On his most recent album of original material, released five and a half years ago now, Bob Dylan sings (or croaks) a lyric that seems profoundly self-referential: “I’ve already outlived my life by far.” Like all things Dylan, it is open to interpretation. Here’s mine, specially tailored for what I’m about to write: Bob Dylan believes he has outgrown the clichés that people use to talk about him.
Anyone casually conversant with classic-rock history can recite them by heart: He’s a wild card. His entire artistic project is predicated on doing the opposite of what’s expected. Who knows what he’ll do next? Nobody, that’s who. That’s the Bob Dylan we think we know. The guy preoccupied with keeping the public on edge, on shocking us, on being the provocateur. Going electric to piss off the folkies, playing redneck country music to confound the anti-war hippies, converting to Christianity at the end of the “Me Decade” 1970s to bum out the proto-yuppies, appearing in a Victoria’s Secret commercial to disappoint sex-negative anti-capitalists, and so on.
But what if Bob Dylan isn’t that person anymore? What if, like the song says, he has already outlived that life by far? What now? In 2025, the answer to that is the opposite of doing the opposite of what people anticipate. It is being the most predictable version of Bob Dylan that Bob Dylan can possibly be. That is the new contrarianism. The final frontier for rock’s poet laureate. For now, anyway. (But maybe for good.)
I’ll explain: In September 2021, Bob Dylan announced a new round of shows, his first since the COVID shutdown. Up through 2019, he was famously (if unofficially) engaged in the so-called “Never Ending Tour,” a series of annual concert runs going back to 1988. Every year, he played dozens of gigs, sometimes more than 100, all over the world, mostly in towns you’ve never heard of. And he performed god-knows-how-many-songs: rock ’n’ roll songs, folk songs, blues songs, country songs, gospel songs, songs by everybody from Warren Zevon to the Clash to Tom Petty (once, after he died in 2017), and, naturally, selections—including some of his biggest hits—from his own voluminous catalog.
Fans assumed this new tour would be more of the same. But it didn’t turn out that way. And it should be noted that Bob never said it would be. In fact, he made sure to explicitly point out that this tour wasn’t “never-ending.” He indicated—in every press release, poster, and flyer circulated to promote the tour—that it would last precisely from 2021 to 2024, practically the length of a presidential term. He even gave the campaign a specific name: The Rough and Rowdy Ways World Tour, named after the elegiac record he put out in June 2020.
In retrospect, it’s funny how direct he was about what these shows would be. From the beginning, he was committed to the core concept, which was performing material from his most current record. At every show, he played the same songs, usually in the same order. The set list covered nearly all of Rough and Rowdy Ways, plus a static selection of tunes from his back pages (including “Watching the River Flow,” “To Be Alone With You,” “I’ll Be Your Baby Tonight,” and “Every Grain of Sand”) that managed to be both largely unknown to casual fans and overly familiar to anyone following Dylan’s recent live activity during the “Never Ending Tour” era.
As 2021 turned to 2022, and then 2022 became 2023, the shows unfolded with stunning uniformity. Occasionally, he might insert a cover specific to where he was playing that night. (He did “Kansas City” in Kansas City and “Born in Chicago” in Chicago.) In 2024, he started opening concerts with “All Along the Watchtower,” his most played song ever, though in this context it felt like a Bootleg Series obscurity.
Other than that, it’s remained unchanged—night after night, leg after leg, year after year. And yet some of his followers still can’t let go of the old routines. During a concert in Fort Lauderdale last year, an exasperated woman in the audience demanded Bob to “play something we know!” I know what she meant, but it was still odd: At no point in Dylan’s career has it ever been easier to guess which song he will play at any moment. (The heckler interjected right before “When I Paint My Masterpiece,” the fifth song of the night, just as it was the show before and the show after.) Nevertheless, the press attempted to spin the incident as a geriatric update of the historic “Judas!” moment from nearly 60 years prior, claiming that Bob defiantly played a weird, impromptu arrangement of the song based on Irving Berlin’s “Puttin’ on the Ritz.” (In reality—this is even weirder, admittedly—Bob had already planned to make that arrangement part of the regular show.)
In 2024, Bob announced he was joining Willie Nelson’s yearly Outlaw Tour revue for 25 dates that summer. Like that, the set list suddenly changed. The Rough and Rowdy Ways songs disappeared. He was back to playing a mix of rock ’n’ roll, blues, and country numbers. He even revisited old favorites like “A Hard Rain’s A-Gonna Fall” and “Ballad of a Thin Man.” Many assumed this signaled a return to “Never Ending Tour”–style concerts. But when Bob got back to his own tour that fall, the set list just as swiftly reverted to the Rough and Rowdy Ways mean. And then, despite his original promise, this continued into 2025. Then, last month, Bob went on X and promised “fans and followers of [the] Rough and Rowdy Ways Show” that it would be back, yet again, in spring 2026. He followed through this week, announcing 27 more shows in places like Omaha, Nebraska; La Crosse, Wisconsin; Bowling Green, Kentucky; and Dothan, Alabama.
In all, there have been 276 Rough and Rowdy shows so far. That’s 276 live versions of almost every song from the album, save for “Crossing the Rubicon” (played “only” 255 times) and “Murder Most Foul” (the hallucinatory 17-minute track about the JFK assassination that, to date, has never been attempted on stage). This is remarkable for at least three reasons. One, Bob will be 85 years old in May, and there’s no sign he’s winding down his tour schedule. Two, no artist of his generation has ever committed this hard to playing his latest material. (The “bathroom break” rule for late-career work by beloved legends continues to rule at most shows.) Three—I can’t say this with absolute certainty but I’m 99 percent confident in the statement’s veracity—no artist of any generation has toured behind an album for this long. Metallica played about 250 shows over 21 months for the Wherever We May Roam tour in support of "The Black Album," but those look like rookie numbers now in comparison. Also: “The Black Album” is one of the best-selling albums of the SoundScan era. Rough and Rowdy Ways, meanwhile, is not.
This is, unquestionably, the strangest, most singular and all-around extraordinary ongoing tour of the decade. The inverse of the Eras Tour, as narrow in terms of repertoire as the 2020s’ most profitable tour was wide. Which prompts the most clichéd Bob Dylan question of all: What does any of this mean?
Bob Dylan performs as a surprise guest during Farm Aid
Ray Padgett is the only person I know who cares about any of this more than I do. We’re both part of the “Dylan acolyte” content creation economy, which isn’t Swiftie-level robust in 2025 but still fairly strong. I’m the cohost of a medium-popular podcast loosely focused on the Never Ending Tour, and he’s the writer of the definitive Substack newsletter about Dylan’s live career. (Here’s a more nerd-friendly rubric for measuring our respective qualifications: I’ve seen five Rough and Rowdy Ways–era concerts, and he’s been to 21.)
Like all Dylan devotees, we’re both fixated on the fragility of our hero’s continued existence. It’s a topic that never fully leaves the front of my mind. At least once per day, I think about what it will be like when he dies. (Which is not something I do for my own mother, only for Bob.) I imagine how I’ll receive the news (on my stupid phone, inevitably), how I’ll take it (not well), and what I’ll write as a tribute (nothing worth previewing here). All this makes me especially grateful that he is still around, and that he is still touring, and that he continues to do things I don’t understand.
Having said that: Isn’t this tour just a touch … frustrating? We are talking, after all, about the greatest songwriter in the world. He has so many good songs! And we hear so few of them now. Or is complaining about this, even a little bit, the behavior of an ingrate? Should I just be delighted by the whims of music’s most active octogenarian?
“Can I be delighted and frustrated?” Ray counters. “It’s a piece of performance art as much as it is a concert at this point.”
A lot of things Bob Dylan has done in the 2020s could also be classified as “performance art.” Particularly his social media activity, which includes sending birthday wishes to the Russian composer Dmitri Shostakovich and the magician Ricky Jay (both long dead) on X, dabbling in AI-created audio clips of 1930s gangster Al Capone on Instagram, and stanning for Machine Gun Kelly to the confusion of everyone, including Machine Gun Kelly.
Bob’s posts have generated at least as much media attention from mainstream outlets as the Rough and Rowdy Ways Tour. Meanwhile, Ray has covered the shows like how The New York Times tracks a foreign war, posting reams of recaps from deputized Bobcats from around the globe while noting the (not always) minuscule changes to the songs’ arrangements. Because every concert Bob Dylan performs is recorded surreptitiously by fans and then disseminated online within a few days via message boards and other clandestine channels, each note can be analyzed and dissected in search of potential brilliance.
Herein lies the appeal for Dylan freaks like Ray and me: Bob is playing the same songs, but he is not playing them the same way. Tempos speed up, and then they slow down. (This may or may not be related to Bob cycling through four different drummers in the past four years.) Certain licks or riffs played by one of the two guitarists in his band—or Bob himself on piano—will materialize, and they might stick around for a specific leg or even for a few years.
Can I be delighted and frustrated? It’s a piece of performance art as much as it is a concert at this point.Ray Padgett
Dylan is notorious for remaking his songs beyond recognition, but the sameness of his modern set lists has upped the ante among diehards for close listening to his live recordings. The smallest of vocal utterances, the slightest shifts in rhythm, the most minute flashes of instrumental novelty—they all take on outsized significance when the overall structure scarcely changes.
I get why this is interesting. I am interested in it. The amount of time I spend listening to Dylan bootlegs is borderline irresponsible given that I make my living (mostly) by writing and talking about non–Bob Dylan music. But I’m also reminded of a Jeff Tweedy quote from a 2014 Esquire article where he talks about touring with Dylan, and the strangeness of watching Bob’s audience watch Bob. “If you dropped people out of a vacuum from another planet and planted them in a field somewhere so that they could study us,” Tweedy surmised, “and there's a guy half-decipherably singing jump-blues songs almost in the dark, and there's people watching him—well, it wouldn't make any sense."
And that was years before the Rough and Rowdy Ways tour. Attempting to explain to a normal person on this planet why the 123rd live version of “Goodbye Jimmy Reed” is meaningfully different from the 207th is a tall task indeed. Even some hardcore fans have trouble with that one. “I was at opening night in Milwaukee. And it was incredible,” says Andy Greene, a veteran music journalist who covered the first show of the Rough and Rowdy Ways tour for Rolling Stone. “One of the best Dylan shows I’ve ever seen. But I had no inkling it would still be going in 2026.”
Greene started attending Dylan shows in the late ’90s and early ’00s, now widely regarded as one of his finest live eras, when his far-reaching repertoire and well-versed backing musicians invited Deadhead-like devotion among the faithful. When Bob transitioned to the Outlaw Tour, “I thought, ‘We’re free now,’” Greene says. “And then boom! He goes right back to it.”
The Outlaw Tour shows, which were revived in 2025 in parallel with the Rough and Rowdy Ways dates, have presented a Faustian bargain to stalwarts. My favorite Bob show of the 2020s was an Outlaw Tour concert from September 2024, when I got choked up during a gorgeous cover of the Grateful Dead’s “Stella Blue” under a perfectly starry early autumn night sky. But while the set lists have greater breadth, the Outlaw Tour audiences care way more about Willie than Bob, which means Dylan’s sets are typically drowned out by semi-stoned chatter. And then there’s Bob’s churlish attitude about phone cameras—he bans them outright at Rough and Rowdy Ways shows, while on the Outlaw Tour he tends to either hide behind his enormous piano or obscure himself in darkness. (I “saw” him at Farm Aid in Minneapolis this fall, where he was essentially a black hole on a Jumbotron screen.)
I shared a theory with Greene about how the Rough and Rowdy Ways Tour has evolved into a kind of theater piece, akin to a Broadway musical, that Bob opts to revive each year. (Hence the strange wording of that tweet referring to fans of the Rough and Rowdy Show, rather than fans of Bob Dylan.) Doing the Outlaw Tour has unwittingly extended that run, I proposed, by giving him a respite from performing those songs for a few months, at which point he’s refreshed and ready for more. (Some oldies from the Outlaw Tour, including “Desolation Row” and “It’s All Over Now, Baby Blue,” have carried over to Rough and Rowdy Ways.) But Greene couldn’t help hearkening to the “real golden age” of the Never Ending Tour. Even the Outlaw Tour set lists are mostly the same every show. But back then, “there were often real surprises. And that was part of the joy of it. And I miss that.”
Of course, as Bob himself would likely point out, there were exasperated people at those concerts, too, the ones who also yelled for him to “play something we know.” Complaints about Bob Dylan not doing what he used to do are as unchanging as Bob’s set lists are now. That’s one cliché we as fans have not outlived by far.
Bob Dylan performs at Hyde Park in London
When I phoned Ray, I forgot to bring up the most mysterious figure lurking in the background of the Rough and Rowdy Ways era: “the cowboy,” allegedly working as Dylan’s personal assistant. I first heard about “the cowboy” in 2023, when I interviewed Big Thief guitarist Buck Meek and asked about his experience working on Shadow Kingdom, a live-in-the-studio reworking of old songs that Dylan originally presented as a pre-tour pay-per-view concert film in July 2021.
“Well, I’d love to talk about it,” Meek replied, “but I swore to a very intimidating cowboy that I wouldn’t speak a word of the matter. My apology.”
Talk about performance art. I laughed, assuming he was speaking euphemistically. “A very intimidating cowboy,” clearly, meant “a non-disclosure agreement” or, less ominously, “ostracization from future Dylan projects.” But Meek insisted he meant a literal cowboy, “with boots, and a belt buckle, and a big-ass knife.”
I laughed again, this time awkwardly. Feeling a little mystified, I decided to change the subject. Then, this past July, I read an interview on Ray’s Substack with accordionist Alexander Burke, who also interacted with this enigmatic cowboy during Shadow Kingdom. “Jeans, cowboy boots, white shirt. He sounded like he was from the South,” Burke insisted. “Every day before filming, he would come up and be like, ‘I got a friend coming. You might recognize him, you might not, but there’s a few rules. You can’t talk about the past, how much you love any of his art that you might know about, and you can’t talk about the future, what he’s planning on doing. You can only talk about the present. Nothing about the present is off limits, but you’re not allowed to talk about the past or the future.’”
What does any of this mean? For one thing, it suggests that Bob Dylan doesn’t follow his own rules regarding not talking about the past. The announcement of Rough and Rowdy Ways was preceded in the spring of 2020 by a pair of singles, “Murder Most Foul” and “I Contain Multitudes.” Both tracks signaled a songwriting tic that recurs on the album, which is a tendency to just list the names of famous people—politicians, musicians, writers, composers, movie stars—in a hypnotic cadence. In “I Contain Multitudes,” he likens himself, hilariously, to Anne Frank, Indiana Jones, and “them British bad boys the Rolling Stones.” The epic set piece “Murder Most Foul” starts off as a “death of boomer innocence” ode, like a bizzarro-world twist on Don McLean’s “American Pie,” and then shifts to a mesmerizing series of pop-culture shout-outs that goes on for several minutes, like a malfunctioning streaming platform on endless shuffle: Billy Joel, Etta James, Guitar Slim, Glenn Frey and Don Henley, Queen, Charlie Parker, Stan Getz, Buster Keaton, Terry Malloy, Howard Hawks, Dickey Betts, Shakespeare, Stevie Nicks and Lindsey Buckingham, Jelly Roll Morton, “the great Bud Powell”—the luminaries, some still remembered and others largely forgotten, stretch on and on.
There were often real surprises. And that was part of the joy of it. And I miss that.Andy Greene, on the golden age of the Never Ending Tour
On the record, Bob continues his list-making ways on the gently drifting road song “Key West (Philosopher Pirate),” my favorite Rough and Rowdy Ways track. He speaks of writers (Allen Ginsberg, Gregory Corso, Jack Kerouac), American presidents (William McKinley and Harry Truman), songs (Otis Redding’s “Try a Little Tenderness,” Bobby Darin’s “Beyond the Sea,” Joe South’s “Down in the Boondocks,” the blues standard “Goin’ Down Slow”), and fanciful realms (the land of Oz). He alludes to “gumbo limbo rituals” and “all the Hindu rituals,” and ultimately concludes that “if you lost your mind, you’ll find it there” in South Florida. The music, as it is throughout the record, is sparse and crawling and ancient and dreamlike. It moves at 70 beats per minute, slow for a song but ideal for a senior citizen’s resting heart rate. Listening to it feels like breathing while aimlessly staring out a car window.
Whether by edict of “the cowboy” or some other secret omertà, not much is known about the making of Rough and Rowdy Ways. The songs apparently were written not long before they were recorded in the first two months of 2020, right under the COVID wire. But it’s fair to assume that this record means more to him than a regular Bob Dylan album. His rigorous commitment to playing the songs live, apparently, speaks to that. But there’s also the uncommon elegance of the original recordings, among the very finest of his 21st-century work. Notorious for treating his albums like hastily assembled rough drafts for songs he eventually works out on stage, Dylan brought extra care and tenderness to this music at its inception, which paradoxically makes it harder to replicate in concert.
Rough and Rowdy Ways is the rare Dylan album (the only Dylan album, in my estimation) where the studio versions are superior to any live performance. I’ve listened to countless concert recordings of “Key West,” in addition to the ones I saw in person, and most of them don’t work at all. That invisible, pulse-like rhythm has vexed his entire coterie of recent timekeepers, and this shaky inner core has caused most renditions to drift off that Florida highway and into the swamp. Whereas “Key West” on record floats effortlessly, it often comes across as flat-footed and tedious during Dylan’s nightly run-throughs.
This speaks to the central (and extremely Dylanesque) contradiction of the Rough and Rowdy Ways Tour—it’s a long-running show built on an album perhaps best suited to be experienced at home with a pair of nice headphones.
More on Bob Dylan
OK, for real this time: What does any of this mean?
If we fall back on the clichés, the answer is simple: mortality. Mortality is the most common noun used in Bob Dylan’s album reviews going back to the late ’90s. It started with 1997’s Grammy-winning Time Out of Mind, released not long after he was hospitalized for a near fatal fungal infection. Four years later, he put out Love and Theft, which music writers said evinced “a lyrical obsession with mortality.” On 2006’s Modern Times, reviewers noted a familiar sense of “encroaching mortality,” and on 2009’s Together Through Life, “the contemplation of mortality” encroached further, “creeping evermore perceptibly into Dylan’s verse.” Alas, by 2012’s Tempest, he was “still obsessed with mortality,” though perhaps not as much as his critics.
What, exactly, does “mortality” denote here? Bob Dylan, folk singer to the end, has devoted the majority of his life to excavating old and discarded artifacts—songs, traditions, cultures, entire worlds—that are inevitably swept back into the dustbin of history by the rest of us. He has always, in some way, situated himself in spaces that are in the process of being erased. When he was in his 20s, this was a conscious choice. But in his 80s, it’s an unavoidable circumstance of his age. The awareness of just how much has been lost and forgotten during his lifetime, I imagine, is overpowering. What can you do in response except insist on remembering every faded name, landmark, and signpost you can conjure, and then giving your testimony in whichever theater, arena, semi-pro hockey rink, or college basketball gym you are able to book, while you can, for as long as you can?
In addition to those reference-heavy Rough and Rowdy Ways songs, the philosophical bent of the show’s older numbers is clear. Two of the staunchest mainstays, “When I Paint My Masterpiece” and “Watching the River Flow,” are his most direct statements about how fickle and ephemeral the artistic process can be. Just as the nightly closer, “Every Grain of Sand,” is a prayer acknowledging man’s insignificance in relation to the universe.
And then there’s “To Be Alone With You,” which seems to have no deeper meaning other than that it comes from 1969’s Nashville Skyline, a B-tier Dylan record typically overshadowed by his more famous music from the 1960s. Except Dylan now plays that song more than “Like a Rolling Stone” or “Blowin’ in the Wind” (neither performed live since 2019) or even “Knockin’ on Heaven’s Door,” his most popular track on Spotify, which hasn’t been dusted off by Bob in concert since 2003. But those songs don’t need an advocate like some of the others.
Bob also pays close attention to overlooked music by other artists, particularly their late career “bathroom break” records. On the Rough and Rowdy Ways Tour, he has covered songs from such albums by Bob Weir (“Only a River,” from 2016’s Blue Mountain), John Mellencamp (“Longest Days,” from 2006’s Life, Death, Love & Freedom), Merle Haggard (“Bad Actor,” from 2010’s I Am What I Am), and Van Morrison (“Going Down to Bangor,” from 2016’s Keep Me Singing). Insisting those songs matter, no matter the larger public’s indifference, reiterates the vitality of his own old-man music.
I can talk myself into believing that. But I have another theory about Bob Dylan that points me in a different direction: What if he is just an old guy from Minnesota? By which I mean, What if he’s a closet normie, and the guile and the calculation and the layers of meaning are merely projections coming from his audience’s overactive imagination? For example, he recently claimed that he wrote “Key West” while visiting Ernest Hemingway’s home there. It’s possible this trip inspired a Proustian reverie that sent Bob on an existential journey into self. But it’s also possible that he is just an old guy from Minnesota, the sort of person who likes to visit South Florida because he considers Jimmy Buffett one of the greatest songwriters of all time, so he wrote a song that Jimmy Buffett might have done if he had Bob Dylan’s audience.
Here's another example: In 2020, one week before the release of Rough and Rowdy Ways, Dylan granted an interview to The New York Times in which he laid out his approach to performance in the simplest terms: “You basically play the same thing time after time in the most perfect way you can.”
This statement is inexplicable on its face. “Perfect” is the last word anyone would ever use to describe any Dylan performance. In the same interview, he denied that improvisation is part of his process, because it “leaves you open to good and bad performances and the idea is to stay consistent.” This makes even less sense. “Consistent” might be the most egregious antonym of Dylan’s music imaginable.
“That’s bullshit,” was Ray’s response when I brought the interview up.
But if I apply the “just an old guy from Minnesota” lens, I can understand the difference between pursuing and achieving perfection. The desire for the latter necessitates the former. When you haven’t fully nailed down “Key West” yet, a solid Midwestern work ethic requires that you keep at it, even past the point of “normal” retirement age.
Over time, that pursuit becomes the point of it all. Grasping and grazing at the outer edges of some elusive “this.” All the while moving perpetually forward, with nothing but your wits and your wisdom and your Deadwood-looking guitar players and your lifetime bassist and the drummer your manager just hired. To paraphrase an old joke: How do you get to Dothan, Alabama? Practice. That’s the way you outlive your life by far—you just refuse to quit living.
