Frank Micelotta Archive/Getty Images

Marrying your high school sweetheart may sound like something straight out of a Hallmark movie, but the truth about Alan Jackson's marriage is that is was not always smooth sailing. Times were tough for the newlyweds, with Alan working at various odd jobs during the week, and playing gigs on the weekends, while Denise Jackson worked as a flight attendant. At one point, Alan sold his car to buy the couple's first home. However, fame and fortune changed everything for the couple, and taught them "A Lot About Livin' (and a Little ʼbout Love)." Rumors of the singer's infidelity began to surface, and the couple, who had been together since their teenage years, found it hard to stay afloat. "In my mind, I had all these visions that I was gonna be the star wife, I was gonna be on the tour bus with him, I was gonna be living the dream with him," Denise told "The 700 Club" during an interview. "And in reality, it was not like that at all."

The couple split up in 1997, and Denise found herself depressed and alone with their three young daughters. "I think Alan got to a point after 18 years, where he thought, 'Ya know we both deserve so much more than this, and we haven't been able to fix it yet, and I don't think it's fixable,'" she shared. "He said 'Enough is enough, and I'm leaving.'" The couple stayed apart for four months before deciding to give their marriage another shot.

Rick Diamond/Getty Images

After working through his infidelity and their separation, you'd think Alan and Denise Jackson, would be headed for smoother waters. But just because you are one of the most famous country artists in the world doesn't mean that your troubles are behind you. The strength of the Alan's relationship was once again tested when Denise learned she had colorectal cancer. In an interview with Coping Magazine, Denise recalled the poor timing of the news. "We were in Florida celebrating our anniversary when I got the call from my doctor," she recalled. 

Denise, who said had always been the picture of good health, was stunned, as was her superstar spouse. They cut their trip short and returned to Nashville to plan out the next steps, which included radiation and chemotherapy. "It was the first time I felt like I was living out the phrase in our wedding vows 'For better or for worse,'" Alan said. Drawing on what he does best, the country superstar picked up his guitar and expressed his feelings about the tragic news through the song, "When I Saw You Leaving." "A few weeks after Denise's diagnosis, this song just sort of came to me," he said. "The lyrics reflect the thoughts and feelings I had during that time." Denise is now cancer-free, but said the experience changed her life, making her realize what's important. "Cancer has had a tremendous impact on me, but it's not going to define me."

His wife's cancer diagnosis wasn't the only time that Alan Jackson let music tell his story. When his mother, Ruth, died, she left a gaping hole in her only son's life that he attempted to fill with song. He penned the tune, "Where Her Heart Has Always Been," for his mother's funeral, and the recording features Ruth reading a passage from the Bible that his sister had recorded months before as a way for Jackson and his siblings to remember her voice. "I was just so happy to get that. And I just think it makes the song," he told Yahoo Entertainment.

"Mama Ruth" was a driving force in Jackson's life. She juggled her roles of wife, and mother of five, with her career as a dietitian and school cafeteria manager. Jackson loved his mother's cooking so much that he always had one of her pies included in his backstage catering for a taste of home. He told The Boot that it was a "lemon icebox kinda pie." "It was one of my favorites but not everybody likes it, you know," he said, as he recalled that legendary Merle Haggard was not a fan. It was at his mother's urging that the country artist dabbled in gospel sound with "Precious Memories," an album filled with songs from the Baptist hymns of his youth, with very little enhancement. "I wanted to make them feel like they did when we sang them in church," he said per WTSP News. He presented his mom with the album as a Christmas gift before she died.

Fresh from the grief of losing his mother, Alan Jackson was dealt another tragic blow. His oldest daughter, Mattie, lost her husband Ben Selecman in a tragic boating accident, less than a year after their wedding. It was a tough blow for the entire family, but Jackson, who is surrounded by women, took it especially hard. "When he died, I was kind of pissed off at the world. I just wasn't feeling right about anything," he shared in an interview with Hits. "You know how I was raised: I grew up with four older sisters, then Denise and our three girls. It's all I was ever around: girls and women. So having a son-in-law was having a boy I could fish with, work on cars and stuff with. It was tough losing him so suddenly — so jarring to all of us. I lost something I'd never had before."

As it turned out, the man who wrote "A Man Who Never Cries," became quite emotional with the blows life was dealing him. "Honestly, I am pretty emotional," he continued. "I'm just a person who has a lot of sentiment. I grew up with all that. If I hadn't had country music ... it's like going to church: the feeling and the healing." For his fans, Jackson's song lyrics offer a way to cope with their feelings and healings, too, which is what he intended. As he told Yahoo Entertainment, "A lot of them are real personal, but I've always tried to write them where they're just not about me."

Jason Kempin/Getty Images

With hit after hit after hit under his western belt buckle, it seemed that nothing could stop the Alan Jackson train. And then the music suddenly stopped. The one-two punch of losing his mom and his son-in-law proved to be too much for the country crooner and he stopped "Chasin' That Neon Rainbow" after his hit album "Angels and Alcohol." While he continued to perform live, it would be six long years before he released his follow-up album. "I think we were pretty much on track to do an album like we typically have every couple of years or two or three years and just had some little rough spots in my life and personal things that slowed us down and set me back that we had to get through, my family and myself," Jackson told UMG Nashville, per Everything Nash. "And for several years there, I really didn't feel like writing at all and recording, and it took a while to get back in gear."

When he was finally ready to get back in the studio, a pandemic shut down the world and derailed his plans. Tired of waiting around, Jackson forged ahead. "So, we just decided to go ahead and get everybody in the studio whether they had to wear a mask or a helmet or whatever they had to wear and get in there and cut this thing," he said. The result was "Where Have You Gone," an album loaded with heartfelt tracks.

Jason Kempin/Getty Images

Just when it seemed the "Good Time" singer was back on top, Alan Jackson shared a sad health update with fans when he revealed that he was diagnosed with CMT. No, it's not another country music award. It's Charcot-Marie-Tooth disease. "I have this neuropathy and neurological disease," Jackson said in an exclusive 2021 interview with Today's Jenna Bush Hager. He added that the genetic disease, which he said he inherited from his father, isn't fatal, but it is incurable. "It's not going to kill me. It's not deadly," the singer said. "But it's related (to) muscular dystrophy and Parkinson's disease."

While the news may have come as a shock to his fans, Jackson has known about it for years. He revealed that he was first diagnosed more than 10 years before he announced it, but decided to go public as it was beginning to affect his balance on stage. "And it's getting more and more obvious," he continued. "And I know I'm stumbling around on stage. And now I'm having a little trouble balancing, even in front of the microphone, and so I just feel very uncomfortable." 

Contrary to what the name might lead you to think, Charcot-Marie-Tooth disease doesn't affect your mouth. According to the Mayo Clinic, it causes damage in the peripheral nerves, primarily affecting the arms and legs. At the time of his announcement, Jackson said he planned to continue performing for as long as he was able. 

Jason Kempin/Getty Images

Despite his best efforts to continue delighting fans in concert, the truth about Alan Jackson's neurological disorder was that it was progressing. The beloved performer was forced to announce his retirement from touring less than two weeks after receiving a standing ovation after a performance at the ACM (American Country Music) awards. During the Milwaukee stop of his "Last Call: One More for the Road" tour, a visibly emotional Jackson made the difficult announcement that the performance would be his last. "Y'all gonna make me tear up out here," he told the audience who gave him a long round of applause, per Parade. "But I will say, this is my last road show out here, but we're planning on doing a big finale show in Nashville next summer sometime," he shared. "It just felt like I had to end it all where it all started. And that's in Nashville, Tennessee. Music City."

Jackson's illustrious career has made him a very wealthy man, and he's put his money where his mouth is by donating a portion of ticket sales from his last tour to CMT research, raising more than $2.25 million. He expressed his gratitude to his fans at the last show. "I just have to thank y'all for supporting my music all these years, coming to the shows, buying the records and having a good time with us," Jackson said, per Music Row. The date of his final Nashville concert is TBD, but is tentatively scheduled for summer 2026.