Jo Dee Messina is an under-sung hero of 90s country. Her signature song and debut single, ‘Heads Carolina, Tails California’ is one of the most joyous songs from country radio’s golden age—all sunny guitar riffs, immaculate phrasing and warm Nashville gloss.
Now a permanent fixture on throwback country stations and streaming playlists, ‘Heads Carolina’ introduced Messina to the world and kicked off an impressive run at radio. Messina notched five no.1 hits between 1998 and 2001, with a sixth chart-topper—the deliciously petty ‘My Give a Damn’s Busted’, originally recorded by Joe Diffie—arriving in 2005.
It would be another 9 years before Messina released her next studio album—the Kickstarter-funded Me, which she released independently—as label troubles prematurely halted her career as a regular hit maker. But true to her endlessly upbeat songs, Messina kept the faith, and she’s now seeing a creative and commercial resurgence.
At last year’s CMA Awards, Messina joined Cole Swindell for a surprise duet performance of his hit, ‘She Had Me at Heads Carolina’. The song, a cheeky reinterpretation of Messina’s classic, reached No. 1 on Billboard’s Country Airplay Chart last year, owing to Swindell’s charismatic delivery and a healthy dose of 90s nostalgia.
Fittingly, Messina’s iconic song lends its title to Messina’s new greatest hits collection, Heads Carolina, Tails California: The Best of Jo Dee Messina. Trimmed to a tight 11 tracks and clocking in under 40 minutes, the album is a no-skips joyride and high-energy introduction to all the vocal powerhouse has to offer.
Messina spoke to Holler to reflect on her path to stardom and share what makes the new collection special.
Why was now the right time to put out a greatest hits album?
Well, Curb Records—my former label—reached out to me early last year and said they were looking at the streaming of my catalog and the numbers were really impressive. So, they asked me, “What if we put this project together to celebrate the years that we had together and press the songs in a way that no one's ever heard them?” I've never been pressed on vinyl, so that's all new to me. It was actually supposed to come out in November, but the pressing got it kicked back a little.
What was the process like of deciding which songs to include?
It was really hard. I believe they went off of streaming success, radio success, familiarity—those kinds of things. The label approached me with the list of songs and I was like, “Yeah, this is good.” [Laughs] I just kind of looked at it and said, “Wow. What a run we had.”
You moved to Nashville from Massachusetts at 19 to pursue a country music career. What was that like?
I started singing and performing live when I was 13 or 14, did it through high school and then everyone went off to college. I knew I either needed to go to college or go to Nashville and really give the singing thing a shot. And I didn't know anybody. My brother drove down with me and I spent the first couple years just trying to keep a roof over my head and singing whenever I could, which wasn't as often as I did back home. But I would enter talent contests and things like that. I won a talent contest and that gave me a chance to perform on a live radio show. Then I became a regular on a live radio show and that's when my producers heard me.
Was there a specific moment when you realized you had made it?
When I look back at it now, I can see, “Wow, I remember this song. I remember this moment in time.” But at that time, everything was moving so fast. It was always about getting to the next thing: the next album, the next record, the next video. Looking back at it now, I don’t know that there was ever a moment where I was like, “Alright, I made it.”
Did you ever doubt that you would become a country star, or did you always know that it would work out?
I never knew anything. I did know that I definitely wanted to do it, but I wasn’t brave and strong and mighty; I was naive. I didn't realize that everyone else came to Nashville for the same thing. Really, I was just lucky and fortunate to meet the people I did when I did and have the records I had when I had them.
‘She Had Me at Heads Carolina’ has been such a moment in country music over the last year. What did you think when you first heard what Cole Swindell did with your song?
Tim Nichols, one of the original writers of ‘Heads Carolina, Tails California’, sent me a copy of the song before it came out and said he wanted to give me a heads up. And I thought it was neat. It’s pretty cool to have somebody recognize your song as something that you hear at karaoke all the time—which you do! If you’re ever in downtown Nashville, you hear people doing that song all the time, coming in and out of watching the Predators game, or whatever it is.
Speaking of karaoke, do you have a go-to karaoke song?
I don’t karaoke. [Laughs]
Maybe a couple times, when my friends and I went camping or something. But I’m a mom of two boys right now, and I’m homeschooling them. When I go out, it’s to work and other than that I’m home with my kids. Maybe one day I’ll hit the karaoke bar.
I loved watching you perform that song at last year’s CMAs. What was that experience like?
If you go back and watch the performance, you can tell that I had a blast. There was no pressure on me. I just felt so honored that Warner Brothers and Cole asked me to be a part of that performance. I was blown away and just enjoying every second of it.
You came up during the peak of women on country radio in the 90s. What has it been like to see the number of women on radio dwindle over the years?
Well, you have to look further back. It ebbs and flows, because when we came out, it was on the heels of it being a male-dominated format. Then it flipped, and it was a female-dominated format, and then it flipped back. Now, with the Lainey Wilsons and Carly Pearces of modern country, you’re seeing it come back around. If you talk to someone like Dolly Parton, who’s been in the industry even longer, she will tell you the same thing.
The same argument can go for people who say, “That’s not country”. There was traditional country, and then came Dolly with ‘9 to 5’ and ‘Here You Come Again’. Then it went back to being more traditional and then there was Shania. All of these things ebb and flow, and you just wait for it to come back around.
You’ve worn many hats over the years, and I’d be remiss if I didn’t ask you about guest-starring on The Real Housewives of Atlanta. What was that like?
It was fun. I was just talking with [music producer] Lil Ronnie, who was on that show with me a few weeks ago. He’s now married and has kids as well. Actually, I was pregnant when we filmed that show. They asked me to be a part of it from a songwriting standpoint, and I told them I didn’t want to be in any type of drama, especially because I was pregnant. And they agreed and said they just wanted me to be a part of the show. So, when I met with Kandi [Burruss] and Ronnie to write, it was just such a joyful experience. It was a great time.
Does this record mean new music is on the horizon?
Yes! We have a single that’s coming out soon, like in the next couple of months. I’ve been doing a lot of songwriting, and this song just struck so many people. Publishers, co-writers, producers, other artists—people are like, “You need to get the song out there.” So, we are in the process of mixing and mastering the first song in a while, and I’m excited for that to come out.