"Heads Carolina, Tails California" is a song written by Tim Nichols and Mark D. Sanders and recorded by American country music artist Jo Dee Messina.

American Aquarium covered the song on their 2021 album Slappers, Bangers, and Certified Twangers: Vol 1.

Deborah Evans Price, of Billboard magazine reviewed the song favorably, calling it a "rollicking country ode to flipping a coin and hitting the road in search of a better life 'somewhere greener, somewhere warmer.'

[3] A music video was released for the song directed by Roger Pistole and filmed in the Mojave Desert.

Messina is shown performing with an old-fashioned microphone (a Shure Unidyne Model 55) in a run-down wooden shack in the desert and leaning against the counter of a diner, dressed as a waitress.