Portrait of singer Jo Dee Messina at the Wisconsin State Fair in Milwaukee, Wisconsin, June 10, 1998. (Photo by Paul Natkin/Getty Images)
Photo by Paul Natkin/Getty Images

'Heads Carolina, Tails California': The Story Behind Jo Dee Messina's Whimsical Road Trip Anthem

What decides our future? Is it fate or random circumstance? Jo Dee Messina probably would've never guessed that a performance on a radio show would lead to a chance encounter that would help jumpstart the country music career she'd always dreamed of.

While performing at the Kentucky radio show Live at Libby's Messina impressed producer Byron Gallimore, who just happened to be working with Tim McGraw. McGraw and Messina became friends and eventual label mates. McGraw even co-produced Messina's debut album.

So it's fitting that Messina's debut single follows a couple who decide their future with the flip of a coin. Written by Tim Nichols and Mark D. Sanders, "Heads Carolina, Tails California" is one of the most infectious country tunes of the '90s and the perfect soundtrack to a road trip with your other half. The song hit No. 2 on the Billboard country charts in 1996 and helped establish Messina as one of the most promising new vocalists of the decade.

Messina followed up with the top 10 hit "You're Not in Kansas Anymore." Though her next two singles failed to chart, Messina made a strong comeback with 1998's I'm Alright, which spawned the hit title track, "Bye Bye" and "Stand Beside Me," which all hit No. 1 on the country charts.

"Heads Carolina, Tails California" Lyrics:

Baby, what do you say we just get lost?
Leave this one horse town like two rebels without a cause
I've got people in Boston, ain't your daddy still in Des Moines?
We can pack up tomorrow, tonight let's flip a coin

Heads Carolina, tails California
Somewhere greener, somewhere warmer
Up in the mountains, down by the ocean
Where it don't matter
As long as we're going somewhere together
I've got a quarter
Heads Carolina, tails California

We can load what we want in the back of a U-Haul van
Couple modern day Moses' searchin' for the promised land
We can go four hundred miles before we stop for gas
We could drive for a day and then we'll take a look at the map

Heads Carolina, tails California
Somewhere greener, somewhere warmer
Up in the mountains, down by the ocean
Where don't matter long as we're goin'
Somewhere together, I got a quarter
Heads Carolina, tails California

We're gonna get outta here if we gotta ride a greyhound bus
Boy, we're bound to outrun the bad luck that's tailin' us

Heads Carolina, tails California
Somewhere greener, somewhere warmer
Up in the mountains, down by the ocean
Where don't matter long as we're goin'
Somewhere together, I got a quarter
Heads Carolina, tails California

Editor's Note: This article was originally published in 2018.

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