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The Outlaw Pat Garrett’s Top 5 Saddest Country Songs

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#5. George Jones, “He Stopped Loving Her Today”

Many of the all-time saddest songs in country music are either about heartbreak or about death: This one is about both. He Stopped Loving Her Today” is about a man whose life is defined by the woman he lost.

#4. Hank Williams, “I’m So Lonely I Could Cry”

In 1949, “I’m So Lonesome I Could Cry” was released as a melancholy counterpoint to more upbeat Williams hits like “My Bucket’s Got a Hole in It.” With its chilling wail and plaintive fiddle solo, really brings it home.

#3. Garth Brooks, “The Dance”

1990 smash-hit “The Dance” has a double meaning. On the one hand, it’s one of the country genre’s most powerful songs about love lost. You can interpret as a song that accepts the pain of heartbreak as the price you pay for true love.

#2. Dolly Parton, “I Will Always Love You”

Released in 1974 as a farewell message to her mentor and boss Porter Wagoner, and it’s plaintive, iconic melody perfectly sums up the heartbreak of saying goodbye to someone important, even though both parties know it’s for the best.

#1: Vince Gill, “Go Rest High on That Mountain”

Go Rest High on That Mountain” has become such a frequently reached-for musical choice for memorials and funeral services: It’s a powerful, pure song that speaks to the pain of losing a loved one and the comfort of knowing that they are safely in heaven.

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