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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.



“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.