In the 27 years that have passed since Jo Dee Messina's bold and infectious debut single "Heads Carolina, Tails California" first made its mark on the genre, the country star has traveled through many chapters of life.

Although she's never fully stepped away from country music, Messina's everyday life looks much different than during the early years of her career. When Cole Swindell released his playful track "She Had Me at Heads Carolina" last summer, the song became a massive hit, spurring a wave of nostalgia and excitement around Messina's first single.

Swindell's song was one of the latest in a stream of recent tracks paying homage to that important era of country music, dominated by new voices and established artists bringing polished pop elements to traditional sounds. But his lighthearted tribute to "Heads Carolina, Tails California" kicked off a new chapter for Messina, reminding established fans of their favorite tune while attracting new generations of listeners to the "90s country" universe. 

Just a few months later, Swindell released a remix of his track featuring Messina and invited her to join him for a surprise duet performance during the 2022 CMA Awards two days later. During a recent phone call with Messina, she reflected on that special moment, and the kindness both Swindell and fans have shown her.

"I was just so excited to be at the CMAs and just so honored that Warner Brothers and Cole asked me to sing that song," Messina tells The Boot. "I mean, he easily could've done it himself, but he chose to have me be a part of it and was so sweet. Everything is looked at through a lens of gratitude."

That renewed interest in "Heads Carolina, Tails California" has since set off an exciting chain of events for Messina. On March 10, she released Heads Carolina, Tails California: The Best of Jo Dee Messina, her first record to be pressed on vinyl. The release features an assortment of her biggest career hits to date, from the 90s to the 2000s.

"[This project] is just me and my former label taking time to look back and celebrate the years and the times that we had together," Messina says. "Each song is like a picture in time. It's kind of cool to look back because I think when I was going through it, I didn't realize it because it was moving so fast, you know? So it's really just a way to sit back, enjoy and look at the years and the memories that we shared together."

Now, she's ready to celebrate the impact of those remarkable early hits directly with her fans. After wrapping up a successful stretch of dates supporting Reba McEntire, Messina kicked off her 2023 'Heads Carolina, Tails California' Tour, which stretches through November. 

Although the 52-year-old hitmaker has continued to consistently perform for fans over the years, this headlining trek is one of her most expansive and unique tours to date. Along with later fan favorites like "I'm Alright" and "My Give a Damn's Busted," concertgoers have a chance to hear deep cuts like her second career single, "You're Not in Kansas Anymore."

For Messina, the opportunity to celebrate the songs that started it all is a gift she isn't taking for granted. 

"It's a joy because I've been nose down, living life day to day, raising my kids, homeschooling, taking them to hockey, touring and doing live shows... you know, I just keep trucking forward," she says. "So to look back at that, it's from a position of gratitude and just... wow. What a great run."

With dozens of tour dates still ahead, Messina is focused on taking care of herself while striving toward new goals. 

"I try to stay active and focus on trying to rest and hydrate. Emotionally and mentally, I'm in the process of creating," she explains. "I've written so many songs. During these shows, I do a little songwriter segment, and I'm like, 'Oh, I wrote this song I want to share!' I get so excited about the stuff that we've been writing lately."

That passion is apparent in her songwriting, which has sparked interest from other artists, too.

"I get so excited about the stuff we've been writing lately. I got a big cut! But I can't talk about it yet," Messina teases excitedly. "It's a whole new world for me. I've always been known as an artist and not a writer. And now, my writing is just blowing up, and so there's just a lot going on. It's a good pace, so I'm just taking it one step at a time."

Until she's ready to share that big news, along with her own new batch of songs, Messina will be soaking up every moment she spends on stage, sharing her music with fans both new and old.

"Every time we go out on stage, I'm having a blast because it's a gift," she reflects thoughtfully. "It's a gift."

Jo Dee Messina Through the Years

From her career takeoff in 1999 to her surprise comeback, sparked by Cole Swindell's hit tribute "She Had Me at Heads Carolina," take a look back at these pivotal moments from Jo Dee Messina's country music career.

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