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    You are at:Home»Entertainment»Why the Bob Dylan/Willie Nelson Outlaw Festival Is 2025’s Must-See Tour
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    Why the Bob Dylan/Willie Nelson Outlaw Festival Is 2025’s Must-See Tour

    Earth & BeyondBy Earth & BeyondMay 25, 20250016 Mins Read
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    Why the Bob Dylan/Willie Nelson Outlaw Festival Is 2025’s Must-See Tour
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    Bob Dylan turns 84 today, and he will be spending the evening the way he might spend just about any random other night of the year: on a concert stage. There will likely be no commemoration of the occasion at the gig in Ridgefield, Washington, which will be just another evening on the Outlaw Music Festival 2025 tour he is once again sharing with Willie Nelson, with support from Billy Strings, Sierra Hull and some other Americana-favoring youngsters. Why would Dylan treat a birthday unlike any other night? True, we haven’t known him to actually play on Christmas, but he’d probably be out gigging on major holidays, too, if he thought a reasonable crowd would come out. It’s Willie who sings “I just can’t wait to get on the road again” (and there’s no reason to think he doesn’t mean it), but it’s Bob who most embodies that as his actual religion.

    Not that there’s any reason to look for daylight between these two giants and their touring philosophies. There is some kind of swim-or-die mentality that motivates Dylan and the 92-year-old Nelson to be out doing what they’re doing. Other octogenarian-and-up types might consider keeping at it to provide further annuities for their heirs, or because there’s no much thing as too much money, or because, like John Huston in “Chinatown,” they imagine they can buy the future — or because of narcissism. I could be wrong, but I don’t imagine any of these rationales really seriously figuring into why Nelson and Dylan are on the road again. It’s because they love it and because they’re still effing good… better, even, in some regards, if you can take the view that experience is a feature and not a flaw for artists who can maintain a real, ongoing vitality. Not to make this into some kind of AARP tract, but: Are there any figures in American music more inspirational than these two? It was true when they were still mere sprouts of, like, 64 ad 72, but all the more so now that they are seriously defying gravity.

    Last weekend, they played the Hollywood Bowl, and if you’re in L.A., maybe you were tempted to skip it — maybe you in fact did — because they’d just done it the year before. What a foolish notion that would have been, or was, depending on where you chose to spend your Friday night. There’s an obvious reason to hit these festival tour stops, which is that people who are pushing the envelope of high performance levels in entertainment cannot do it indefinitely, or so we’ve been assured, before health issues inevitably have their day. But I’d say that “this could be the last time” is only the third- or fourth-best reason to catch this tour (if, sure, a compelling one). The overriding one is that these would count as terrific performances even if we could be assured that they’ll still be out there pulling off similar feats five or 10 or 15 years from now. They are embracing the spirit of each night’s moment in an accomplished and downright frisky way that most younger achievers can only aspire toward (although, to give credit where it’s due, most of the younger acts they’ve picked as openers seem like the types who could absorb these lessons).

    And, maybe most significantly: If you live in a city the Outlaw Festival is visiting, the best way to think of it is having half of a living Mount Rushmore coming to you. (I’m not even sure who counts as the other half, at this point; perhaps we can just carve the two of them into the mountain twice.)

    There is certainly a lot of commonality to Nelson’s and Dylan’s appeal and performing styles — that loose sense of ragged but right that makes the “outlaw” tag for the tour feel like it’s not completely a branding conceit. Greil Marcus once wrote a book about “the old, weird America” focused on Dylan, and Nelson ought to fit into that, too, as one of our seminal dusty beat poets, even if his appeal is so broad and his persona so warm that his music is welcome in practically every home in the United States.

    But at the Bowl, it was quickly apparent what separates these two icons in live performance. To cite the most basic difference, no one is going to play a guessing game in advance of the tour of whether any hits will make it into Nelson’s setlist; What Would Willie Do is a fairly answerable question, from one year to the next. His show is a clear and present crowd-pleaser, which makes it obvious why he closes the bill each night, however equally yoked they might otherwise be. You will also know it when he has played your favorite song of his, as opposed to the long-standing joke about Dylan, that you might only realize he actually did dig into the hits from hearing people talk about it on the shuttle bus back.

    Willie Nelson in concert on the Outlaw Music Festival tour
    Stevo Rood / Live Nation-Hewitt Silva

    This is not to say, though, that Nelson curates a rote hits list. One of the great joys of his set in recent years has been his inclusion of a song the plurality of fans probably wouldn’t miss if he excluded it, the 1993 track “Still Is Still Moving to Me,” which is arguably one of his very best — and possibly the one that best represents the Zen-ness we have long associated with his laid-back yet quietly driven persona. Belying the title, it’s one of the fastest songs Nelson does in his show, and from all indications, it might be the one he most enjoys playing guitar on. The still-waters-run-deep tune is a chance for him to really re-prove his chops each night, soloing in a different style than the trademark licks he brings out for his slower and more familiar classics. Watching him dig his fingertips into those strings in such fleet fashion at 92 feels like a small miracle, even more than the surprising intactness of his tenor.

    The most variable parts of a Nelson set usually have to do with the “…and Family” part of the billing for his show. In some recent years, he’s been seated between sons Lukas and Micah (who performs under the stage name Particle Kid). This year, Lukas is out and someone who almost feels as much like a son as either of them, Waylon Payne, is taking the stage-right chair, quite commandingly when it’s his turn to shine. The senior Nelson of course gets a bit of a breather when one of these other two singers takes over the lead, but that aspect also adds a fun variety-show feel without it feeling like you’re getting any less time with Willie. “Waylon, play that song your mom had a big hit on,” and country fans will of course know that’s an intro for Payne’s full-throated rendition of “Help Me Make It Through the Night,” the Kristofferson classic first popularized by his mother, Sammi Smith. Micah Nelson, for his part, has no trouble winning over the crowd with a less familiar original, “Everything Is Bullshit.” You pretty much can’t lose an audience with a title like that, but at the Bowl, Micah’s dad really helped sell it, by chiming in on background vocals and just kind of scatting around with the word “bullshit,” like a profane jazz singer.

    There are sad and bittersweet songs in Nelson’s setlist, of course — “Angel Flying Too Close to the Ground” being another showcase for his utterly undiminished acoustic guitar playing as well as the tender sentiment. But light-heartedness is what you leave his show with, even when he’s singing about mortality. Maybe especially when he’s singing about mortality. Willie threads a good deal of death-consciousness through the second half of his show, and makes it all feel like we’re going to go out under the influence of laughing gas. In that final stretch, going from his cover of Tom Waits’ poetic “Last Leaf on the Tree” to the strictly hilarious “Roll Me Up and Smoke Me When I Die” and “Still Not Dead” to the spirituals “I Thought About You, Lord” and “Will the Circle Be Unbroken/I’ll Fly Away” (with “I Saw the Light” as his exit music). That’s a hell of a heavenly needle to thread.

    Has anyone done it this well, this far into a career? Surely there are less famous example of performers in this or related idioms who’ve still been rocking it this effectively into their 90s… but it’s hard to think of any at the moment, so let’s just say no. And say yes to embracing the mystery of why his hands and voice have been thus blessed.

    Willie Nelson in concert on the Outlaw Music Festival tour
    Stevo Rood / Live Nation-Hewitt Silva

    By Willie’s standard, Dylan counts as a spring chicken, still. He’s as playful as one, anyhow. Of course, you will not get a good look at him. Dylan has been famously resistant going back years and decades to having his performances turned into live concert movies, which might shatter the kind of earthy mystery he exults in maintaining. During the first part of his Hollywood Bowl show, there was no videography at all. Then a shot of the band finally came onto the screen midway through, and the audience cheered, as if they were finally going to see him in closeup at last. Far from it; the rest of the show just had one single long-shot of him and his band, taken from a distance. It basically allowed those in the very back of the Bowl to see the kind of view they’d get if they were sitting only halfway back. You can find that kind of annoying, or kind of appropriate and hilarious, given the unconventional figure we’re dealing with.

    Actually, maybe that’s a choice that seems apparent to a lot of attendees during a Dylan show. He never caters his setlists toward fair-weather fans — and although you’d think maybe he’d be more inclined to make things more audience-friendly at an Outlaw Music Festival gig, where the crowd is not necessarily all there because they’re way into him, the opposite could just as well be true. You could imagine he feels less fealty to the idea of having to be a crowd-pleaser when he knows that he is not the climax of the evening, and that Willie will send everyone home happy regardless.

    But, with all that said, here’s the thing: His 2025 festival set does feel oddly more like something that delivers clear audience gratification than any show he’s done in years. And that’s even with it having a fair share of oddball cover choices that seem unfamiliar even to a lot of pretty hardcore music buffs. It’s something that feels more intuitive than looking at his setlist and breaking it down along binary “classics/obscurities” lines. At the Hollywood Bowl show, at least, he actually established some rapport with the audience (now there’s an “obscurity,” as these things go). While he hardly ever sang anything in a way that aped the recorded version, his phrasing was as clear as it’s been in years, if not decades. And the rearrangements of the oldies didn’t feel arbitrary; sometimes, they almost made the classic songs feel more accessible. Go figure, and go enjoy.

    Dylan has often been known to not say a word on stage, which casual comers will sometimes mistake for disinterest. He wasn’t exactly a motormouth at the Bowl — we are never going to get a return to the evangelical preaching years, for better or worse — but if you’re a Dylan buff, you probably had a couple of LOL moments at what he did say. Like: “What are you eatin’ out there?,” which probably every artist who has ever played the Bowl has wondered, peering out at the chow-happy boxholders. Later on, he did band intros — also far from a given at Dylan shows — and described guitarist Doug Lancio as “one of those guys that went down to the crossroads — Doug made a deal with the devil just to play his guitar. I know you can tell. Ain’t that right, Doug?” (The rest of his current combo consists of Bob Britt and Tony Garnier, who like Lancio have been with Dylan for a while now, and drummer Anton Fig, who just recently stepped in to replace Jim Keltner.)

    As fans will know, it’s been many years now since Dylan switched over from playing guitar to piano (with very rare exceptions). And no one is going to make the same claim to greatness for his piano soloing that it’s easy to make for Willie’s guitar soloing. But given that the whole band is encouraged to adopt an improvisational feel, his kind of loose brutalism as a keyboard player feels in line with what the rest of the ensemble is up to, and occasionally is something more precise and beautiful than that. His voice, anyway, is perfectly lovely, in its perfectly imperfect fashion. Some observers continue to wonder if Dylan is reaping the benefits of quitting smoking, or has some other more talismanic explanation for why he is sounding so strong. What’s clear is that he wants to communicate these songs, in his own treat-’em-like-jazz way. “I used to care, but things have changed,” he sang in the set’s Oscar-winning opening number — and less true words were never spoken, because you don’t get at a performance this enchanting carelessly.

    Dylan has been bringing out some highly unexpected cover choices since the Outlaw Festival kicked up earlier this month: the Charlie Rich country hit “I’ll Make It All Up to You,” Bobby “Blue” Bland’s “Share Your Love With Me,” George Butler’s “Axe and the Wind.” (One audience gott the bonus of Rick Nelson’s “Garden Party,” which would have been appropriate for the Hollywood Bowl and its primo “garden” seats, but didn’t make it in that night; others have heard him break out “Route 66” or a Pogues song.) These are treats, representing the passion of a musical omnivore who probably has 10,000 songs he’d like to hep us to. But they’re confections sprinkled into the original classics he’s doing justice to on this tour.

    “Love Sick” sounds just as you remember it — he’s not perverse enough to want to drastically change up every number. But the ways in which he transformed some of the other staples of his catalog was delightful, for those of us who don’t reflexively find any alteration dismaying. “All Along the Watchtower” picked up a few more chordal variations than the original, with a switch to major chords during the choruses that afforded the song some surprises, and pleasantly so. With Dylan’s piano temporarily taking a back seat, “Watchtower” also had the band alternating electric and acoustic guitar solos, while “It Takes a Lot to Laugh It Takes a Train to Cry” allowed for a bit of an electric guitar duel. On “Desolation Row,” though, Dylan’s piano became the lead instrument again, over a light rockabilly rhythm that made the song feel like something Johnny Cash really ought to have covered. And “Blind Willie McTell” had a descending chord pattern that proved perfectly fitting for its piano-and-standup-bass setting.

    This is how Dylan reverses the years: by being playful with his own material, and others’. If, in past years, fans would sometimes argue he was doing that to the point of not treating his catalog respectfully, whether or not that was a valid criticism, I don’t think anyone will be saying that about the performances on the Outlaw Music Festival outing. He’s found a truly sweet spot between a constant sense of adventure in the music and the clear sense that he’s mixing things up a little because he loves these songs, not because he’s weary of them. It’s an ideal attitude with which to go into year 85.

    If presidents Washington, Lincoln, Jefferson and Roosevelt could talk, I think they’d tell you to seek out Dylan and Nelson in concert, too — don’t wait for the sculpting when you’ve got them in the flesh.

    The remaining Outlaw Music Festival tour dates and supporting lineups:

    May 24, 2025
    Cascades Amphitheater, Ridgefield, WA
    Willie Nelson & Family
    Bob Dylan
    Billy Strings
    Lake Street Dive
    Sierra Hull
    Lily Meola

    May 25, 2025
    The Gorge Amphitheatre, Quincy, WA
    Willie Nelson & Family
    Bob Dylan
    Billy Strings
    Lake Street Dive
    Sierra Hull
    Lily Meola

    June 20, 2025
    Pine Knob Music Theatre, Clarkston, MI
    Willie Nelson & Family
    Bob Dylan
    Nathaniel Rateliff & The Night Sweats
    Trampled by Turtles
    Myron Elkins

    June 21, 2025
    Blossom Music Center, Cuyahoga Falls, OH
    Willie Nelson & Family
    Bob Dylan
    Nathaniel Rateliff & The Night Sweats
    Bruce Hornsby & The Noisemakers
    Myron Elkins

    June 22, 2025
    Riverbend Music Center, Cincinnati, OH
    Willie Nelson & Family
    Bob Dylan
    Nathaniel Rateliff & The Night Sweats
    Trampled by Turtles
    Myron Elkins

    June 25, 2025
    FirstBank Amphitheater, Franklin, TN
    Willie Nelson & Family
    Bob Dylan
    Nathaniel Rateliff & The Night Sweats
    Trampled by Turtles
    Tami Neilson

    June 27, 2025
    Radians Amphitheater, Memphis, TN
    Willie Nelson & Family
    Bob Dylan
    Nathaniel Rateliff & The Night Sweats
    Trampled by Turtles
    Tami Neilson

    June 28, 2025
    Hollywood Casino Amphitheatre, Maryland Heights, MO
    Willie Nelson & Family
    Bob Dylan
    Nathaniel Rateliff & The Night Sweats
    Trampled by Turtles
    Tami Neilson

    June 29, 2025
    Thunder Ridge Nature Arena Ridgedale, MO
    Willie Nelson & Family
    Bob Dylan
    Nathaniel Rateliff & The Night Sweats
    Trampled by Turtles
    Tami Neilson

    July 5, 2025
    Dos Equis Pavilion, Dallas, TX
    Willie Nelson & Family
    Bob Dylan
    The Avett Brothers
    The Mavericks
    Tami Neilson

    July 6, 2025
    The Cynthia Woods Mitchell Pavilion Presented By Huntsman, The Woodlands, TX
    Willie Nelson & Family
    Bob Dylan
    The Avett Brothers
    The Mavericks
    Tami Neilson

    July 25, 2025
    Ameris Bank Amphitheatre, Alpharetta, GA
    Willie Nelson & Family
    Bob Dylan
    Turnpike Troubadours
    Charles Wesley Godwin
    Willow Avalon

    July 26, 2025
    PNC Music Pavilion, Charlotte, NC
    Willie Nelson & Family
    Bob Dylan
    Turnpike Troubadours
    Charles Wesley Godwin
    Willow Avalon

    July 27, 2025
    Coastal Credit Union Music Park, Raleigh, NC
    Willie Nelson & Family
    Bob Dylan
    Turnpike Troubadours
    Charles Wesley Godwin
    Willow Avalon

    July 29, 2025
    Veterans United Home Loans Amphitheater, Virginia Beach, VA
    Willie Nelson & Family
    Bob Dylan
    Turnpike Troubadours
    Willow Avalon

    August 1, 2025
    Northwell at Jones Beach Theater, Wantagh, NY
    Willie Nelson & Family
    Bob Dylan
    Wilco
    Lucinda Williams
    Waylon Payne

    August 2, 2025
    Broadview Stage at SPAC, Saratoga Springs, NY
    Willie Nelson & Family
    Bob Dylan
    Wilco
    Lucinda Williams
    Waylon Payne

    August 3, 2025
    BankNH Pavilion, Gilford, NH
    Willie Nelson & Family
    Bob Dylan
    Wilco
    Lucinda Williams
    Waylon Payne

    August 8, 2025
    Darien Lake Amphitheater, Buffalo, NY
    Willie Nelson & Family
    Bob Dylan
    Turnpike Troubadours
    The Red Clay Strays
    Waylon Payne

    August 9, 2025
    Hersheypark Stadium, Hershey, PA
    Willie Nelson & Family
    Bob Dylan
    Turnpike Troubadours
    The Red Clay Strays
    Waylon Payne

    August 10, 2025
    Empower Federal Credit Union Amphitheater at Lakeview, Syracuse, NY
    Willie Nelson & Family
    Bob Dylan
    Turnpike Troubadours
    The Red Clay Strays
    Waylon Payne

    September 5, 2025
    Maine Savings Amphitheater, Bangor, ME
    Willie Nelson & Family
    Bob Dylan
    Sheryl Crow
    Waxahatchee
    Madeline Edwards

    September 6, 2025
    Xfinity Theatre, Hartford, CT
    Willie Nelson & Family
    Bob Dylan
    Sheryl Crow
    Waxahatchee
    Madeline Edwards

    September 7, 2025
    Xfinity Center, Mansfield, MA
    Willie Nelson & Family
    Bob Dylan
    TBA
    Waxahatchee
    Madeline Edwards

    September 12, 2025
    Freedom Mortgage Pavilion, Camden, NJ
    Willie Nelson & Family
    Bob Dylan
    Sheryl Crow
    Waxahatchee
    Madeline Edwards

    September 13, 2025
    PNC Bank Arts Center, Holmdel, NJ
    Willie Nelson & Family
    Bob Dylan
    Sheryl Crow
    Waxahatchee
    Madeline Edwards

    September 14, 2025
    Merriweather Post Pavilion, Columbia, MD
    Willie Nelson & Family
    Bob Dylan
    Sheryl Crow
    Madeline Edwards

    September 19, 2025
    Alpine Valley Music Theatre, East Troy, WI
    Willie Nelson & Family
    Bob Dylan
    Sheryl Crow
    Waxahatchee
    Madeline Edwards

    2025s Bob DylanWillie Festival MustSee Nelson Outlaw Tour
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