After over three decades of touring and a career that defined an era, Alan Jackson played his final road show in Milwaukee on May 17, 2025. But as one curtain falls, another moment is already being planned—one last encore in the city that built him: Nashville.
The end of the road, the start of reflection
At 66, Alan Jackson is not just a country icon—he’s a living embodiment of the genre’s heart, voice, and stories. And on May 17, inside the Fiserv Forum in Milwaukee, he officially brought his road-touring days to an emotional close. The show marked the end of his Last Call: One More for the Road tour, and with it, a chapter of American country music history.
Addressing a packed house of fans, Jackson delivered the announcement in a moment laced with both gratitude and nostalgia. “Y’all may have heard that I’m kinda winding down. In fact, this is my last roadshow of my career,” he said, pausing as the crowd erupted in cheers. “Y’all gonna make me tear up out here.” And with that, the man who once sang “Where Were You (When the World Stopped Turning)” gently signaled that the road had, at last, turned homeward.
A dream born in a U-Haul
As Jackson spoke from the stage, he looked back on the journey that began over 40 years ago. “It started 40 years ago this September,” he recalled. “My wife and I drove to Nashville with an old U-Haul trailer and chased this dream.” That dream, fueled by grit and a deep reverence for country tradition, grew into a career that saw 26 number-one hits, over 75 million records sold, and a firm place in the Country Music Hall of Fame.
“I lived the American dream, for sure,” Jackson said. “So blessed. Thank you all so much for all your support of my music and attending my shows.” For fans in Milwaukee—and across the country—his farewell wasn’t just a goodbye to touring; it was a thank-you from a storyteller who had always been one of them.
The diagnosis behind the decision
Jackson’s retirement from the road didn’t come lightly. In 2021, during an emotional appearance on the Today show, he publicly revealed he had been diagnosed with Charcot-Marie-Tooth disease, a hereditary neurological condition that affects muscle function, balance, and mobility.
“I’ve been reluctant to talk about this publicly,” he admitted at the time. “But it’s starting to affect my performance onstage a little bit where I don’t feel comfortable.” With characteristic humility, he added, “I don’t want people to think I’m drunk onstage.” While the condition isn’t fatal, Jackson noted that it is progressive and would eventually make performing more difficult.
Even in the face of that reality, Jackson kept singing. He launched the Last Call tour in June 2022, determined to give fans a proper farewell and one final opportunity to sing along live. That decision spoke volumes about the depth of his dedication—not just to his career, but to the people who had supported it for so long.
A tease of one final encore
Though Milwaukee marked his final road show, Jackson hinted during the performance that this wasn’t quite the end. “We’re planning on doing a big finale show in Nashville next summer sometime,” he told the audience. “I just felt like I had to end it all where it all started, and that’s in Nashville, Tennessee.”
The significance of Nashville in Jackson’s journey can’t be overstated. It’s the city where he pitched songs from the trunk of his car. It’s where he recorded his breakout hit “Here in the Real World.” And it’s where he rose from hopeful songwriter to one of the genre’s most decorated legends. A final show in Music City isn’t just poetic—it’s full circle.
For longtime fans, the promise of one more show offers both comfort and anticipation. Jackson may be stepping off the road, but he’s not stepping away from the music—not yet.
A moment etched in awards and memories
Just days before the Milwaukee show, Jackson took the stage at the 2025 ACM Awards, performing his beloved ballad “Remember When” to thunderous applause. The performance was made all the more poignant by the occasion: he was honored as the first-ever recipient of the Alan Jackson Lifetime Achievement Award.
Accepting the award, Jackson shared a sentiment that struck at the core of his appeal. “I came to Nashville with a paper sack full of songs and a crazy dream,” he said. “And that all these years later I’m standing here receiving such an honor is mind-blowing.”
There’s an enduring humility in his voice, a groundedness that has never wavered through decades of fame. Jackson has always sung for the everyday American—the factory worker, the farmer, the small-town dreamer. His success never distanced him from his roots; it only deepened his connection to them.
The legacy left behind
As Jackson exits the touring spotlight, what remains is a towering legacy. He’s credited with keeping traditional country music alive in an era of pop crossover. His music was never about flashy production—it was about stories, steel guitars, heartbreak, and hope. And he didn’t just preserve country music; he pushed it forward by remaining uncompromising in his sound and identity.
Through chart-toppers like “Chattahoochee,” “Drive (For Daddy Gene),” and “It’s Five O’Clock Somewhere,” Jackson offered an authentic southern perspective with a laid-back charisma that never went out of style. His songs weren’t just radio hits—they were soundtracks for millions of American lives.
In a genre that often grapples with reinvention, Alan Jackson remained steadfast. He stood as a reminder that authenticity never ages, and that sometimes, the best innovations come from staying true to the roots.
The ride may be over but the music plays on
“It’s been a long, sweet ride,” Jackson told his fans on May 17. And it has been. His journey has spanned arenas, barrooms, award shows, and family backyards. He has offered America not just songs but chapters of its own collective memory, told through the lens of love, loss, and late-summer nights.
As he readies for that final show in Nashville, Alan Jackson leaves the road with the same grace he traveled it—with a guitar in hand, a story to tell, and a heart full of thanks.
The ride may be over, but the road he paved is one that countless country artists will continue to walk. And for the fans? His voice will forever be one that makes the jukebox feel like home.
