Ten 90’s Country Songs That You Loved But Probably Forgot About

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 AJ McLean was a Backstreet Boy and not a country artist. It was the best.

As I was listening to Jillian Jacqueline talk about some of her favorite 90’s country artists on a recent episode of Whiskey Riff Raff, it reminded me of some of the songs I loved back in the 90’s but have since forgotten about. Probably because back then the only way to listen to them was on the radio or a cassette – because nobody could afford those massive CD players yet.

Obviously, everybody is still listening to “Friends in Low Places” and “Check Yes or No,” but here are 10 great country songs that you probably loved if you grew up in the 90’s, but you may have forgotten about.

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

Even as a little kid who didn’t know anything about love or feelings or any of that shit, 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 90’s, despite the fact that she was only 13 when she released her first album. She was like the Mason Ramsey of the 90’s, 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 90’s were more depressing than I remember them?

“Love, Me” – Collin Raye

What I love most about 90’s 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

Ah, young love. This one will take you back to high school when the most important thing wasn’t whatever the teacher was talking about in algebra that you would never use again…it was that girl sitting in front of you that you couldn’t stop staring at.

“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.”

“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.

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