Now, 25 years later – when many of his peers have slowed it down and dialed it back – the superstar has announced a big new tour to celebrate his silver anniversary.
Jackson's 25th Anniversary Keepin' It Country Tour will kick off Jan. 8, 2015, in Fort Myers, Florida, and wrap up May 17 at Denver's Red Rocks Amphitheatre.
"I've been touring so long, I didn't want people to be thinking, 'Gosh, here comes Alan Jackson again,' " the singer modestly told PEOPLE.
"I have fans who have been coming to my shows for 25 years, I meet them and they'll pull out a picture they took of me 25 years ago! This is a way to make it new – put together something special that pulls together those 25 years. Some people don't like to talk about how many years they've been around – it makes them feel old. I'm proud of it and glad to do it."
He's also proud to introduce two new artists who snagged the coveted opening slots on the tour: Jon Pardi and Brandy Clark. "Of all the new guys I've heard, I like that Jon is closer to country than most of the others and I thought his songwriting was better than what I've heard in a while," Jackson said.
"And I love Brandy's songwriting," he added. "There's a song on her album [12 Stories] "In Some Corner" that I thought about covering on the new album. I really studied it. It's written from a girl's perspective, and I couldn't figure out a clean way to make it come from a guy. She's really a talented singer. She sounds new and old at the same time."
The tour isn't the only commemoration of the career milestone: In August he, his wife Denise and their daughters Mattie, Ali and Dani cut the ribbon on a new exhibit in the Country Music Hall of Fame – Alan Jackson: 25 Years of Keepin' It Country – that will be on display through March 15, 2015.
New Album Also DueIn early 2015, Jackson plans to release an album of new songs that will no doubt be reflective of a quarter century that he admits has flown by.
"Once your career takes off, if you're lucky like I was, it just feels like it goes from nothing to everything overnight," he said. "It goes so fast, it's hard to absorb it all, to even appreciate it as much as you should while it's happening. Golly, I've played for four presidents and been to just about everywhere in the world, I've played in crummy little bars and big arenas and everything in between. I've been lucky to have a career that has lasted that long."
In December, he has another long-term anniversary to look forward to: "The only thing not 25 years this year is Denise and me – we're 35 years married this December," he shared. "Our youngest is a senior, she graduates in May, and next August she'll be off to college. The time has flown by, but it will be good. If they do well and they're happy out there, that's the main thing. It's kind of a new stage of our lives, and Denise and I are looking forward to it. We'll always be home to our girls, wherever we are."
Tickets and information for the 25th Anniversary Keepin' It Country Tour can be found at alanjackson.com.
January 8, 2015 Fort Myers, FL Germain Arena
January 9, 2015 Tampa, FL USF Sun Dome
February 20, 2015 San Diego, CA Valley View Casino Center
February 21, 2015 Laughlin, NV Laughlin Events Center
February 27, 2015 Los Angeles, CA Nokia Theatre (LA Live)
February 28, 2015 Phoenix, AZ AK-Chin Pavilion
March 6, 2015 Dallas, TX Verizon Theater at Grand Prairie
March 27, 2015 Augusta, GA James Brown Arena
March 28, 2015 Greenville, SC Bon Secours Wellness Arena
April 9, 2015 Wilmington, NC North Carolina Azalea Festival
April 17, 2015 Kansas City, MO Independence Events Center
April 18, 2015 Enid, OK Enid Events Center
April 24, 2015 Roanoke, VA Civic Center Auditorium
May 1, 2015 Sioux City, IA Tyson Events Center
May 2, 2015 Brookings, SD Swiftel Center
May 8, 2015 Green Bay, WI Resch Center
May 9, 2015 Bloomington, IL US Cellular Coliseum
May 16, 2015 Salt Lake City, UT USANA Amphitheater
May 17, 2015 Denver, CO Red Rocks Amphitheater