I Ranked the Saddest Country Songs Ever Written—Here’s the One That Ruined Me

Country music is known for being sad. It’s the genre of heartbreak, thanks to country’s unparalleled excellence for storytelling and emotionality. Every country fan—even those who have only dipped their toe in—knows the somber lean that this genre tends to take. I, too, thought I knew all that sad country music had to offer, until I revisited some of the most devastating. The four country songs below are all really beautiful bummers, with the final entry being the one that ruined me the most.

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“Travelin’ Soldier” — The Chicks

Several people have recorded “Travelin’ Soldier.” Each time this song is redone, we’re reminded just how painful it is. The Chicks made this song famous, breaking our hearts with their tender harmonies. This story of a young couple separated by war is almost too much to bear. By the time the kicker is revealed in the bridge, the listener’s eyes are all ready welled up.

The only place this song falls short of being universally the saddest country song ever is the fact that not everyone can personally relate. Of course, this song will hit home for some, but many country fans see it only through sympathetic eyes.

“Whiskey Lullaby” — Brad Paisley & Alison Krauss

“Whiskey Lullaby” is a story of lost love that sears the listener to the bone. While there are many country breakup songs, none sting quite the same as this one.

Brad Paisley and Alison Krauss take on the dual perspectives in this song, throwing salt in the listener’s wounds at every turn.

“Hurt” — Johnny Cash

[RELATED: Remember When Johnny Cash Played a Frat House, Went to Jail, and Wrote a Prison Song About It?]

The runner-up to the saddest country song of all time would have to be Johnny Cash’s “Hurt.” While the lyrical content of this Nine Inch Nails cover is somber, Cash’s pained delivery only makes it that much more so.

You can hear Cash’s age in his rendition of this song, giving it an existential edge. Cash fully lives the lyrics he’s singing, pulling the listener down in the dumps with him.

“Go Rest High On That Mountain” — Vince Gill

Sometimes it’s the simplest of messages that cuts the deepest. Take Vince Gill’s “Go Rest High On That Mountain” for example. This song isn’t anything complex or uber specific, but that’s what makes it the most universal message of grief in country music.

There are many topics that can make a country song sad—heartbreak, nostalgia, or anecdotal tales. But, if there’s one idea that manages to hit everyone the hardest, it’s grief. Gill laid bare his emotions on “Go Rest High On That Mountain,” completely shattering anyone who listens to this song. Though there is stiff competition, this Gill classic is a pretty good contender for the saddest country song of all time.

(Photo by Al Clayton/Getty Images).