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3 Country Ballads From the 90s That Made Small-Town Heartbreak Feel Relatable to City Folks

By Em Casalena Nov 2, 2026 | 7:00 AM
Lee Ann Womack at the Chicago Country Music Festival on 7/01/01 in Chicago, Il. (Paul Natkin/Image Direct)

Some country ballads released in the 90s were so good that even non-country fans and city folks adored them. It was the era of country-pop taking over the airwaves, after all. And even if you never grew up in a small town, the following three country ballads from the 90s likely made you feel nostalgic for an experience you never actually had. Let’s take a look!

“Strawberry Wine” by Deana Carter from ‘Did I Shave My Legs For This?’ (1996)

This song was the small-town heartbreak ballad of the 90s. Deana Carter croons about being a teen in love during the summer, only for that romance to be a fond yet bittersweet memory decades later. There’s also this overarching theme of returning to a place that has changed significantly years later. And many a small-town kid likely related to this song quite a bit.

“Strawberry Wine” by Deana Carter was a No. 1 hit on both main country charts in the US and Canada. It was close to being a pop success, too, reaching No. 65 on the Billboard Hot 100 chart.

“What Might Have Been” by Little Texas from ‘Big Time’ (1993)

Anyone who grew up in a small town and fell in love, only for that relationship to not last, likely reminisces at times about what could have been. Heck, if you grew up in the city, you might occasionally look back at your first love in a similar way. That wistfulness is captured in “What Might Have Been” by Little Texas, and even non-fans of country loved it.

“What Might Have Been” by Little Texas was a No. 2 hit on the Hot Country Songs chart and also crossed over to the Adult Contemporary chart at No. 16 back in 1993.

“The Fool” by Lee Ann Womack from ‘Lee Ann Womack’ (1997)

Remember this gem from Lee Ann Womack? “The Fool” was a real country drama back in 1997, and it had a light touch of pop to it that made the song popular among city folks, too. It’s a pretty vulnerable song, one that ended up becoming a hit for Womack in 1997.

“The Fool” peaked at No. 2 on the Hot Country Songs chart nd No. 5 on the Canada Country Singles chart.

Photo by Paul Natkin/WireImage

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