Concert Review: Outlaw Fest 2025

As the night wore on at a nearly sold-out Alpine Valley Music Theater, I had one thought that kept coming back to me about the 10th Outlaw Festival. And that was that the name was a misnomer at this point. To me, “outlaw” suggests a bit of danger, and this show was anything but. It was overall too pleasant to be dangerous or daring. 

That isn’t exactly a ringing endorsement, but don’t get me wrong — Willie Nelson and Bob Dylan are true one-of-one American classics and this concert didn’t do anything to take that away from them. Waxahatchee and Sheryl Crow were also perfectly fine. I just found it funny that this is called Outlaw Fest, but any normie could come through the gates and enjoy themselves, even if they weren’t familiar with any of the music. 

All of that being said — I did enjoy the show. Read on for more in-depth thoughts, both positive and negative.

Waxahatchee and Sheryl Crow were the first two artists that I saw. I am going to lump them together here because I felt they are both pretty similar. They both deal in laid-back Americana, highlighted by excellent pedal steel in songs by each — “Right Back To It” by Waxahatchee and “Strong Enough” by Sheryl Crow. 

The vibes from each were wonderful; it felt like perfect festival music, if only the sun were out for their respective sets. 

Crow did differentiate her music via several bitchin’ guitar solos. “If It Makes You Happy” started a three-song run at the end of her set that got the crowd going, and it still absolutely slayed nearly 30 years on. It was mostly a greatest hits set, but that is not a thing to complain about. 

(If you’re unfamiliar with Waxahatchee, she and her band are awesome. Check out the aforementioned “Right Back to It” and also “Lilacs.” You will not be disappointed.)

Bob Dylan was next up, and he was Bob Dylan.

No one knows what the hell is going on here. Bob is supposedly there somewhere. 

Dylan doesn’t give a fuck what you want from him in concert, he has been doing his own thing since he went electric in 1965. 2025 Dylan isn’t any different. 

For an 84-year-old, particularly one not blessed with the best singing voice, Bob Dylan actually sounded pretty good. He has been working in the same old-timey blues-and-jazz arrangements for some time now, so to expect anything different was a fool’s errand. 

I recognized about half of his set, but almost none of them sounded like the versions on his albums. Dylanophiles will tell you this is what makes him great, casual fans will throw up their hands and want to never see him live again. I — unsurprisingly to some of you, I’m sure, — fall somewhere in the middle. I find some of his — shall we say… detours? — kind of annoying. But I respect what he does. The world needs more uncompromising artists, not less. 

Throughout his 75-minute set, I thought the arrangements were pretty simple in and of themselves. This allowed the crowd to get into the music even if it wasn’t recognizable immediately. There was, after all, plenty of dancing and swaying going on, which is not something I would expect at a Dylan show. 

“Early Roman Kings,” with its bedrock blues riff (think “Bad to the Bone”), was an early set standout. It was more guitar-driven compared to the album cut, which was pretty cool. 

“All Along the Watchtower” managed to channel Bob Seger or Jackson Browne at times, but was otherwise slightly disappointing. 

The epic “Desolation Row” seemed like it had a little pep in its step. Someone had a good harmonica run during it — was it Bob? Who the hell knows? The screens only showed a wide shot of the band, and never zoomed in on anything. Reports have suggested that Dylan has been making himself as unseen as possible this part of the tour. Apparently he was wearing a black hoodie with the hood up, so whatever I guess. 

It took to nearly the end of the set to get to a song that sounded mostly like the studio version, and that was for “Love Sick.” Good tune. Not much more to say than that.

The last couple of songs were a lesson in contrast. 

Neither sounded like the album cuts, because of course. But “Highway 61 Revisited” conjured up a sense of darkness or menace in its revision; “Don’t Think Twice, It’s Alright” fell completely flat. On album, it is a bitter kiss-off to a former lover; here the arrangement took the piss and vinegar out the song. It was toothless and noodling for no reason at all aside from Dylan wanting it to be that way. It reminded me of William Shatner’s take on “Rocket Man,” which is in no way a compliment.

Dylan may or may not have said “thank you” at any point during his set, and he also didn’t introduce the band, which is odd for even him. That’s just how it goes with Bob; take it or leave it.

Every time I go to see Willie Nelson, the same thoughts pop up: 1) Is this going to be sad? (As in — should he just hang it up already?) And 2) Will this be the last time?

I can answer question one with a Dylan lyric: It’s not dark yet, but it’s getting there. 

Willie Nelson can still play guitar pretty good, which is amazing for a 92-year-old-man. He did not play during every single song, which is perhaps for the better. I also felt his singing was a bit more behind the beat than usual — it might be his signature, but the way it has slipped was noticeable at times. 

But it is “Willie Nelson and Family,” and family — one man in particular — sure helped him out during the hourlong set. Waylon Payne, son of Jody, Willie’s former guitarist, sat in with Nelson throughout. He led “Working Man Blues” just like his old man, and backed Willie on both guitar and vocals on several cuts, including crowd-participation favorite “Mamas Don’t Let Your Babies Grow Up to Be Cowboys”

This all being said, Willie still commands all the attention. He may be performing mostly the same set since about 1978, but his age lends gravitas to the songs that make them still worth seeing live.

“Angel Flying Too Close to the Ground” was absolutely stunning. His voice might be diminished but the emotion was there in spades.

Mickey Raphael’s harmonica was excellent as always; I’ve felt that he has been the heart and soul of the band for some time now. But during “Last Leaf,” a Tom Waits cover (!), he ditched it for a longing accordion to great effect. The most poignant moment of the night came when Willie sang “If they cut down this tree / I’ll come back in a song.” This elicited a big cheer from the crowd, and rightfully so. 

If ever there was a mission statement for Willie Nelson for this moment in time, that was it. 

The set ended with traditional group-wide singalongs, “Will The Circle Be Unbroken” and “It’s Hard to be Humble.” The joy was palpable on stage — one hopes the crowd savored every moment because it could very well be the last opportunity to do so. 

Willie and his great?-granddaughter. 

Overall I would say Outlaw Fest 2025 was perfectly fine. Sitting in the lawn seats was certainly a different vibe. The constant talking and movement of the people honestly took me out of the show here and there. The $17 beers (and more, depending on what you wanted) were a bit much. But the performances themselves were are all good — even Dylan, who will be eternally confounding!— and I can’t really ask for more than that.