What country singer Jo Dee Messina misses most about ’90s Nashville

Any country music fan worth their salt has known all the words to Jo Dee Messina’s “Heads Carolina, Tails California” since it debuted in 1996 - and also wondering where exactly she’s been for the last decade or so.

Messina hasn’t exactly been hiding - she’s toured constantly and made occasional appearances at events like the CMA Awards - but it’s been 12 years since she released her last album, 2014’s Me. Now, she’s back with Bridges, a collection of songs inspired by everything she’s been through lately. And that, as it turns out, is a lot.

“I became a single parent. I lost my mother, and then recently, I lost my father, and then I dealt with cancer,” Messina explained in an exclusive interview with Us Weekly. “And so there’s been a lot of shake-up in the normal day-to-day, right? And oh, did I mention I have two kids? So, raising men and looking at the world through their eyes and trying to guide them - that’s a full-time gig.”

“I still feel like I’m one of them,” she explained. “We see each other and do stuff together, functions and whatever. And I’m hanging with them - I don’t remove myself in that aspect. And I just love to be a part of the get-together.”

She does, however, feel a little nostalgia for the era when she was first starting out. Because even as country music reaches ever more impressive heights, the industry itself - at least in Nashville - can feel a little hollowed out.

“I miss living in Nashville, going to Music Row, and there being houses of songwriters, one after the other one after the other one,” she told Us. “Now we’ve got these big buildings, but it used to be, ‘Hey, walk down the street. That’s where so-and-so writes, that’s where so-and-so writes, oh, that’s where so-and-so records.’”

It’s easier than ever to put your music out into the world, but Messina thinks “the accessibility of a relationship with people in the industry” was a little bit better back then. “Like, to get someone to pick up a phone these days is like wrestling an alligator,” she joked. “There used to be phone calls all the time. I used to call my manager three or four times a day!”

Despite those changes, Messina is happy to be back and sharing her wisdom, even if it meant taking an unintentionally long break from recording.

“Jo Dee on ‘Heads Carolina’ was all about starting the adventure. This one’s more like, ‘I’ve been down the road less traveled,’” she explained. “Every turn means I’ve been down multiple roads, whether it’s straight, whether it’s a turn, whether it’s whatever. And hey, look what I learned along the way.”

Bridges is out Friday, June 5.

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This story was originally published June 1, 2026 at 10:00 AM.