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.