The 25 Best Bob Dylan Songs of the 21st Century

In October 2014, Bob Dylan was wrapping up a three-night stand at the Dolby Theatre in Hollywood, California, home of the Oscar broadcast, when he cut “Blowin’ in the Wind” from his set list and instead closed with Frank Sinatra’s 1964 song “Stay With Me,” written by Carolyn Leigh and Jerome Moross. Nobody knew it that night, but it was the public’s first glimpse at a new era of Dylan’s career, in which he’d devote three straight albums (2015’s Shadows in the Night, 2016’s Fallen Angels, and 2017’s Triplicate) to standards associated with Sinatra. One of his most successful interpretations was this first one, where he takes a tale of helplessness and sorrow and somehow makes it sound even more desperate than the original. Most people in the crowd that L.A. night would probably have preferred “Blowin’ in the Wind,” but Dylan has never been one to give his audience exactly what they want. A.G.

Just when we thought Dylan couldn’t surprise us with any more curveballs, he released a Christmas record. At the centerpiece of 2009’s Christmas in the Heart is a polka-meets-klezmer version of “Must Be Santa,” taking its zany inspiration from an earlier cover by the Texas outfit Brave Combo. In a bonkers video directed by Nash Edgerton, Dylan appears at a boisterous Christmas party, dressed in a silver wig and bowler hat while throwing a few former presidents’ names in with Santa’s reindeers: “Dasher, Dancer, Prancer, Vixen/Eisenhower, Kennedy, Johnson, Nixon!” The rest of Christmas in the Heart is surprisingly great — a collection of classics so warm and jolly it left critics thinking there had to be a layer of irony behind it. “Critics like that are on the outside looking in,” Dylan told Bill Flanagan. “They are definitely not fans or the audience that I play to. They would have no gut-level understanding of me and my work, what I can and can’t do — the scope of it all. Even at this point in time they still don’t know what to make of me.” A.M.


Dylan toured with Merle Haggard in 2005, which might be why he chose to write a sequel to Haggard’s upbeat 1969 blues stomper for Modern Times the following year. While Haggard chose to write about a working-class family man who gets through the weeks by blowing off steam in the tavern on the weekends, Dylan sings about someone who is out of options: “They burned my barn, they stole my horse, I can’t save a dime.” Instead, the character surveys bruised relationships and lost battles on this hidden gem. The character’s life starts looking up by the end of the song, though his bitterness remains. “Got a brand new suit and a brand new wife/I can live off rice and beans,” Dylan sings. “Some people never worked a day in their life/Don’t know what work even means.” P.D.

The romantic ballad “Autumn Leaves” has been recorded by everyone from Frank Sinatra to Bing Crosby to Nat King Cole and Doris Day — but all of those artists tackled the song before the age of 50. When Dylan recorded it for 2015’s Shadows in the Night, it took on a whole new meaning. Here’s a 74-year-old crooner looking back on his life with nostalgia and more than a little regret. Backed by a swirling pedal steel guitar, he yearns for the past: “Since you went away, the days grow long/And soon I’ll hear old winter’s song.” Dylan would go on to release two more collections of standards, but there’s a reason he’s performed “Autumn Leaves” 237 times over the past five years. It fits in with his originals better than nearly anything else from this period. A.M.

Dylan was always a hip-hop head — ever since he spat bars on old-school rap legend Kurtis Blow’s “Street Rock” in the Eighties. In his memoir, Chronicles, he raves about getting his mind blown by N.W.A, Public Enemy, and Ice-T. “These guys weren’t standing around bullshitting,” Dylan wrote. “They were beating drums, tearing it up, hurling horses over cliffs. They were all poets and knew what was going on.” “It’s All Good” flips the rap catchphrase into an accordion blues rant, for a tone that’s somewhere between “Gangsta Gangsta” and “Groom Still Waiting at the Altar.” Dylan sings about the whole world going up in flames — lying politicians, cheating lovers, cops on the prowl, violence, blood, sin, misery. But he cackles wildly as he chants, “It’s aaaaaaaall good!” R.S.

By 2001, Dylan had been playing around with blues forms for 40-odd years. But he’d rarely sounded like he was having more fun with the genre than he did on “Lonesome Day Blues,” a loose and raucous 12-bar shuffle in the spirit of classics like “Leopard-Skin Pill-Box Hat,” where he throws narrative out the window and simply riffs. Even singing about his “sad and lonesome day” in the first verse — nodding to Leroy Carr and Scrapper Blackwell’s 1934 tune “Blues Before Sunrise” and rasping out his words in a voice that Rob Sheffield, in his original Rolling Stone review of Love and Theft, likened to the growl of “a bear cat that hasn’t eaten since the Eighties” — Dylan comes off sly and a little rakish. By the fourth verse he’s going on about a woman named Samantha Brown, saying that they cohabitated for “four or five months” while denying that he ever “slept with her even once.” (Strangely, Dylan likely borrowed this bit from Confessions of a Yakuza, an obscure 1989 nonfiction book by Japanese doctor Junichi Saga.) What the song lacks in coherence, it makes up for in charisma, with Dylan selling each punchline — “You’re gonna need my help, sweetheart/You can’t make love all by yourself” — like the “song-and-dance man” he’d always insisted he was. H.S.

For many fans, the three-CD set of standards Triplicate felt like absurd overkill coming after two previous volumes that covered the same territory. But it has plenty of fascinating moments. Dylan ends its long journey with a somberly searching torch song originally written in 1929 by Jerome Kern and Oscar Hammerstein, and recorded by Frank Sinatra, Billie Holiday, and Ella Fitzgerald, among others. “Why was I born?/Why am I living?/What do I get?/What am I giving?” Dylan croons, his gruff moan giving these lovelorn riddles an existential weight, as if, having lived deep into his seventies, he’s wondering more urgently than ever how to make his life matter. As always, he makes the story his own. J.D.

At many of his concerts in the 2010s, Dylan would play this song onstage in front of a background that looked like Van Gogh’s Starry Night. It matched the feeling of this soulful track, which recalls Fifties doo-wop before it turns into a murder ballad. (Fans have noticed that the song sounds a lot like Bobby Fuller’s “A New Shade of Blue,” and Charlie Sexton’s guitar solo recalls the melody of “Blue Moon.”) By the end, it’s clear Dylan doesn’t care about Charlotte the harlot, Mary in green, or the fairy queen — there’s only one lover on his mind, and Two-Timing Slim isn’t going to keep them apart. “Who’s ever heard of him?” Dylan asks. “I’ll drag his corpse through the mud.” P.D.

“I’d make this record no matter what was going on in the world,” Dylan told Rolling Stone in 2006 about Modern Times. “I wrote these songs in not a meditative state at all, but more like in a trancelike, hypnotic state.” That trancelike feeling defines “Spirit on the Water,” a nearly eight-minute love song where Dylan quotes the Bible and Sonny Boy Williamson. Dylan sings about the joy his lover brings him, and waits till the end to disclose a cruel and simple twist of fate: “I wanna be with you in paradise/And it seems so unfair/I can’t go to paradise no more/I killed a man back there.”  P.D.

Like most of 2009’s Together Through Life, “Beyond Here Lies Nothin’“ was co-written with Grateful Dead lyricist Robert Hunter. It opens the album with a shadowy image of last-ditch romance as guard and guide in a barren world. With Mike Campbell’s guitar lashing against rumbling drums, and the forlorn feel of Donnie Herron’s trumpet and David Hidalgo’s accordion, the song has a mysterious noir feel, as if the narrator is leaving out almost the entire story of how he brought his lover to a place where it’s just them, the moon, the stars, and the empty boulevards; you get the sense that whatever he has planned next is only going to make things worse, but you can’t help but be impressed by his doomed resilience. J.D.

Dylan wrote a series of soundtrack songs for films between Love and Theft and Modern Times. Perhaps the best is “Tell Ol’ Bill,” which he wrote for the film North Country, starring Charlize Theron. With a title that goes back to 1927 and a melody that may have been inspired by the Carter Family, Dylan tells the story of a roving loner trying to survive as judgment day approaches. (“You trampled on me as you passed/Left the coldest kiss upon my brow,” Dylan sings in one killer line. “All of my doubts and fears have gone at last/I’ve nothing more to tell you now.”) “Tell Ol’ Bill” is a favorite among hardcore Dylan fans like Tony Attwood at Untold Dylan, who called it “one of Dylan’s two greatest works of all time” and wrote a fascinating piece tracing its origins through several bootleg versions. As documented there, the singer tried a few approaches, from one version that echoes the groove of “Thunder on the Mountain” to another that’s more reminiscent of “It Takes a Lot to Laugh, It Takes a Train to Cry.” “Gradually,” Attwood writes, “Dylan moves towards the masterpiece that we have come to know.” P.D.

Over a descending chord progression that becomes relentlessly more intense, Dylan surveys the wreckage of a messy life. Regrets, he has a few: The love that he shared with someone else has long slipped away, those close to him are gone, and even his enemies are dead. It sounds a lot like The Irishman. The small details are what make this song, like when Dylan says, “I ain’t seen my family in 20 years/That ain’t easy to understand, they may be dead by now/I lost track of ’em after they lost their land.” P.D.

A bookend of sorts to “Murder Most Foul,” the contemplative scene-setter that opens Rough and Rowdy Ways is another song where Dylan seems to be considering his place in the constellation of great musicians and artists through the ages. This time, the man of many moods is in a more playful one. He shouts out William Blake and Edgar Allan Poe, slyly quotes Bowie and the Eagles, and gets in some sharp one-liners (the title phrase rhymes with “I paint landscapes, and I paint nudes” and “I drive fast cars, and I eat fast foods”). Some of his bons mots are absurd verging on insane, like when he compares himself to Anne Frank, Indiana Jones, “and them British bad boys, the Rolling Stones.” When an interviewer politely inquired as to the intent behind that line, Dylan parried: “Every line has a particular purpose. Somewhere in the universe, those three names must have paid a price for what they represent, and they’re locked together. And I can hardly explain that.” In other words, buzz off, Mr. Jones — which is really what he’s saying throughout “I Contain Multitudes.” Walt Whitman, in his famous line, was making a case for the liberating possibilities of contradiction. Dylan uses it to tell anyone who’s doubting the workings of his genius (including, perhaps, himself) to ease up and have a little fun. S.V.L.

“Ever since the British burned the White House down” — that would be the War of 1812, history fans — “there’s a bleeding wound in the heart of town.” That’s where Dylan locates “Narrow Way,” a highlight from Tempest. The song has the edge of his most caustic Sixties putdowns, back when his idea of a good time was sneering “She’s Your Lover Now” or “Ballad of a Thin Man” or “Positively 4th Street.” Except “Narrow Way” has an extra 50 years’ worth of venom in it. Dylan rains down Biblical threats and curses on his enemies, quoting the Mississippi Sheiks and the Book of Daniel, over a seven-minute high-speed guitar/fiddle blues shuffle. “Your father left you, your mother too,” Dylan snarls. “Even death has washed its hands of you.” It’s the most gloriously mean moment on Tempest, one of his meanest albums. R.S.

One needs to know nothing about the 2007 box-office bomb Lucky You to become enchanted by the aching beauty of “Huck’s Tune,” even though Dylan wrote it specifically for the movie and it makes explicit references to characters and plot developments. Divorced from that context, the lush, dreamy song becomes about the tragedy of sacrificing love to chase an impossible dream. “From my toes to my head, you knock me dead,” Dylan sings. “I’m gonna have to put you down for a while.” Much like he did with “Things Have Changed” seven years earlier, Dylan wrote the song for director Curtis Hanson after watching an early version of Hanson’s film. It’s Dylan’s best straight-up love song of the 2000s, and it easily could have earned him a second Academy Award had the movie been successful. A.G.

Can’t you hear that Duquesne whistle blowing — and more importantly, what’s it trying to tell you? The deceptively jaunty Robert Hunter co-write that opens Tempest dances around all kinds of high-minded and low-down possibilities for what its central image represents without settling on an answer. Half the time, the whistle sounds like the last trumpet of the apocalypse (“Blowing like it’s gonna sweep my world away”); just as often, it’s got a more carnal undertone (“Red light glowing/Blowing like she’s at my chamber door”). The whistle could be a symbol of music’s redemptive power (“Blowing like it’s gonna blow my blues away”), a threat from the grim reaper (“Blowing like it’s gonna kill me dead”), or a sign from a saint on high (“I can hear a sweet voice steadily calling/Must be the mother of our Lord”). Some interpretations hold that it’s the sound of a devastating 2011 tornado in Duquesne, Missouri; others have noted a resemblance to a 1930 tune by New Orleans jazz great Jelly Roll Morton. Maybe it’s all those things at once, a spooky echo of all the desires and fears bouncing around our singer’s head late at night. Or maybe it’s just a train, speeding down the tracks to eternity or the next station. S.V.L.

As Dylan reclaimed control of his music, he pushed toward a sound in his head that dated back to the Forties and Fifties — a band playing live in a room, ideally all into the same microphone. “Thunder on the Mountain” enters with an unmistakably live flourish of splashing cymbals and blues licks before kicking into a song that lands somewhere between rockabilly and Western swing. Per the book of Exodus, “thunder on the mountain” is how God likes to announce Himself, and the song has some not-atypical judgment-day-is-coming, woe-to-mankind overtones, but this time Dylan seems pretty cheerful about it all. Someday, yeah, he hopes to “stand beside my king,” but in the meantime he’s put his pitchfork on the shelf while pursuing more earthly concerns: “I’ve sucked the milk from a thousand cows,” he boasts. He also throws in a passing tribute to Alicia Keys (“When she was born in Hell’s Kitchen, I was living down the line…”), modeled after Memphis Minnie’s tribute to a fellow blues pioneer. “I was thinking about Ma Rainey,” she sang 66 years before Dylan. “Wonder where could Ma Rainey be/I been looking for her/Even been in old Tennessee.” A.G.

The weariness Dylan sings about in the somber folk blues “Nettie Moore” is archetypal, pulling in references from Marshall S. Pike and James Lord Piermont’s 1857 song “Gentle Nettie Moore” and the folk traditional “Moonshiner.” But it hits home because it feels so personal: He sings about being a singer “in a cowboy band,” wandering a world that’s “gone black before my eyes,” with only the faint image of his lover waiting back home to guide him through the wreckage. “I’d walk through a blazing fire, baby,” he sings, “if I knew you was on the other side.” J.D.

Dylan usually feels right at home in the dark. But in “Key West (Philosopher Pirate),” he goes all the way into “the land of light” for the nine-minute accordion ballad of a grizzled outlaw hiding out in Florida, hounded by his memories. It’s a stunner from the new album — and one of Dylan’s most quietly devastating ruminations. He’s in a promised land of sunshine — as he sings, “Key West is the place to be if you’re looking for immortality.” But he’s alone except for his radio, confessing, “I’m searching for love, for inspiration, on that pirate radio station.” And he’s still haunted by desire, even amid the hibiscus flowers and fishtail palms, growling, “I play gumbo limbo spirituals/I know all the Hindu rituals.” In Dylan songs, Florida is usually just a place you run to when you need to duck the law, as in “Po’ Boy” or “Tweeter and the Monkey Man.” But “Key West” is something new — when he pleads, “Radio signal, play ‘Rescue Me’/I’m so deep in love that I can hardly see,” he sounds truly tangled up in blue. R.S.

The relentlessly vicious “Pay in Blood” felt shocking when it came out, and a decade later it ranks among Dylan’s most searingly prophetic moments, an image of dumb, evil power flexing its amoral muscle on the neck of the weak. “I pay in blood, but not my own,” he growls, licking his chops as the song’s weirdly optimistic-feeling drive adds another level of grisly irony — as if its very anthemic lift is there to mock the people its narrator has crushed. In 2012, the lyrics seemed to evoke centuries of American violence, from slavery to disastrous foreign invasions. Today it sounds even more tragically urgent: Put it on and you can almost see Donald Trump trudging through Lafayette Square and red-state governors rushing to reopen as the death toll ticks higher. When this song becomes irrelevant, we shall be released. J.D.

“To me it’s not nostalgic,” Dylan retorted, forever prickly, when an interviewer used that word in reference to the 17-minute song he released in the spring of 2020. “I don’t think of ‘Murder Most Foul’ as a glorification of the past or some kind of send-off to a lost age. It speaks to me in the moment.” Here’s where Dylan’s head is right now, then, as the world spins off its axis once again. He’s thinking about John F. Kennedy’s assassination in November 1963, yes, but that quote is an important hint: He’s less interested in the historic truth of what happened in Dealey Plaza nearly 60 years ago than he is in how it made him feel, then and now. The longer “Murder Most Foul” goes on, the more shocked, hurt, and lost Dylan sounds. He’s reaching out for reassurance from the universe that just knocked him sideways. It could come from Charlie Parker or the Eagles, Little Richard or Thelonious Monk, “Another One Bites the Dust” or the Moonlight Sonata. The specific names he asks the late Wolfman Jack to play on his cosmic radio hour are less important than the sheer quantity of them. It’s as if the Nobel Prize made Dylan want to extend that same respect to every other popular musician whose work deserves to be canonized. As the final verses roll on, he sounds like he’s naming every song he can before we forget them, inscribing them all in a Book of Life expressed in the form of a midnight playlist. S.V.L.

“Mississippi,” God damn. Precisely what befell Dylan’s narrator during his ill-fated extra 24 hours in the deep South remains unclear — just as we never really learned what was bugging that guy who got marooned in Mobile, Alabama. Dylan wrote “Mississippi” in the Nineties and took at least two wildly different shots at the song in the studio during the Time Out of Mind sessions, before shipping it off to Sheryl Crow, who released a solid uptempo version in 1998. But Dylan and his touring band nailed the definitive version for Love and Theft, anchored by an ascending mandolin riff (as Eyolf Østrem’s fantastically geeky Dylan-for-musos site points out, this is one of the first Dylan songs since “Like a Rolling Stone” with a chord progression that climbs upward) and a throaty vocal filled with equal parts regret and hope. “You can always come back,” he sings, before undercutting the optimism: “But you can’t come back all the way.” (He rhymed that with the phrase “cold as the clay,” plucked from the old cowboy song “Streets of Laredo.”) B.H.

Dylan has a long history of wrapping up albums with epic-length, lonesome-sounding songs, from “Desolation Row” in 1965 (11:21) and “Sad-Eyed Lady of the Lowlands” in 1966 (11:22) to “Highlands” in 1997 (16:31). “Ain’t Talkin'” is short by those standards (a mere 8:48), but in that time it packs allusions to bluegrass duo the Stanley Brothers, the traditional folk song “The Wayfaring Stranger,” and the ancient Roman poet Ovid. It’s a song about a journey through a desolate, violent landscape straight out of Cormac McCarthy’s The Road, and nearly every line drips with doom and dread. This is Dylan at his bone-chilling best. “Now I’m all worn down by weepin’,” he sings. “My eyes are filled with tears, my lips are dry/If I catch my opponents ever sleepin’/I’ll just slaughter them where they lie.” He attempted the song live many times over the years, but the studio rendition is the definitive one, and the perfect way to conclude an album as dark and world-weary as Modern Times. A.G.

The Mississippi River flooded in 1927, devastating landscapes all across the South, killing 500 people, and causing more than $1 trillion of damage in today’s dollars. Blues musicians throughout the region wrote songs about the tragedy, including Memphis Minnie (“When the Levee Breaks”), Bessie Smith (“Backwater Blues”), Barbecue Bob (“Mississippi Heavy Water Blues”), and Charley Patton (“High Water Everywhere”). That last song gave Dylan a title and some inspiration for Love and Theft‘s “High Water (For Charley Patton),” but it was really just a jumping-off point for a mythic ramble through 20th-century Americana that touches on Robert Johnson’s “Dust My Broom,” Big Joe Turner, the Ford Mustang, and the folk ballad “The Cuckoo.” (As the title of the album suggests, these songs contain both things he loved and things he stole.) That’s Larry Campbell on the banjo, anchoring the song even further in what Greil Marcus called the “old, weird America.” But only Dylan himself could deliver a line like “Jump into the wagon, love/Throw your panties overboard” and make it sound somehow profound. A.G.

Dylan sounded like he was singing from halfway into the grave on 1997’s Time Out of Mind, but he was, like, so much older then. The effortless feel of the playful-yet-ominous, hard-grooving, utterly dazzling “Things Have Changed” was an early indication of the renewed friskiness of Dylan’s 21st-century work — and the vividly live-in-the studio creations he would achieve as his own producer, with the help of engineer Chris Shaw. At the same time, with some influence from the midlife crisis depicted in Wonder Boys, the movie that inspired the song, he tosses off aperçus like his Sixties self (“You can’t win with a losing hand … all the truth in the world adds up to one big lie”). His purring, devastatingly timed delivery of lines like “Don’t get up, gentlemen/I’m only passing through” (borrowed from A Streetcar Named Desire) is a case all its own for Dylan as a great singer, even — especially — in his later years. The song won him an Oscar, which he would tote around onstage at every show to follow. B.H.