"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. The song was released in January 1996 as her debut single and served as the lead-off single for her self-titled debut album. The song reached the Top 10 on both the U.S. and Canadian country charts.

"Heads Carolina, Tails California" is an up-tempo song about a narrator who wants to just take her love and run off together somewhere, but anywhere will do as long as her love comes with her.

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.'" She goes on to say that "passion and energy permeate Messina's strong vocal attacks on this infectious tune."

A music video was released for the song directed by Roger Pistole. Messina is shown performing with an old-fashioned microphone in a run-down wooden shack in the countryside and leaning against the counter of a diner, dressed as a waitress. Throughout the video are scenes of men traveling on an old dirt road pushing tires with them. They are seen sitting in the diner that Messina is seen in, and outside of a rural gas station in which the diner is located.

"Heads Carolina, Tails California" debuted at number 70 on the U.S. Billboard Hot Country Singles & Tracks for the week of January 27, 1996.

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