allusions just like he combines folk sounds. The title characters might be biblical, they might be cartoons or they might be violent vagabonds. They might be more than two people. The song never produces a narrative, but it delivers a sort of travelogue of imaginative meanings to sketch together a sequences of experiences only gestured at. The duo – lifted from Lewis Carroll as the first of many loving thefts in the album – begin in Nod, a location that, along with the knives and corpses, puts a murderous edge on the tune. Dylan’s allusions suggest their wandering leads them through the mythic American South. Briefly, we think they might find a harmonious way to settle down, but an inherent flaw in the pair leads to inevitable conflict and a return to the violence of the opening stanza. The threat of fratricide never sounded so much fun, as Dylan winks and (yes) nods through the whole run, with his band ready to match his drive. – Justin Cober-Lake

“Mississippi”

It’s been pored over, picked apart, researched into and argued about since its official release on “Love and Theft”. Some insist it’s simply the lovesick tale of a wayward wanderer. Others suggest a more political reading, one that stretches back to the moral blight of American slavery and the fundamental contradictions of our Founding Documents.

In typical fashion, Dylan himself has been of little help, though he’s hinted at the latter interpretation. But dilettantes and academics alike agree on one indisputable fact: “Mississippi” ranks high as one of Dylan’s most complex, melodic and stunning compositions in a career brimming with them.

During its five-plus-minutes runtime, it swings wildly between existential despair and spiritual enlightenment. “Your days are numbered, so are mine,” he growls at the start. Humankind is “all boxed in,” “trapped” with “nowhere to escape.” The “sky is full of fire, pain pourin’ down,” a lyric that eerily anticipates the album’s ill-timed release date on September 11, 2001. Three-quarters of the way through this otherwise jaunty number, Dylan is fully “drowning in the poison” with “no future” and “no past.

Then, the big pivot. Despite all the apocalyptic woe, his “heart is not weary, it’s light and it’s free.” He’s arrived at a Zen-like state of acceptance: “I’ve got nothin’ but affection for all those who’ve sailed with me.” So sings the author of “Positively 4th Street,” “Like a Rolling Stone” and “Idiot Wind,” three of the most scathing takedowns in popular music history. By the time we get to a final mea culpa (for a transgression we never really understand), Dylan implores his lover (or is it the listener?) to “stick with me baby, stick with me anyhow.

“Mississippi” looks to the future in its final moments. “Things,” Dylan speculates, “should start to get interesting right about now.” True. Two endless wars, the Great Recession, America’s first Black president, the legalization of same-sex marriage, Donald Trump and a global pandemic eventually followed. A mixed bag of history. But “fortune is waitin’ to be kind.” And so, we still wait, impatiently. – Peter Tabakis

“Summer Days”

It’s both unfortunate and kind of inevitable that Dylan doesn’t get much credit for having a sense of humor. His work is so steeped in the mythos of him being the Greatest American Songwriter that it’s easy to forget that he’s a human being, and like all human beings, he sometimes just wants to kick back and enjoy himself. “Summer Days” is one of the most genuinely fun songs on an album that has more than its fair share, but Dylan ends up being far too clever of a writer to have simple, brainless fun. In essence, this is his reflection on getting older and the changing times he’s lived through, but where some songwriters would turn such a concept into a somber acoustic dirge, Dylan and his band cut loose on a 12-bar blues with swinging drums and jazz guitar inflections.

However, while Dylan may be reflecting on his past, he does so with a wink and a nod to the audience. The narrator isn’t necessarily Dylan himself, but a character that stands in both for his real experiences and his odd fantasies. Here, Dylan is throwing money around, chatting up girls who don’t seem all that interested, and toasting Elvis. Eventually, the song winds through this speaker’s life, through an ill-advised marriage and towards a confrontation with his maker. Yet even as the lyrics take a turn, Dylan’s effortless vocals and the band’s breezy performance keeps things light and easy. The lyrics have a cyclical nature, ending where they began as Dylan seems to imply that life will keep going beyond him (or this Court Jester version of him), and the band’s looping patterns echo that sentiment. Never has an acknowledgement of the fleeting nature of existence sounded so fun. – Kevin Korber

“Floater (Too Much to Ask)”

One of the early revelations one has if one studies Shakespeare at all is that he was an inveterate thief. His plays were almost always assemblages of other sources – sometimes folk tales or myths, and sometimes other plays as well. Originality is a tricky concept; there may well be nothing new under the sun in art. Most would agree that influence is unavoidable, but at what point does homage become plagiarism? Bob Dylan, having imbibed continually the spirit of folk music even as his sonic palette expanded far outside that vernacular, does not lose sleep over this question.

So Dylan must have had an obsession with Junichi Saga’s Confessions of a Yakuza sometime between the book’s 1991 publication and the 2001 release of “Love and Theft”. The biographical novel focuses on the life and travails of a dying Japanese mobster as told from his deathbed to his doctor. Dylan lifts lines from it all over the album, twisting them to suit his needs. “Floater (Too Much to Ask)” is the most prominent example. Musically, the song borrows liberally from Bing Crosby’s 1932 recording of “Snuggled on Your Shoulder.” It’s a strange, impressionistic pairing. What’s strange is that, despite the music and lyrics coming from places that are seem distinctly un-Dylanesque, the song calls back to the swirling, surreal spaces Dylan conjured so easily in the 60s with tracks like “Desolation Row.” And yet on the whole the song is exemplary of Dylan’s work in the 21st century, sounding nothing like what had come before, even as it raised plenty of hysteric declarations of plagiarism in the press upon its release. But if nothing is really new, then originality comes from creating new configurations of what is already lying around. Few artists have ever been better at that than Dylan. – Ian Maxton

“High Water (For Charley Patton)”

As much found-art collage as an original composition, this in many ways announced Dylan’s 21st century project, which culminated in the recent 17-minute behemoth “Murder Most Foul.” “High Water” is named for blues legend Charley Patton. But it’s also for Robert Johnson, whose “I Believe I’ll Dust My Broom” is quoted; and for Big Joe Turner, referenced in the first verse, as well as for the hundreds of thousands affected by the Great Mississippi Flood of 1927. If there’s anything we learned from “Murder Most Foul,” it’s that Dylan believes there is a special power in evoking the past, even if all you’re doing is saying the names. Some have criticized Dylan’s tendency to quote from other sources, calling it plagiarism. However, one might argue that Dylan isn’t so much speaking for his referents as letting them speak for themselves—on some level, letting history speak for itself.

Dylan intentionally leads us back to Patton’s original, “High Water Everywhere,” whose title informs the title and the chorus of Dylan’s own song. In it, we see not only an account of the flood but also an account of systemic racism. Patton sings, “I would go to the hill country, but they got me barred,” alluding to the Red Cross’s treatment of Black families displaced due to the Mississippi flood. In the final line, he sings, there “was no one to be found” (echoed by Dylan in the line, “Folks are leaving town”)—200,000 African Americans lost their homes, and many families went north as part of the Great Migration. Dylan’s referentiality casts light on a web of interwoven threads of U.S. history which are impossible to disentangle—disaster, displacement, systemic racism and the history of popular music. -Tyler Dunston

“Moonlight”

In 2015, when Bob Dylan announced that he would release an album of Frank Sinatra covers that would eventually kick off a trilogy of reinterpretations of the Great American Songbook, some were surprised. Those shocked by this move may not have listened to “Love and Theft” for quite some time, or else they would have remembered that “Moonlight” made the inevitability of such an artistic left turn pretty obvious. Most of the album feels deliberately old-fashioned, as if Dylan is imbuing the musical genres and styles he grew up loving with new life, and this takes that idea to its extreme. It’s a jazzy torch song, the kind that would have been a hit for any number of big band crooners in the ‘40s. However, to call “Moonlight” a straightforward tribute would be a mistake; after all, when has Bob Dylan ever been really straightforward?

Rather than address the object of his fancy directly, Dylan uses flowery language, piling metaphors and figurative language upon each other to create this dizzying array of images that are striking in their beauty, even if their meaning is unclear. Dylan fans have read into the lyrics for years, and some debate whether the song is intended to be romantic or if it’s a murder ballad (the line about “twisted oaks that groan” indicates the latter, or at least some sort of sinister undercurrent). Dylan doesn’t seem interested in tipping his hand: no matter how twisted some of his images get, he returns to that simple plea that he delivers with a sincerity borrowed from Ol’ Blue Eyes: “Won’t you meet me in the moonlight alone?” An exhortation for a romantic encounter, perhaps? Or something darker? Whatever the case, it’s delivered with a level of craft and honesty from a time long past, an era which Dylan clearly holds dear. – Kevin Korber

“Po’ Boy”

In another assemblage, Dylan lifts from Confessions of a Yakuza again, throwing in some Marx Brothers humor and, yes, Shakespeare. But what is so incredible about Dylan’s songwriting method during this period is that he completely transforms the base material. “Po’ Boy” sounds like it was dug out of a record crate, an obscure 78 by some artist who cut three tracks for a combo recording and furniture company.

The tune is archetypal, as is its title figure. As always, Dylan plays games with the first person. The verses tend to start with a miniature scene, followed by the refrain, which seems to comment on them. But is Dylan the “Po’ Boy” of the title? Or is he the narrator, reeling off these absurd scenes in order to land punchlines like: “Called down to room service, says, ‘Send up a room.’” He’s both and neither, of course. But between the jokes are intimations of betrayal and regret – the room from the joke above is in a hotel called the Palace of Gloom.

The blues rag is a great canvas for Dylan to paint these scenes on. The song is jaunty, even as death and violence lurk. It is often remarked that Dylan’s worst records are the sound of a man who doesn’t give a shit, but “Love and Theft” sounds, for the first time in a decade or more, like the sound of a man having fun – cracking jokes, playing tricky literary games and calling on the pre-rock tunes of his youth to set the atmosphere just right. – Ian Maxton

“Sugar Baby”

American folk music has been part of Dylan’s musical DNA since the beginning of his career, but it wasn’t until the late ‘90s that the blues really became an equally important component. The two albums of traditional folk songs that he had recorded earlier that decade, Good as I Been to You and World Gone Wrong, seemed to have the effect of rebooting his musical instincts; after years of clumsy attempts to modernize his sound, Dylan was reacquainting himself with the songs and songwriters who had first inspired him. Here were Woody Guthrie and Ramblin’ Jack Elliott, of course, but here also were Robert Johnson and Muddy Waters, Charley Patton and Blind Willie McTell. Dylan had always drawn from these artists, but now he seemed to be speaking their language—lifting entire lyrical and musical passages as he went beyond rock ‘n’ roll and into a more primordial form of American music.

Like the Dock Boggs tune from which it takes its name, “Sugar Baby,” the final song on “Love and Theft”, is indebted to folk and blues without wholly belonging to either. It also borrows (steals, really) the melody and a key lyric—“Look up, look up, seek your maker ‘fore Gabriel blows his horn”—from Gene Austin’s “The Lonesome Road,” as well as a stately solitude that transcends genre. (A lot of Dylan’s closers share this quality, especially the epics like “Desolation Row,” “Highlands” and another entry on this list.) It all makes for a song that feels like a new American standard, an object that’s at once familiar and novel. “You went years without me,” Dylan harrumphs on the chorus, “Might as well keep going now.” He seems to be singing it as much for himself as for the object of his affections. – Jacob Nierenberg

“Cross the Green Mountain”

One of Bob Dylan’s best songs of the decade would have remained buried in the soundtrack of the forgotten and apparently execrable movie Gods and Generals. Fortunately, Tell Tale Signs pulled it from its purgatory to a more accessible space. “’Cross the Green Mountain” makes for its own mini-feature, a beautiful eight-minute meditation on war and loss among other topics. Dylan immersed himself in researching the period while writing and, whether that work specifically paid off or not, the song gets deep into both time and character, fit more for a fireside reread of Cold Mountain than for a movie grind.

Dylan extends the writing techniques that suit him so well. From its opening verse, the song carries a vague apocalyptic tone with a dream and a sea monster that reveal fundamental truths. Rather than staying as loose metaphor, though, the frame locates the specific, in this case a Confederate soldier suffering loss. We see the South burning (with religious overtones) as Stonewall Jackson dies; Alabama loses its stars. Dylan collects these moments along with his standard allusive approach, blending in the timely work of Walt Whitman along with other poets and, of course, the Bible. The original content and the references coalesce into a moving ode.

“Cross the Green Mountain moves steadily, with its atmosphere, largely provided by an organ, more valuable than its individual elements. Even so, the song relies on a careful arrangement. Larry Campbell’s violin works perfectly, and the subtle moves in dynamics and tension keep the song from feeling repetitive despite its consistent structure. The final chord captures the singer’s love, regret and stoicism, the shift to silence befitting a sad piece that lingers well after its final revelations. – Justin Cober-Lake

“Thunder on the Mountain”

Opening Modern Times is this prototypically rocking Dylan, all choogling, blues-y groove and enigmatic lyrics. Allegedly inspired by Dylan having seen Alicia Keys’ performance at the Grammys (hence her seemingly out-of-left-field appearance in the second verse), he spends most of the lyric playing around with Biblical imagery. But it’s this second verse that really makes the song stand out, with Dylan’s admiration of a fellow artist coming through in lyrics that otherwise don’t make much sense within the broader context. This is so much so that when Wanda Jackson cut “Thunder on the Mountain,” she scrubbed Keys entirely in favor of Jerry Lee Lewis; in other words, it’s a sort of choose-your-own-adventure verse that could be appropriated by and attributed to whomever the singer wants.

After opening with some old-fashioned fire and brimstone, the non-sequitur, “I was thinkin’ ‘bout Alicia Keys, couldn’t keep from crying,” is something of a head-scratcher. He ties it back in describing her as having been “born in Hell’s Kitchen,” but goes off the rails again with the follow-up couplet: “I’m wondering where in the world Alicia Keys could be/ I been looking for her even clear through Tennessee.” And then, just like that, she vanishes completely, and Dylan returns to his enigmatic imagery. It’s a strange lyrical detour surrounded by such brilliant verbal choices as rhyming “sons of bitches” with “orphanages” and the made-for-each-other couplet, “I got the pork chops, she got the pie/ She Ain’t no angel and neither am I.” “Thunder on the Mountain” is typically ambiguous Dylan imagery with a puzzling curveball thrown in for good measure. Nearly half a century into his legendary career, he still managed to keep people scratching their heads while tapping their feet and nodding along to the infectious flow of his delivery and impeccable backing musicians. – John Paul

“Spirit on the Water”

“Spirit on the Water” is a song that no young person could write. It moves at a leisurely pace, nearly eight minutes of the type of balladeering Dylan would explore throughout most of the 2010s. At face value, it is a song about unrequited love, a paean from a lover terrified of being thrown over. But there is something deeper at play here.

The song’s title and first line spring from the Bible verse: “And the earth was without form, and void; and darkness was upon the face of the deep. And the Spirit of God moved upon the face of the waters.” Dylan simplifies this a little with:Spirit on the water/ Darkness on the face of the deep.” So, just why is a simple love ballad digging deep into Biblical allusions?

Late in the song, Dylan complains, “I wanna be with you in paradise/ And it seems so unfair/ I can’t go back to paradise no more/ I killed a man back there.” It is possible that this object of affection is dead and Dylan can’t reach her in heaven for past sins, but that’s too literal. Instead, the dead man likely represents some sort of transgression the narrator did in the past, making it impossible to return to whatever halcyon state the relationship used to resemble. However, the narrator isn’t the only one to blame. “Why can’t you treat me right/ You do good all day/ Then do wrong all night,” he claims.

Dylan also cribs a line from Sonny Boy Williamson’s “Black Gal Blues”: “Lord knows I’m wild about you, black gal/ You ought to be a fool about me.” Compare that to Dylan’s couplet: “I’m wild about you, gal/ You ought to be a fool about me.” The addition this quote moves the song squarely into the secular. It makes sense, since Dylan has recast himself as an elder bluesman at this point in his career. Dylan may scoff at people who look for threads like these in his songs, but it’s just part of the fun for Dylanologists to sort through the crumbs, allowing songs like “Spirit on the Water” to work on so many different levels. – David Harris

“Rollin’ & Tumblin’”

It’s weirdly apt that Modern Times starts to pick up steam with a track that originated in 1929. Beginning with Hambone Willie Newbern and following a path that included Robert Johnson, Muddy Waters and Led Zeppelin, “Rollin’ and Tumblin’” seems like the kind of off-the-cuff blues number a veteran rocker could pull off in his sleep. But the lyric’s fascinating transformation over the decades points to this as a nearly apocalyptic vision that could only come from an old body–and soul–like Dylan’s.

Tracing the song through the years reveals remarkable shifts in tone. The twinned title gerunds sound like a throwaway sexual romp, but the image is rich and layered—appropriately like a biscuit, which drives the lyric of early renditions like Robert Johnson’s “If I Had Possession Over Judgement Day,” when insomnia leads to an acute anxiety: “Boy I woke up this morning, my biscuit roller gone.” [Some interpret that “biscuit roller” as a woman who done him wrong, but it’s hard not to hear it as a fear of castration.] Zep’s variation, “Traveling Riverside Blues,” is pure sexual prowess, complete with lemon squeezing, but Dylan smokes it at a tempo and tone much like Muddy Waters’ 1950 version, is far beyond sowing wild oats. After his own sleepless night he laments, “I must have bet my money wrong,” specifying with a lascivious glee, “Some young lazy slut has charmed away my brains.

This is the kind of doomed bluesman persona Dylan dreamed of embodying in his early career, and now he has the grizzled voice and fatalistic wisdom to sell it as he gets closer to judgement day—which he may well be presiding over: “The night’s filled with shadows, the years are filled with early doom/ The night’s filled with shadows, the years are filled with early doom/ I’ve been conjuring up all these long dead souls from their crumbling tombs.” That primeval blues structure with the repeated line seems to point to the inevitability of his fate, and everybody’s: your time will come to pay the piper. That Dylan conveys this in six minutes of choogling music with humor and brimstone proves he’s one of the most possessed of all rock ‘n’ roll preachers. — Pat Padua

“When the Deal Goes Down”

Though Bob Dylan namechecks Alicia Keys in the opening moments of Modern Times, Scarlett Johansson appears in the video for “When the Deal Goes Down.” Directed by Bennett Miller, “Deal” is one of the few Dylan songs to actually get an official music video release. The short film feels like the polar opposite of the tragic nostalgia featured in Lana Del Rey’s “Video Games” as Johansson appears in what feels like wholesome home movies from decades past.

Dylan may be mining nostalgia in Modern Times by quoting the Bible, old blues singers and Ovid, but “When the Deal Goes Down” is a song pointed towards the end of life. “We live and we die/ We know not why/ But I’ll be with you when the deal goes down.” This isn’t the type of deal Lou Reed is singing about in “I’m Waiting for the Man,” but the final deal, something Dylan seems to have been exploring since the late ‘90s.

Yet, Dylan isn’t looking at death with fear. Instead, he chronicles all the different emotions one experiences whilst being alive, knowing that whomever he loves is by his side when it’s time for one of them to pass on. The music video brims with life as we watch Johannson play badminton, cuddle with children and lounge in a hammock. Miller plays up the nostalgia but the video is looking back while the song stretches towards the end.

If the early ‘90s were a time for Dylan to air out his influences by doing stripped-down cover songs, the ‘00s found the musician fusing their words and melodies with his own. “When the Deal Goes Down” makes no apologies for its inspiration, using the melody of Bing Crosby favorite “Where the Blue of Night (Meets the Gold of Day)” as its backbone. For those crying plagiarism, Dylan headed them off at pass, telling the Los Angeles Times that many of his melodies have come from other sources from hymns to Carter Family tunes. This sort of songwriting tradition has become lost in a mire of legal tangles. Dylan is doing what any good bluesman has always done. And “When the Deal Goes Down” is the perfect distillation of inspiration and invention. – David Harris

“Workingman’s Blues #2”

Dylan’s most popular political tunes have been played at many a rally and demonstration, but for all their affective power, they lack specificity. It’s their greatest weakness as political pieces, but their greatest strength as enduring pieces of music. They aren’t scathing, incisive critiques of a political system – they’re vague by design, which is why they’ve become broad, hopeful bits of liberal agitprop. This, despite the fact that they came into being at the last real high watermark of the American left. But remember, the folk scene that directly preceded Dylan and after which he modelled himself was crawling with communists. In that tradition, “Workingman’s Blues #2” is a worthy entry.

Released in 2006, the song arrived a decade too early for some idiot op-ed writer to declare it Dylan’s ode to the white working class. It doesn’t take a genius to figure out that a song with lyrics like “The buyin’ power of the proletariat’s gone down” is more Marx than MAGA, though. The song does convey a deep melancholy over a fading way of life, but that way isn’t some nostalgic idyll filled with good-paying jobs and racial homogeneity. Rather, the song looks back to a time when working people recognized class war for what it was and fought back, contrasting that with the present resignation. It’s a song about the power of solidarity. All over the track are intimations of violence against workers and calls to form new alliances and fight back – and Dylan lifts lyrics from Woody Guthrie, Big Joe Williams and Robert Johnson to drive his point home.

The instrumentation is simple and straightforward. The track isn’t dynamic – it’s a dirge. It’s the sound of a song meeting its moment, even if that moment hadn’t yet appeared – “No man, no woman knows/ The hour that sorrow will come” hits different post-Recession. At a time when the poor and working classes are as diverse as they’ve ever been in this country – and perhaps as powerless as they’re ever been – the song’s powerful closing lines do something more effective than asking us to listen for an answer blowing in the wind, they point to our common enemy. – Ian Maxton

“Nettie Moore”

Oh, I miss you Nettie Moore/ And my happiness is o’er” Dylan sings, quoting word-for-word Marshall S. Pike and James Lord Pierpont’s “Gentle Nettie Moore” from 1857, to form the backbone of a song stepped in U.S. folk and blues traditions. He takes the direct quotation seriously; there’s perhaps a bit of playfulness in the way he retains “o’er” to maintain the full rhyme of “o’er” and “Moore.” Throughout, the lines expand and contract, build in intensity only to be diffused. The melody is stirring but restrained, never quite allowing for release. Lyrically, the song is a mix of celebration and mourning—an elegy of sorts—for music itself, as suggested by Dylan’s source material, which highlights Nettie Moore’s “gentle voice.” So, Dylan celebrates the voices of the blues and folk musicians who came before him and directly informed his work.

The song is not only full of direct quotes—appearances by Charley Patton, Robert Johnson—but also a plethora of ubiquitous tropes of music in the blues and folk traditions. The song is not only a celebration but something of a farewell, one that conflates romantic love and loss as well as the love and loss of a music and history. It is also a personal account, as Dylan conflates the myth of a version of himself with American music, the story of which is deeply entangled with mythology and history—from the Faustian fiction of Robert Johnson’s legendary guitar skill to the very real histories of oppression that blues and folk music arise out of and document. It is one of the great ironies of the history of the blues that the racial discrimination which they so often documented is itself responsible for the fact that the early history of the blues is so poorly documented. Dylan knows it is impossible to fill these gaps, but he weaves an incomplete tapestry anyway. (We may see his supposed “plagiarism” as a kind of scattered history.) Throughout, Dylan pairs heartfelt sincerity with humor, wit and a wide-ranging sense of scope. He’s building on the myth of American music, as well as his own myth, all the while acknowledging that it’s impossible for one song to cover it all. – Tyler Dunston

“The Levee’s Gonna Break”

“The Levee’s Gonna Break” has layers of meaning baked into it. For one thing, the title and first few lines are borrowed from a blues standard made famous by Led Zeppelin. Moreover, the song came out only a year removed from the destruction that Hurricane Katrina had wrought on New Orleans, which made the invocation of levees pretty timely. Then again, what should we have expected from an album called Modern Times? The album frequently found Dylan engaging with the modern world in a way that his previous two albums defiantly refused to do, and while “Levee” borrows its structure, title and lyrics from the past, its concerns and barbs are directed very much at the villains of the present.

Naturally, while the song definitely feels inspired from the fallout from Katrina, “Levee” isn’t explicitly about anything that happened during the disaster or the government’s mishandling of the aftermath. Instead, Dylan uses a rambling 12-bar blues to tell a story of someone finding rebirth after reaching their lowest ebb. Crucially, this low point doesn’t come as a result of the speaker’s own folly; Dylan’s refrain of “Some of these people gonna strip you of all they can take” and repeated reference to an unseen “they” indicate that the speaker has been beaten down and robbed by an unseen force. Crucially, though, “The Levee’s Gonna Break” isn’t just the story of a personal or spiritual downfall; there’s rebirth in the narrative as well. Dylan’s speaker isn’t full of despair; he sounds liberated. Even as elements of reality seep in, he sounds undeterred in his belief that a better day will come and that these difficult moments will soon be in the past. It’s a story of resilience as much as it is a story of destruction, and given the context of its release, it’s clear that this was a song Bob Dylan made for someone other than himself. – Kevin Korber

“Ain’t Talkin’”

“Ain’t Talkin’” is one of the true masterpieces of this final third of Dylan’s career, a sterling example of how he can adapt lines from folk songs and poetry into compositions that feel entirely his own. Two lines that appear in every other verse—“Ain’t talkin’, just a-walkin’” and “Heart burnin’, still yearnin’”—are lifted from the Stanley Brothers’ “Highway of Regret,” but the song feels more like Dylan’s reinterpretation of “The Wayfaring Stranger,” the source of the “world of woe” lyric. (There’s also a nod to the works of Ovid, who you’ll be seeing again on this list.) Only the narrator of “The Wayfaring Stranger” is hoping for deliverance, or to return home, while the character Dylan sings as in “Ain’t Talkin’” is just trying to stay alive in a world gone wrong.

Of course, the end times are hardly new ground for Dylan to cover, but rarely has the man portrayed himself as such a ruinous and malevolent force, akin to DMX or Anton Chigurh: A criminal prosecutor might be driven to press charges after hearing Dylan mutter “If I catch my opponents ever sleepin’/ I’ll just slaughter ‘em where they lie.” To that end, his vow that “I’m a-tryin’ to love my neighbor and do good unto others/ But oh, mother, things ain’t goin’ well” practically reads as an admission of guilt. Unlike the Stanley Brothers song that inspired its title, “Ain’t Talkin’” betrays no trace of regret, just a thirst for revenge. It’s a mode Dylan has only written in a few times, and bettered even fewer. -Jacob Nierenberg

“Beyond Here Lies Nothin’”

Many have taken the title of this song to be a quote from Ovid, though few have commented on it further, beyond noting that it’s in keeping with Dylan’s fascination with myth and mythmaking. However, when we turn to the line in question, it’s interesting to note that it is not from the fantastic, mythological tales of the Metamorphoses but from Ovid’s poems written while he was in exile: “longius hac nihil est, nisi tantum frigus/ et hostes, et maris adstricto quae coit unda gelu. [Beyond this there is nothing, save only the cold/ and enemies, and the wave of the sea which coalesces in frozen ice.]” There is an apparent reversal of the source material in Dylan’s version. While Ovid was exiled by Augustus, alone in a land far from home where no one speaks his language, Dylan is at home with “the only love” he’s ever known. Outside of their love, they have “nothing to call [their] own.”

Both writers tell a story of alienation, but Dylan’s story is one of alienation from everything with a crucial exception. As such, it’s as much about refuge—in another person—as it is about alienation. This refuge is such that the social world melts away—beyond it there is nothing “but the moon and stars.” The emphasis on the nothing which characterizes the world outside their love, along with qualifiers like “As long as you stay with me” and “For as long as love will last,” highlights the significance of Ovid’s poem for this speaker. Ovid’s vision of exile is in many ways the same as the one Dylan hints at in lines like, “Don’t know what I’d do without it/ Without this love that we call ours.” Without this love, his exile would be the same as that of the ancient poet. Dredging up “the mountains of the past” through Ovid’s poem, Dylan conjures the fear of loss that goes hand in hand with his vision of love. – Tyler Dunston

“My Wife’s Home Town”

Using Willie Dixon’s well-known and beloved blues standard “I Just Want to Make Love to You” as a starting point, Dylan and Grateful Dead lyricist Robert Hunter repurposed the original’s format, loose melodic structure and prototypical blues cadence to come up with the rollicking, tongue-in-cheek “My Wife’s Home Town.” Instead of Dixon’s carnal yearning, Dylan flips the original’s sentiments on their ear and delivers something of an extended blues riff on the old “take my wife, please” joke formula. Where Dixon lists all the things he doesn’t want the object of his lust to do, Dylan sits right down and lays out his desire to just take a load off: “Well, I didn’t come here to deal with a doggone thing,” he croaks, before delivering the kicker line, “I just wanna say that hell’s my wife’s home town.”

It’s all a bit silly and clearly taking the piss out of the typical blues sentiments, but it also works simply because it rides along on the well-worn path of familiarity in terms of form and structure (i.e. the stock-in-trade I-IV-V blues progression). Thematically, it shows the flip side of what can happen to those who pine away for the object of their affection, with Dylan lamenting that he’s pretty sure she’ll make him kill someone some day and that “[his] love for her is all [he] know[s].” In other words, he’s effectively cursed, stuck with hell’s princess for the remainder of his days and he just wanted folks to recognize that. “She can make you steal, make you rob/ Give you the hives, make you lose your job,” he warns, “Make things bad, she can make things worse/ She got stuff more potent than a gypsy curse.” All things to consider when pining after that voodoo woman archetype so popular within the blues idiom. In other words, be careful what you wish for. – John Paul

“I Feel a Change Comin’ On”

Co-writing this one with Robert Hunter, Dylan wrote the lyrics inspired by Billy Joe Shaver’s “Ain‘t No God in Mexico,” a hit for Waylon Jennings. As he did so often this decade, Dylan takes on an outlaw’s lament, not about evading an earthly law enforcement but running afoul of a higher power. He’s restless, “lookin’ the world over.” He’s concerned about his loved one’s soul: “I see my baby comin’/ She’s walking with the village beast.” And as he nears the end of his days, it’s nearly time for the great reckoning: “I feel a change comin’ on/ And the last part of the day’s already gone.

The easy tempo, and David Hidalgo’s accordion, sets up this autumnal reflection with a light touch, but it’s filled with heavy regret: “Well now what’s the use in dreaming?/ You got better things to do/ Dreams never did work for me anyway/ Even when they did come true.” Over the course of his long career, Dylan has pretty much achieved anything a musician would ever want, but to what end? Another line seems to echo The Room: “Well, life is for love/ And they say that love is blind.” Who knows if Dylan ever attended a midnight screening of Tommy Wiseau’s notorious folly, but deliberate or not, the resonance speaks to the fine line an artist walks between triumph and disaster.

After an improbably fertile late-career decade, Dylan was about to change again, shifting gears to, of all things, Christmas music, and a grizzled lounge singer’s attempts at the Great American Songbook. With an unmistakable voice that defines a certain rock royalty, Dylan has always remained himself, but rather than settle into a predictable groove, he was ready to upend expectations once again, however frustrating those ends might be. — Pat Padua

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