3 Gut-Wrenching Country Songs From the 1990s You Can Barely Make It Through

There was plenty of sadness to go around in the 1990s. While grunge and alternative rock made anthems out of misery, country music offered gut-wrenching songs in a genre known for emotionally painful themes. Country songwriters not only dialed up the anguish, but the singers also recorded moving performances, leaving many listeners in tears. But music helps us through grief, too. Often, a sad song is exactly what one needs when they just want to curl up and cry. Hard!

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If there’s such a thing as a Sad Song Hall of Fame, these tracks certainly deserve to be inducted. But keep the tissues handy while you give these three gut-wrenching country tunes a spin. You’re going to need them.

“Go Rest High On That Mountain” by Vince Gill

Vince Gill spent years writing, hurting, and perfecting his funeral song. The death of singer Keith Whitley had inspired the initial idea. But it wasn’t until Gill’s older brother passed away that he finally completed what ultimately became a hymn more than a country ballad. Gill croons one of the saddest country songs of the decade, and good luck to anyone tasked with eulogizing a loved one with this weeping tune.

“You Were Mine” by The Chicks

“You Were Mine” describes a broken marriage and an ex who has moved on to a new relationship. Meanwhile, his wife remains in despair, staring at old wedding photos and screaming her ex-husband’s name in the middle of the night. But the song reaches its gut-wrenching phase when Natalie Maines mentions the couple’s two children, ages two and four, and wonders how she’ll explain their father’s absence to them. The hit appears on The Chicks’ breakthrough album, Wide Open Spaces, which also marked Maines’s first with the group.

“Sweet Old World” by Lucinda Williams

“Sweet Old World” finds Lucinda Williams writing about one who has committed suicide. She lists simple things we take for granted: a breath, a touch, a kiss, and the sound of a train. But the common experiences are profound once they are gone. Her easy tune moves along at a steady pace, like the rest of life continuing after a tragedy that’s hard to reconcile. There is no “why” or “how come” to satisfy family and friends searching for explanations. Instead, we are left with a long list of reasons for “why not” and “don’t”. But it’s too late, and that makes Williams’s song so gut-wrenching.

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