Jo Dee Messina’s ‘Heads Carolina, Tails California’: Story Behind the Song

by Katie Maloney

What inspired Jo Dee Messina’s debut single turned number one hit song?

The song was Messina’s debut single from her self-titled debut studio album. “Heads Carolina, Tails California” spent 23 weeks on the Hot 100 songs chart peaking in the number one spot. The song is about a woman proposing that she and her partner escape to a new city. During the song, Messina sings, “Heads Carolina, tails California. Somewhere greener, somewhere warmer. Up in the mountains, down by the ocean. Where it don’t matter, long as we’re goin’ somewhere together. I’ve got a quarter. Heads Carolina, tails California.”

But what’s the story behind the song? Songwriters Mark D. Sanders and Tim Nichols share what inspired them to pen the song.

Jo Dee Messina’s “Heads Carolina, Tails California”

Which Book Inspired The Number One Hit Song?

Nichols reveals that he started writing the song after listening to a book on tape. Nichols said that he listened to the renowned book, The Bridges of Madison County and was so inspired by the author that he wanted to listen to another of his books. During an interview, Nichols reveals which book on tape inspired the song, “Heads Carolina, Tails California.”

‘So, I listened to that and I was like, ‘Okay, cool.’ Then I was like, ‘Well, what else has [Robert James Waller] got?’ And I picked up this book called Border Music,” said Nichols.

Nichols said that he had about a 20-minute drive from work and back every day. During this time, he listened to Border Music on tape.

“The main character’s name was Texas Jack Carmine. Things were not going well for him in Texas so he decided he needed to leave Texas and the way he was going to decide where to go was going to flip a coin. Heads he was going to go to California and tails he was going to go to Mexico,” said Nichols.

Songwriters Put A Demo Of The Song In Jo Dee Messina’s Mailbox

Sanders adds that he was excited when Nichols came to him with the idea for the song.

“Tim told me that idea and you know, my mind just starts working. I’m from California and I always thought Carolina is a beautiful word to start with. It has a mystique to it. There is a coast on Carolina. There is a coast on California. But I knew that California and Mexico didn’t work,” said Sanders.

Nichols says that the two wrote the song in just one day. Once the song was complete, Nichols said that he “just knew” the song was meant for Jo Dee Messina. He believed in the song so much that he put a demo in Messina’s mailbox.

“I had heard in the wind that they might be looking for a song that [Jo Dee] could do as a duet. So, I called Mark and said, ‘Man, I think ‘Heads Carolina, Tails California’ could be the perfect song for them.’ I called her [because] I just felt it. I said, ‘Jo Dee, this is the song. I’ve got the song.’ She said, ‘Well just put it in my mailbox,'” said Nichols.

That’s exactly what he did and the rest is country music history.