Alan Jackson’s Grandsons Attend Their First Concert—And It Was Grandaddy’s Show
To the world, he’s a country music legend. But to two little boys in Tampa, Florida, he’s simply Grandaddy.
Alan Jackson gave a performance to remember during his Last Call: One More for the Road tour on April 26—but it wasn’t just the sold-out crowd at Amalie Arena who made the night special. It was the presence of his two youngest fans: his grandsons, Jackson Alvie Bradshaw, age 2, and Wesley Alan Smith, just 10 months old—attending their very first Alan Jackson concert.
The boys, sons of Jackson’s daughters Alexandra and Mattie, not only experienced the music—they made it onto the big screen, smiling and waving from their seats as cameras panned the audience. The moment, beaming across the arena, had the crowd cheering.
Mattie, Alan’s eldest daughter, captured the magic in an emotional Instagram post:
“This weekend Ali and I got to take our boys to their first Alan Jackson show. There’s no telling how many shows I’ve been at in my life, but my goodness was this one special for all of us.”
She also shared a photo carousel full of tender family snapshots: Jackson and Wesley in matching headphones, the girls with their husbands, and the entire family—Alan, wife Denise, their daughters, and grandkids—gathered together on the tour bus in a moment of quiet pride.
One standout shot shows Alexandra, Mattie, and their sons smiling up at the screen, the image immortalized for thousands to see—and for two little boys to remember when they’re old enough to understand who their grandaddy really is.
“Wesley’s too young to get it, of course,” Mattie wrote, “but to have pictures and videos and memories of their Grandaddy perform is priceless to say the least. Very thankful for this little bitty moment.”
Set to the soundtrack of Alan’s classic “Little Bitty,” the post resonated with fans, many of whom have followed Jackson’s career—and his family—through the years.
Alan and Denise Jackson have three daughters: Mattie, Alexandra, and Dani Grace. Now, as a grandfather, the singer seems to be savoring this new chapter with the same grace that’s defined his career.
With just a few stops left on his farewell tour—including a performance at the 2025 ACM Awards on May 8 and a final show in Milwaukee on May 17—these are precious final moments in a life that’s been lived largely on the road.
And now, with his grandsons watching from the crowd, Alan Jackson’s legacy feels more personal than ever.