Sometimes the best way to move forward is to look to the past. As we look to the start of a new year, we found three 90s country songs that are the perfect soundtrack to help kick off 2026.
Videos by American Songwriter
“Heads Carolina, Tails California” by Jo Dee Messina
“Heads Carolina, Tails California” is the debut single from Jo Dee Messina. Out in 1996 from her eponymous freshman album, the song was written by Tim Nichols and Mark D. Sanders.
An uptempo, feel-good song about the excitement of a future together, wherever they are, “Heads Carolina, Tails California” says, “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.”
In 2022, Cole Swindell released “She Had Me At Heads Carolina“, paying tribute to Messina’s early hit.
“I Like It, I Love It” by Tim McGraw
Sometimes life just needs to be grabbed by its proverbial horns. It’s exactly what McGraw sings about in “I Like It, I Love It”. Out in 1995 on his All I Ever Want record, Jeb Stuart Anderson, Steve Dukes, and Mark Hall are the writers of the song.
“I Like It, I Love It” is about a guy falling hard for a girl. The song says, “But I like it, I love it, I want some more of it / I try so hard, I can’t rise above it / Don’t know what it is ’bout that little girl’s lovin’ / But I like it, I love it, I want some more of it.”
McGraw still performs “I Like It, I Love It” today. The song’s success is a bit surprising, at least to McGraw, who admits he wasn’t a big fan of the song, at least at first.
“I didn’t think much about recording it,” McGraw admits (via The Boot). “I was kind of cold on it, and I listened to it again, and for some reason, it hit me a whole lot different the second time around. And then when we went in and cut the track, the track just turned out so fun and so cool that it really didn’t matter how much I liked it anymore after we got to the track, because I loved it after that.”
“How Do You Like Me Now?!” by Toby Keith
Few songs feel as good as Toby Keith’s “How Do You Like Me Now?!”
Written by Keith and Chuck Cannon, the song came out in 1999. It serves as the title track of Keith’s fifth studio album.
“How Do You Like Me Now?!” is a song about being sure of yourself, perhaps even cocky. It tells the story of a man who was never good enough for a girl he liked. Later, he becomes successful, as Keith did. The song says, “How do you like me now? / Now that I’m on my way / Do you still think I’m crazy standing here today? / I couldn’t make you love me but I always dreamed about livin’ in your radio / How do you like me now?“
“A lot of people become successful after they’ve been told they won’t ever be,” Keith says (per Songfacts). “So people can relate to this. It can be about an old flame or a boss or a teacher – whatever it means to each individual. It was a fun song to write.”
Photo by Paul Natkin/Getty Images
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