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The 25 Best Bob Dylan Songs of the 21st Century

In the years since 2000, Dylan has renewed his creative energy and produced a catalog of songs that stand alongside any past era of his career

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“Things should start to get interesting right about now,” Bob Dylan sang in “Mississippi,” and he wasn’t kidding. At the end of the 20th century, he was 58 years old, one of the most worshipped, most mythologized, most misunderstood artists alive, and far from finished. Over the next two decades, he’d change the very structure of his music, using more sophisticated chords than he’d ever attempted before, turning to jazz and the pre-rock standards he’d helped overthrow for inspiration, while finally finding peace with the recording process, which had vexed him for decades. He pushed the limits of his magpie ways, borrowing riffs and phrases both verbal and musical from every conceivable source, while (almost) always alchemizing them into something new. He could be vicious (“Pay in Blood”) or strikingly playful (“I Contain Multitudes”), revisiting the absurdist wit of his Basement Tapes-era writing, or digging into the blues with a mastery that shames even his Sixties high points in that vein. He’s 79 now, and his fantastic new album, Rough and Rowdy Ways, is his latest definitive proof that youth and inexperience are thoroughly overrated.

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“Key West (Philosopher Pirate)”

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.

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“Pay in Blood”

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.

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“Murder Most Foul”

“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.

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“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.



“Ain’t Talkin’”

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 TimesA.G.

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“High Water (For Charley Patton)”

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.

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“Things Have Changed”

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.