Jo Dee Messina Looks Back on Timeless Hits; Embarks on Heads Carolina, Tails California Tour—“It’s Just Going to be Such a Fun Year”

When you think about ‘90s country, Jo Dee Messina’s name is sure to be at the top of the list when it comes to hitmakers. With 9 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.

Videos by American Songwriter

Now, Messina 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,” said 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 vinyl project of empowering hits, and her brand new Heads Carolina, Tails California Tour.

American Songwriter: Tell us about the vinyl project, The Best of Jo Dee Messina, and how it came together.  

JM: I got together with my former record label Curb Records. They wanted to put a compilation of songs together that really highlighted our time together. So, they decided to make it unique for those who are collectors. We would release it on vinyl.

I’ve never had anything on vinyl. So, I’m like, ‘I’m gonna have an album!’ like when I was a little kid, you know, they used to have albums. I remember my older brother used to get the new Rush album and you’d flip it over and you’d read all the album liners and everything, and so, now I have one of those myself.

AS: Do you have a record player?

JM: I don’t. But record players are hot these days. Everybody has them, you almost can’t buy them because everyone’s buying them right now. The vinyl is so huge right now.

AS: Throughout your career, you’ve had 9 No. 1 hits and 16 Top 40 songs. Can you look back and believe the success that you’ve had over the years? How does it feel now?

JM: I don’t think you realized 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: With these greatest hits out on vinyl, can look back over your career and say you have a favorite song?

JM: I cannot look back over my career and say, this one’s my favorite. I can say on certain days, if you’re having a tough day, maybe it’s “Bring on the Rain.” Or if you go out and do a show and everybody’s screaming “Stand Beside Me,” then it’s like, ‘Oh my gosh, ‘Stand Beside Me’ was so great tonight, or whatever. So it always kind of just depends on the day.

AS: Did you intend to make such empowering music?

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 wish 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. 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: “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, let’s just flip a coin. 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 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 you know, 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 4th of July when musicians were available, studios were available, where we could actually pull this off. So we recorded that on the 4th of July, 1995.

AS: What do you remember about recording “Burn”?

JM: The song itself, I mean, that was one of those where it was like, ‘It’s too pop, it’s too pop, it sounds too pop.’ It kind of got its own little hard time.

But I do remember shooting the video for ‘Burn.’ It was at Boldt Castle up in Thousand Islands, New York. It was October. On an island where all the water and electricity were shut off for the season. And so between takes, they would throw blankets all over me, and then I’d get up there and I’d be like, Do you wanna be a poet in this spaghetti string dress. And I’m like, ‘Whaa’ in between takes. I mean, if you saw that, it’s so funny, Stuart Dill is my manager and still is a dear, dear friend, and I was just at his house a month ago and he has a picture of us riding over to the island on a boat. We’re like underneath all the covers. The wind was so cold, the water was freezing, and then the song is ‘Burn’ (laughs)

AS: What’s the first thing that pops into your head when thinking about “Lesson in Leavin'”

JM: So my first record, Tim McGraw and I, we both watched the Dottie West story (at different times) and it was on the first album where he was like, ‘Man, you should cut that song “Lesson in Leavin'” that sounds like you’. But the label was like, ‘No, we don’t want a bunch of covers on the first record.’ So when the I’m Alright record came around, Tim was like, ‘Alright, we gotta do ‘Lesson in Leavin.'” And so we did. I loved the song and the guitar intro, now you’re gonna have to go back and listen to it. The guitar intro, it does that… (makes the guitar sound). They were joking around in the studio and they’re like, I think it was McGraw’s idea, where he’s like, how about that thing from the beginning of Loony Toons. They were joking about that and then I think it was Brent who went in there and came up with that whole guitar intro.

AS: You didn’t write any of the hits on your vinyl, why?

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, totally different. I’m writing up a storm, and for other people as well, which is a blast. 

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

JM: Yes, we are finally doing, finally, after 375 years, we’re gonna do the Heads Carolina Tales, 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.

The Best of Jo Dee Messina is available now, HERE. Watch our full interview with Jo Dee and check out her upcoming tour dates below.

Heads Carolina, Tails California: The Best of Jo Dee Messina tracklist:

1. “Heads Carolina, Tails California” (Tim Nichols, Mark D. Sanders)
2. “Bye-Bye” (Rory Bourke, Phil Vassar)
3. “I’m Alright” (Phil Vassar)
4. “Bring On The Rain” feat. Tim McGraw (Billy Montana, Helen Darling)
5. “My Give A Damn’s Busted” (Joe Diffie, Tom Shapiro, Tony Martin)
6. “You’re Not In Kansas Anymore” (Tim Nichols, Zack Turner)
7. “Lesson In Leavin'” (Randy Goodrum, Brent Maher)
8. “Stand Beside Me” (Stephen Allen Davis)
9. “Because You Love Me” (Kostas, John Scott Sherrill)
10. “That’s The Way” (Annie Roboff, Holly Lamar)
11. “Burn” (Tina Arena, Steve Werfel, Pam Reswick)

Heads Carolina, Tails California Tour Dates:

March 25 – Pigeon Forge, Tenn.
April 14 – Fort Worth, Texas
April 15 – Georgetown, Texas
April 28 – Wichita, Kan.
April 29 – Fort Smith, Ark.
May 13 – Kansas City, Kan. 
May 19 – Doswell, Va.
May 20 – Roanoke, Va. 
June 9 – Clinton, Iowa 
June 10 – Decatur, Ill. 
June 16 – Ashland, Neb. 
June 17 – Winsted, Minn.
June 23 – Raleigh – N.C.
June 24 – Virginia Beach, Va.
June 29 – Shipshewana, Ind.
June 30 – Central City, Iowa
July 13 – West Salem, Wis.
July 14 – Chicago, Ill. 
July 15 – Pierz, Minn.
July 21 – LaGrange, Ga.
July 22 – Cullman, Ala. 
July 28 – Kearney, Neb.
July 29 – Mendon, Ill.
Aug. 3 – Wausau, Wis.
Aug. 4 – Detroit Lakes, Minn. 
Aug. 11 – Atlantic City, N.J.
Aug. 12 – West Chester, Ohio
Aug. 19 – Calgary, Alberta
Sept. 7 – Carterville, Ill.
Sept. 9 – Savannah, Tenn.
Sept. 14 – Spencer, Iowa
Sept. 22 – Frederick, Md.
Sept. 23 – Mount Vernon, Ky.
Oct. 7 – Hiawassee, Ga.
Oct. 19 – Greenville, S.C.
Oct. 20 – Kissimmee, Fla.
Oct. 21 – Charlotte, N.C.
Nov. 3 – Lubbock, Texas
Nov. 4 – Waco, Texas 
Nov. 10 – Phoenix, Ariz. 
Nov. 11 – Indio, Calif.

Tickets are available, HERE.

Photo by John Zocco / 117 group

Leave a Reply

Dan Harrison Is “Crazy ‘Bout Country”: Exclusive Premiere