11 Heartbreaking Country Songs About Grief & Loss

(Left) BRADPAISLEY / YouTube / (Center) Vince Gill / YouTube / (Right) Miranda Lambert / YouTube

Music can be healing. So it’s no wonder why people find comfort in music during times of stress, worry, or heartache.

Country music artists and songwriters often channel these feelings into their work. That’s how we end up with some heartbreakingly relatable songs about tough subjects such as grief and loss.

It’s unfortunate that many of the most devastating country songs were written from a place of personal experience. For example, Vince Gill penned “Go Rest High on That Mountain” following the death of his brother. Cole Swindell‘s “You Should Be Here” is about the loss of his father.

Those are just two of the 11 songs we have featured in this list. All of these songs cover the subject of grief in different ways. They’re all emotional, so be sure to keep some tissues close as you make your way through the list.

And to those whose own lives sadly mirror one or some of these songs, our hearts go out to you…

“The Father, My Son and the Holy Ghost”

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Craig Morgan released “The Father, My Son and The Holy Ghost” in 2019. The song is about the grief he experienced following the death of his son, Jerry, in 2016. Jerry was only 19 years old at the time of his death.

One of the lines is, “I know my boy ain’t here but he ain’t gone.”

“Over You”

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Blake Shelton was inspired to write “Over You” after losing his big brother, Richie. Blake was just 14 when Richie was killed in a car accident.

Shelton co-wrote “Over You” with his then-wife, Miranda Lambert. Shelton didn’t know if he’d have the strength to record the song, so he gave it to her to sing.

Some of the most heartbreaking lyrics are in the chorus, when Lambert sings, “But you went away. How dare you? I miss you.”

“Whiskey Lullaby”

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“Whiskey Lullaby” is a song about loss in two ways: romantically and through death. It was co-written by Bill Anderson and Jon Randall.

Randall was going through a hard time in life when his manager told him, “Hey man, every now and then you’ve got to put a bottle to your head and pull the trigger.” He then brought up that line when he and Anderson wrote “Whiskey Lullaby.”

The song tells the story of two lovers who have since parted ways. The man drinks himself to death, and the woman soon follows him, as the grief and heartache becomes too much for her to cope with.

Brad Paisley immediately expressed interest in the song. He wanted to record it with Alison Krauss as a duet, and that’s exactly what happened. They ended up creating one of the saddest country songs of all time.

“I Drive Your Truck”

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Jessi Alexander, Connie Harrington, and Jimmy Yeary co-wrote “I Drive Your Truck,” and Lee Brice recorded it.

Harrington was inspired to write the song after hearing a story on the radio program Here and Now. A father named Paul Monti spoke about his son, Medal of Honor recipient Jared Monti, who was killed in Afghanistan while trying to save another soldier. During his interview on Here and Now, Paul said he drove his son’s old truck whenever he wanted to feel close to him.

It’s hard not to tear up throughout all of “I Drive Your Truck,” especially when Brice sings, “Momma asked me this morning if I’d been by your grave. But that flag and stone ain’t where I feel you anyway.”

“You Should Be Here”

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As mentioned previously, Cole Swindell felt inspired to write “You Should Be Here” following his father’s unexpected death in 2013. He co-wrote the song with Ashley Gorley, and released it in 2015.

The chorus packs on the emotion, as Swindell sings, “And you know that if I had just one wish it’d be that you didn’t have to miss this. You should be here.”

“Go Rest High on That Mountain”

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Vince Gill first started writing “Go Rest High on That Mountain” following the death of Keith Whitley in 1989. He finished the song years later after his older brother, Bob, died of a heart attack.

Ricky Skaggs and Patty Loveless joined Gill as the backing vocalists on the recording.

In the years since “Go Rest High” was released, Gill has performed the song to honor many artists who have passed away. One of the most memorable live performances was at George Jones‘ funeral service in 2013.

“Maggie’s Song”

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Chris Stapleton‘s “Maggie’s Song” is a slightly different song about grief. It’s about the loss of a pet, specifically the Stapleton family’s beloved dog, Maggie.

Anyone who’s ever loved and lost a four-legged companion will find themselves in tears as they listen to Stapleton sing, “She put her head on my hand, like she’d done so many times. I told her she was a good dog, then I told her goodbye.”

“See You Again”

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Carrie Underwood co-wrote “See You Again” with Hillary Lindsey and David Hodges. In the song, Underwood speaks about how she’ll one day be reunited with her loved ones in heaven.

Underwood once told Audacy:

It’s not the end. In my mind, in my faith and what I believe, there is a heaven. There is a God and we’re going to be there someday. It’s of course very sad to lose somebody here on Earth, but having that faith and knowing that you’re going to see them again is such an amazing thing, such a comforting thing, such a happy thing. That’s what the song is all about.”

“One More Day”

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Bobby Tomberlin and Steven Dale Jones co-wrote “One More Day,” which was recorded by Diamond Rio. As the chorus goes:

“One more day, one more time. One more sunset, maybe I’d be satisfied. But then again, I know what it would do. Leave me wishing still, for one more day with you.”

“One More Day” gained popularity following Dale Earnhardt’s death in February 2001. The song was also played a lot following the 9/11 attacks, and was used in tributes to the victims.

“Five More Minutes”

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Scotty McCreery co-wrote “Five More Minutes” with Frank Rogers and Monty Criswell. McCreery wrote the song following his grandfather’s death in 2015. The song expresses how he wishes he could spend five more minutes with his beloved grandpa.

As he sings, “All the family gathered ’round knew the time was coming soon. With so much left to say I prayed Lord I ain’t finished. Just give us five more minutes.”

“Holes in the Floor of Heaven”

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Steve Wariner co-wrote “Holes in the Floor of Heaven” with Billy Kirsch. The heartbreaking song tells the story of a man who’s experienced a lot of loss in life.

The narrator first sings about his grandmother’s death when he was a young boy. At that time, his mom told him not to be sad, and to think of the rain falling as being tears from his loved ones in heaven.

As the chorus goes:

“Cause there’s holes in the floor of heaven, and her tears are pouring down. That’s how you know she’s watching, wishing she could be here now.”

Later, the man loses his young wife in childbirth. On the day of their daughter’s wedding, it rains, and she reminds him not to be sad, repeating the same words about the rain being tears from heaven.

Watch Wariner perform a live rendition of “Holes in the Floor of Heaven” below. It’s a heartbreakingly beautiful song, as are all of the songs in this list.

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