Songfacts®:

• In this song, Jo Dee Messina wants to up and leave, and she doesn't care where, as long as her man goes with her. To decide their destination, she wants to flip a coin: if it's heads, they go to Carolina, tails, it's California.
  
  It's a romantic song in the spirit of Bruce Springsteen's "Born To Run," where the destination doesn't matter as long as they're together. These songs date to a time when it was very easy to disappear; unless you called from a phone booth or sent a postcard, no one would know where you were.
• "Heads Carolina, Tails California" was Jo Dee Messina's first single, and the song that put her on the map. It was released in 1996, seven years after she moved to Nashville from Massachusetts. It's a great introduction to Messina, who is all about living life to the fullest. The song made a connection, rising to #2 on the Country chart and setting her up for success. Her next album, I'm Alright, was released in 1998 and had three #1 Country hits: "Bye Bye," "I'm Alright" and "Stand Beside Me."
• The song was written by the Music City songwriters Mark Sanders and Tim Nichols. Sanders got the idea after listening to the 1995 audio book version of Border Music by Robert James Waller, better known for The Bridges of Madison County. The main character, Texas Jack Carmine, decides he needs to leave Texas, so he flips a coin to decide if his going to go to California or Mexico. Sanders knew Mexico wouldn't work in the song, so he changed that option to Carolina.
• When this song took off, Messina's label asked its writers, Mark Sanders and Tim Nichols, for another song with a similar theme. They delivered a tune called "I'd Rather Ride Around With You," with was rejected because it was too similar. That one went to Reba McEntire and went to #2 on the Country chart.
• The song was shopped around to different artists before it landed with Jo Dee Messina. The writers changed some of the lyrics to personalize it to her, particularly "I've got people in Boston," since she's from Massachusetts.
• The 2022 Cole Swindell hit "She Had Me At Heads Carolina" takes place in a karaoke bar where he falls for a girl who sings "Heads Carolina, Tails California." Swindell's song gave Jo Dee Messina's tune a big lift, introducing it to a younger generation. Messina appears in the video, playing the bartender.
• Jo Dee Messina enjoyed a revival in the 2020s thanks to "She Had Me At Heads Carolina" and a wave of young country singers who cited her as inspiration.
  
  "All thanks to the glory of God," she told American Songwriter. "It surprises me - I was always just running my own race. But it opens the door to share the Lord with the younger generation coming up, which is my heart's desire these days. It creates a path, a bridge, for me to share what's important, reflecting on my own walk and what really matters."
  
  "I have more wisdom now than I did then," she added. "You don't have to sacrifice your entire belief system just to be successful."
• Messina joined Cole Swindell to perform at both the 2022 CMA Awards and the 2023 ACM Awards, where Swindell sang "She Had Me At Heads Carolina" and Messina then joined him on stage to segue into "Heads Carolina, Tails California." Swindell seemed thrilled to have her on stage and made sure to call out her name.