Jo Dee Messina: Finding Her Strength

When thinking about ’90s country, Jo Dee Messina’s name is sure to be at the top of the list when it comes to hitmakers. With nine No. 1 hits and 16 Top 40 songs released throughout her career, Messina had a hand in creating the soundtrack for a decade. From “Heads Carolina, Tails California” and “I’m Alright” to “Bring On the Rain” and “Burn,” the Massachusetts native made an indelible mark in music.

Now, Messina’s getting nostalgic with the release of her first-ever limited edition vinyl record of hits, titled Heads Carolina, Tails California: The Best of Jo Dee Messina. The album features 11 of Messina’s classic hits, including “Bye Bye,” “Lesson in Leavin’,” and “Stand Beside Me” to name a few.

“It’s amazing to look back over a catalog and have so many songs with so many memories attached,” says Messina. “Now, to have them come out on vinyl? Wow! It’s a new way to hold those memories. It’s very exciting.”

American Songwriter caught up with Messina to talk all about those memories, her empowering hits, and her turn with faith-based music.

American Songwriter: How does a girl from Massachusetts get into country music? 

Jo Dee Messina: I went to a school where there were kids from all over the country, and this boy from Florida was listening to country music and I loved it because it told my story. I think I was like 13. So I was right at that age where you’re like, “Nobody understands me.” And then all of a sudden, “Baby I Lied” [by Deborah Allen] comes on and I’m like, “She does; she gets me.” I loved how it just told stories of life and I related to a lot of it.

AS: What made you move to Nashville? 

JM: When my friends graduated from high school and everybody went to college, I had already been playing the clubs. My big joke was I slept through high school because I would be out Tuesday evenings playing the Blue Star in Saugus, Massachusetts, getting home at 1:30 a.m. and getting up and going to school, and just nodding out in class. That’s when I was performing, and then after that, I continued filling out my calendar and was like, “OK, I’m either gonna go to college or I’m gonna go to Nashville to try to get a record deal.” And it was quite naive. I was like, “Oh, I want a record deal, so I’m going to Nashville.” I had no clue that hundreds of thousands of other people were doing the same thing.

AS: Did you have a plan for your career? 

JM: I love that you’d give me that much credit. Did I have a plan? No, I did not have a plan. I knew this couple that used to come to see me perform in the clubs up in Massachusetts, and so I stayed with them for a little bit, and then the first few years I was in Nashville, it really was just trying to form a life, get a routine, keep a roof over my head. I did the winter without any heat, so I’d open the oven and sit in a heated blanket, either on the couch to watch TV or in the bedroom to go to sleep. I mean, that’s what kept me warm was an electric blanket. And so, I didn’t have a plan. I just knew that I had to be here [Nashville]. I was really quiet, so I didn’t go out. I didn’t drink, so I didn’t hang out at the bars or things like that. It was really by chance the things that happened that got me to where I am. I’d like to say the Lord had his hand in it because I didn’t know lots of people.

AS: Throughout your career, you’ve had nine No. 1 hits and 16 Top 40 songs. Can you believe the success that you’ve had over the years? How does it feel now?

JM: I don’t think you realize it over the years. “Heads Carolina” was my first single, and they were like, “What was that like when that topped the charts?” And I was like, “I don’t remember.” Because we were already focused on the next one. And then you’re focused on the next one and making the next record and everything comes at you really fast. So in the moment, you don’t realize, “Oh wow, this is cool. I’m doing great,” or whatever. But as I look back on it, I’m like, “I had how many in the Top 40? Did I have that many singles? I don’t know.” So you put your head down, and just move forward and at very fast speeds.

AS: Did you have the intention of making such empowering music throughout your career?

JM: I think that the content of the music about being that strong female, about pressing forward, I don’t know if that’s who I was at the moment or what I admired and wished or aspired to be. I wish I was strong enough to say “Bye-Bye” and not sit in a bad relationship, or “I’m Alright”—I loved that and just how conversational it was—or “Stand Beside Me”. It’s like, (sings) I want a man to stand beside me. I don’t know that I was that strong, but that’s what I aspired to be.

It might have inspired people through the strength of the lyrics and that kind of stuff. I did have people come up to me and say, “Man, I wish I was like you.” And I’m like, “Ooh, I’m much more of a mush than these songs,” but I’m like, “Nah, I’m still in that relationship. It’s not good. It hasn’t been good for years” (laughs). I gotta start listening to my own music.

AS: How do you think music has changed from back then to now? 

JM: I think a huge difference between the music now and the ’90s—the ’90s were more of a story in the sense of a story of life, like “The Dance” [by Garth Brooks], or “Walkaway Joe” or “She’s in Love With the Boy” [by Trisha Yearwood], or any George Strait song (laughs). They were huge story songs in the ’90s, and then now I think it’s more like a theme, like, “Hey, let’s have fun and let’s party.” It’s starting to open back up again of getting more of a broad spectrum of topics. Which if you pay attention to music, it does that. It narrows down. There was a point where you had Faith [Hill] and Shania [Twain] and Martina [McBride] and me and Sara [Evans] and you know, all these people. And then all of a sudden, zoom, it went back to really traditional country, and now it’s opening up again. 

AS: “Heads Carolina, Tails California” was your first single. Why did you want that to be the first introduction to Jo Dee Messina?

JM: “Heads Carolina, Tails California”—it’s funny you said what made me want it to be the introduction to me. Well, the choice was never mine. The album was done. That song was nowhere in the picture. The album was completed. We were getting ready to master it, and then one of the writers, Tim Nichols, said, “I have a song we just wrote; can I drop it in your mailbox?” And I was like, “Dude, we’re done. Like, we’re so done. We’ve been working on this first record forever. We’re done. But you can drop it in the mailbox. I will listen to it.” And I heard it. I loved the chorus. It was so free. It was so freeing. Like, flip a coin, heads Carolina, tails California, as long as we’re going somewhere together, I got a quarter. I loved that sentiment.

The first two lines of the song were different. And I didn’t get ’em. And so I was like, “The first two lines I’m not crazy about. But man, the rest of the song, I love it.” The first two lines, you ready for this: (sings) We should have known it the day they shut that paper mill down, there’d be no future for us no more in our little town. I’ve got people in Austin. And I was like, “Oh, what do you do about that?” And my producer Byron [Gallimore] was like, “You just ask the writers if they can change it.”

And I was like, “You can’t do that. You can’t ask a writer to change a song.” He’s like, “People do it all the time.” So then they changed it to, Baby what do you say? We just get lost. Leave this one-horse town like two rebels without a cause, and because I’m from Boston, I’ve got people in Boston, ain’t your daddy still in Des Moines. And then the rest of it’s the same.

It was an afterthought as far as the record was done. We had to have it pressed and mastered by a certain date to have a release by a certain date. And the only time that was available that would make those deadlines was the Fourth of July when musicians were available, studios were available, where we could actually pull this off. So we recorded that on the Fourth of July [in] 1995.

AS: How did your collaboration with Cole Swindell on “She Had Me At Heads Carolina” come about? 

JM: What had happened was, the way I found out about “She Had Me at Heads Carolina” was Tim Nichols again; he’s always been like a great confidante here. He sent me a message and he said, “Hey, I just wanted to give you a heads up. This song is recorded and it’s gonna be a part of Cole’s new record.” And so I was like, “Oh, that’s, that’s cool.” It was right before the album was released. Someone reached out to somebody, I can’t remember who it was, and just touched base about, “We’re gonna shoot a video for the song. Would you like to be a part of the video?” And they were like, “Hey, what if we did a remix of the song?” And so it kind of snowballed from there. It was fun. It was a lot of fun. And what I said to the songwriters was, “How amazing a song is it that you wrote something that brings joy to generation after generation?” I’m like, that’s quite an accomplishment for the writers.

AS: You didn’t write any of your greatest hits that appear on the vinyl record. Were you not writing at that point?

JM: I did not write them. I think I was so just insecure. I was trying to please—I was just like, “Here you go, the best song wins. It doesn’t have to be my song. It has to be the best song.” And so I would bow out a lot of times in submitting stuff that I had, or a few things that I wrote made the record, but I would listen down and I’d be like, “Nah, I like ‘Bye-Bye’ better.” And I think that was due to my own insecurity of my writing at that point. These days, [it’s] totally different (laughs). I’m writing up a storm, and for other people as well, which is a blast. 

AS: What does your songwriting process look like? 

JM: Somebody could say something and I’m like, “Oh yeah, that’s a song title,” or  I’m thinking of something, I don’t even know why, I’m like, (sings) my heart belongs to Jesus. Nobody else will do my heart. I just have a thought or an emotion that comes out in a song. It’s an idea or a thought or something that strikes me in life.

AS: When did you start writing more faith-based songs? 

JM: It was about 2014, I’m guessing, ballparking, that I really started to recognize the realness of Christ who stepped into my heart, who shifted my center. And I was like, “Why doesn’t everyone know this?” I am a Christian because I’m not Jewish and I’m not this or that, I’m not other things, so I must be a Christian, right? But I didn’t really understand what that meant. And when you can have a relationship with Christ, who is the God who made us, no one knows you better. No one knows you better, even your best friends, you’re always hiding something or this or that storyline of your life. He knows it all and still loves you. And that’s just huge to me. You know, people are like, “I found Jesus.” I’m like, “Well, he found me and I knew it like I knew, like I knew.” And so I wanna share that with someone, especially people that are hurting.

AS: Would you say you found your voice through faith? 

JM: I think I found the strength to speak because it’s like, “Well, OK, if this is true to him, then it’s OK.” The Bible tells us it’s not always easy to walk with Christ, but you’re also never alone with him. He’s always there. 

AS: You announced your Heads Carolina, Tails California Tour earlier this year. What can we expect?

JM: Yes, we are finally doing, finally, after 375 years, we’re gonna do the Heads Carolina, Tails California Tour. Never have we toured under that umbrella. We’re going out, we’re kicking it off in … Carolina, and we’re gonna end it in … California (laughs). And we’re gonna hit just about every place in between throughout the year. But I’m excited. We’re going way back, like retro. Everything’s retro. We found posters from my first album, and they’re still together, so they did a great job making them. But we’re gonna have those as limited merch throughout the tour. It’s gonna be really exciting. We’ll have all the hits, then we’ll have unique merchandise and new songs, so that’s where I’ll start to debut some of the new songs as they come about. It’s just going to be such a fun year.

AS: Can we expect a new album this year?

JM: It has been a while since we’ve had new music, and that’s my hope for this year is to get all these writing sessions and just put together a project that’s really me and be able to release that at some point this year.

Photo by John Zocco / 117 Entertainment