Eighteen ’90s Country Songs That You Loved But May Have Forgotten About

Doug Stone
Doug Stone

Man, the 90’s were a great time in country music. Alan Jackson was water-skiing in jeans, Tracy Byrd was doing the watermelon crawl, and Florida Georgia Line could only be found on a map and not on country radio. It was the best.

Obviously, everybody is still listening to “Chattahoochee” and “Friends in Low Places” and “Check Yes or No,” but there are some incredible songs that we were all listening to in the ’90s that may not get as much attention today as they should.

So here are some great country songs that you probably loved if you grew up in the ’90s, but you may have forgotten about.

“I’d be Better Off (In a Pine Box)” – Doug Stone

I firmly believe that this is one of the greatest country songs of all time.

Even as a little kid who didn’t know anything about love or feelings or any of that sh*t, I knew this song was a gut punch. And listening to it now…damn, this one will rip your heart right out.

“One Way Ticket” – LeAnn Rimes

LeAnn Rimes was one of the biggest artists of the late ’90s, despite the fact that she was only 13 when she released her first album. She was like the Mason Ramsey of the ’90s, but way less obnoxious and way more talented.

“Goodbye Says it All” – Blackhawk

The 90’s was a great time for country boy bands, but none of them had the harmonies down quite like Blackhawk.

“Trashy Women” – Confederate Railroad

Confederate Railroad’s cover of this Jerry Jeff Walker song gave it a southern rock edge. And if you’ve ever been to a shady dive bar on the rough side of town, you know exactly the kind of women they’re singing about.

“What Mattered Most” – Ty Herndon

Another great heartbreak song. Maybe the ’90s were more depressing than I remember them?

“Amy’s Back in Austin” – Little Texas

Another incredible country boy band from the ’90s.

“Love, Me” – Collin Raye

What I love most about ’90s country is the storytelling. Songs like this that can tell a story and take you through such a range of emotions in 3 minutes are what makes country so much better than other genres. Go ahead, try to change my mind.

“Bobbie Ann Mason” – Rick Trevino

Rick Trevino had so many heaters back in the day. Songs like “Learning As You Go,” “Running Out of Reasons to Run,” and of course, this ode to young love.

“Single White Female” – Chely Wright

This one really shows how much times have changed since the 90’s – if this song came out today, the guy would be swiping on Tinder instead of looking through the want ads in a newspaper. Still a great song though.

“Wine Into Water” – T. Graham Brown

This one was personal for T. Graham Brown, who struggled with the bottle even after he watched it take his friend Keith Whitley in 1989.

T. Graham has said that he didn’t want to record this song because he was still drinking at the time he wrote it, but decided to cut it anyway after some encouragement from his wife. Loretta Lynn even recorded a version for her 2016 album “Full Circle.”

“Down At The Twist and Shout” – Mary Chapin Carpenter

Not only is it impossible to sit still when this song comes on, but if you’ve never heard the live version performed at Super Bowl XXXI back in 1993 with legendary Cajun band BeauSoleil in New Orleans, it’s absolutely ELECTRIC when she hits that chorus in Cajun French.

“Tequila Talkin’” – Lonestar

A classic morning-after song about apologizing for the things you said while you were drunk – like telling your ex that you’re still in love with them. Dammit, Cuervo.

“Jacob’s Ladder” – Mark Wills

This debut single from Mark Wills about a young boy climbing into the window of his lover is still one of my favorite ’90s country songs.

“Jukebox Junkie” – Ken Mellons

Who doesn’t love rolling up to the dive bar and throwing some money in the jukebox to get the vibes right with your favorite country music? The driving sound on this one makes you want to run right to the closet bar and queue up some ’90s country.

“Blame It On Your Heart” – Patty Loveless

Patty Loveless is one of the most underrated artists of the ’90s, and she had so many hits that just absolutely took over back in the day – including this rockin’ heartbreaker.

“Sunday In The South” – Shenandoah

Talk about nostalgia. If you grew up in the ’90s, this one will take you right back to those lazy Sundays.

“Dumas Walker” – The Kentucky Headhunters

What’s a bottle of ski? Who knows, but this one will have you craving one. To be honest, the Dumas Walker sounds like just about the perfect dive bar, and the Kentucky Headhunters will have you ready to tie one on with this one.

“Down Came A Blackbird” – Lila McCann

Lila McCann seemed to be a superstar in the making after having hits with her first two singles, “Down Came a Blackbird” and “I Wanna Fall in Love,” at only 16. Unfortunately, she would only have one more song reach the top 10 in her career, but she managed to get this one stuck in everybody’s head at some point in the ’90s.

And if you’re itchin’ for some more 90’s country, you can find all these songs and more on our Saved By 90’s Country playlist on Spotify and Apple Music.


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Click here to shop the 90’s Country Collection in the Whiskey Riff Shop.


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A beer bottle on a dock



A beer bottle on a dock