Outlaw Tour 2025 - Top 5 Moments
A Summer of Surprises, Experiments, and Moments That Reminded Us Why We Still Follow Bob Dylan.
There is a special kind of energy that follows Bob on a tour like this. The Outlaw Tour 2025 was not about big effects but about surprises and changes. Songs moved around in the set, old favorites returned, a guest came on stage, and one classic song was played for the first time in fifteen years.
What follows is not a list of every show. It is a countdown of the five moments that truly stood out. These were the nights that made us fans talk, share, and even jump on planes at the last minute. Dates and places matter, but what matters most is how these moments felt.
We at Daily Dylan tried our best to keep you up to date at these four legs, so here they are, our Top 5 Moments of Outlaw Tour 2025!
5. “Positively 4th Street” Returns After 12 Years!
No one really expected Bob to pull “Positively 4th Street” back into the rotation this summer. He slipped it into Alpharetta as song 14, then kept it at slot 15 in Charlotte and Raleigh. After a brief disappearance, the song resurfaced dramatically as the opener in Saratoga Springs on August 2 (being the opener for the first time since 1989), then opened again in Gilford the day after. One show later it was back in the middle of the set, appearing as song 14 after a very different opener. The mini-arc felt like watching Bob test a mood, reshape it, and try it in different places until it clicked.
Yesterday we kicked off our collaboration with Carol Casper by sharing an exclusive, previously unreleased “Positvively 4th Street” video in yesterday’s newsletter. If you missed it, you can check it out, here!
The reason for its short-lived stay became clear in Buffalo! (see 4th place)
4. “Masters of War” Returns
Beginning in Buffalo on August 8, Bob suddenly opened with “Masters of War” for the first time since he’d played the song at all back in 2016—and for the first time since 1963 as an opener. He kept it in the pole position for the rest of the tour. Hearing that riff and those words as the very first thing changed the temperature in the venue and reframed everything that followed.
3. Billy Strings joins Bob for “All Along the Watchtower”
Bob does not invite many guests these days. So when Billy Strings walked out in Spokane on May 22, center-stage guitar in hand, and joined Bob on “All Along the Watchtower,” it felt rare and special. The song had yet another new arrangement, making it the highlight of the show for many fans.
Billy Strings had played his own set earlier on the Outlaw bill, then added clear, strong guitar playing to an arrangement that focused more on rhythm than speed. Historic by recent standards.
2. “Garden Party” blooms in Chula Vista
On May 15 in Chula Vista, the encore wasn’t one of Bob’s. It was Ricky Nelson’s “Garden Party,” a first-time-ever performance that still managed to sound completely natural in his hands. The choice nodded to a long, lightly traced history between Nelson and Bob, and to the lyric that even name-checks “Mr. Hughes … in Dylan’s shoes.” It remained a one-night-only moment on the Outlaw run, which is part of why it hit so hard.
To me personally, watching that performance was so energizing it sparked an impulsive dash to California to catch the next pair of shows. Sometimes the music just takes the wheel. (You can read the whole story here.)
1. “Mr. Tambourine Man” returns after fifteen years
The first night in Phoenix on May 13 gave us a moment we will never forget. Bob played “Mr. Tambourine Man” for the first time since 2010. His piano was steady, his singing was clear, and it really felt like he was sharing the song with the whole room. He did not keep it in the set after that, which made the moment even more special. For a tour full of surprises and rare songs, this was the strongest sign that Bob still loves to surprise us. It was without doubt the No. 1 moment for us of the Outlaw Tour 2025.
What a ride this summer has been. The Outlaw Tour 2025 gave us shocks, rare songs, and moments that will live in memory for years to come. But as exciting as it all was, now it is time to look forward. From here on, our eyes are set firmly on the European leg of the tour, where new chapters will be written and new surprises will no doubt appear.
What were your highlights of the 2025 Outlaw Tour? Let us know in the comments!
And don’t forget: tomorrow we continue our Casper Collection Series with Part 2, bringing you more rare and never-before-seen footage from across Bob’s career. Stay tuned.
Thanks for your support,
Daniel
I saw him Sept 6 in Hartford -amazing! Desolation Row --great tempo, inflection. Romona -wonderful piano. Highway 61-- just great and closed with incredible arrangement of Don't Think Twice.
My favorite part watching from afar was the training of the audience by Bob during the last performances by making himself invisible through his clothing and the stage lighting. His own fans had already been made to appreciate the no phone use policy over the past two years and grew appreciative of it, but outdoor concert fans were used to walking, talking, taking selfies in front of the stage during the performances, etc. I didn’t see videos or reviews of all the shows, but I believe Hartford may have had the most badly behaved audience, once they realized that Dylan was doing it on purpose with people yelling at Bob and some walking out. I believe he was giving a nonverbal cue to people to listen, not look through a cell phone lens, and the music, if they heard it, or danced to it, which Bob had no problem with, was super all the way to the last show.