The List

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

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. Letโ€™s take a look!

โ€œStrawberry Wineโ€ by Deana Carter from โ€˜Did I Shave My Legs For This?โ€™ (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. Thereโ€™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.

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โ€œStrawberry Wineโ€ 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.

โ€œWhat Might Have Beenโ€ by Little Texas from โ€˜Big Timeโ€™ (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 โ€œWhat Might Have Beenโ€ by Little Texas, and even non-fans of country loved it.

โ€œWhat Might Have Beenโ€ 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.

โ€œThe Foolโ€ by Lee Ann Womack from โ€˜Lee Ann Womackโ€™ (1997)

Remember this gem from Lee Ann Womack? โ€œThe Foolโ€ 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. Itโ€™s a pretty vulnerable song, one that ended up becoming a hit for Womack in 1997.

โ€œThe Foolโ€ peaked at No. 2 on the Hot Country Songs chart nd No. 5 on the Canada Country Singles chart.

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