Top 100 Saddest Country Songs about Death

Death is a subject that all folks must face. It is an inevitable part of life, and thus it has found its way into the hearts and minds of artists forever. The prospect of one’s inevitable expiration, the loss of another, or deaths that have occurred in conflicts and wars over the ages. Whatever the context, death has appeared in many art forms.

Country Music can be sad when it wants to be. And Country singers have never shied away from the subject of passing away. There are plenty of heartbreaking and heartwarming Country songs about death. 

So, I decided to take a closer look at the saddest Country songs about death, starting with…

Top 100 Saddest Country Songs about Death

1

He Stopped Loving Her Today By George Jones  

Album: I am What I Am

People have described George Jones as “The Rolls Royce of Country Music.” If that’s so, then this track has got to be the “Phantom” of Jones songs. 

Unreciprocated love is a bittersweet thing, and this track expressed that better than most. As with many country songs, the power of the story helps to capture the imagination of the listener. 

A young couple is parted, and the man refuses to let go of his love for her. He vows to love her until he dies. However, life goes on, and the two are not reunited despite his resolve. His friends attest to how he remained inconsolable after her departure and that he did indeed keep loving her. 

Eventually, he dies, and his former lover comes to pay her respects at his funeral…

The storyteller finally notes that now that she’s here, he is smiling for the first time in a long time. Despite this being the day, he could finally stop loving her. 

Countless surveys and publications have named this the greatest country song of all time. “He Stopped Loving Her Today” was selected for preservation in the Library of Congress in 2008. It was Jones’s first #1 hit as a solo artist, and one could argue that he never topped it. 

2

There You’ll Be by Faith Hill

Album: Pearl Harbour Original Soundtrack 

Celine Dion was originally offered this track. It was penned by Grammy award-winning songwriter Dianne Warren. And, while Dion liked it, she turned it down because she’d already done a massive ballad for a film soundtrack. 

Most will agree that Faith rose to the occasion with tremendous success. By this time, she had done plenty of ballads, some of which could have been considered crossover songs. But this track took it to another level. 

The arrangement isn’t as complex as some film pieces. But, the expert use of strings and percussion at the right moments helps to give Hill’s full-bodied voice the wings it needs to soar.

And, soar it does… 

The track’s appearance in the 2001 Michael Bay epic, Pearl Harbor, no doubt helped its popularity. But, one could equally argue that the track made the scenes in the film that much better. 

Remembering those who have passed on is how we keep their spirits alive. When we experience the pain of remembrance, we need to remind ourselves that to forget them would be to disgrace what they meant to us and still mean to us.

“There You’ll Be” became Faith’s highest charting single at the time of release and remains one of her most popular songs. 

3

Whiskey Lullaby by Brad Paisley (feat. Alison Krauss)

Album: Mud On The Tires

Whether it’s the writing, composition, the two beautiful voices, or the great production, there is little that doesn’t stand out on this double-platinum duet from Paisley’s third album. 

The song’s writer, Jon Randall, had gone through a divorce with country singer and actress Lorrie Morgan shortly before penning the song. On top of that, he had also lost a record deal and began drinking whiskey heavily. It got to the point where his manager and friend told him, “Hey man, every now and then, you’ve got to put a bottle to your head and pull the trigger.”

Randall decided to write this down, and “Whiskey Lullaby” was born. The story of a couple going through a difficult separation is told by the man (Paisly) during the first, with the women’s viewpoint following in the second. 

This song forces the listener to focus on the pain of the doomed lovers… 

The lyrics are given more stopping power by the acoustic guitar, dobro viola, and upright bass. All of them are seamlessly blended to make the perfect bed for the vocal to rest on. As a result, we get a sad Country Music song about dying.

“Whiskey Lullaby” won a CMA award for Song of the Year. It was Paisley’s eleventh charting single and even entered the Top 50 on the Billboard hot 100. The single has sold nearly two million copies. 

4

If Tomorrow Never Comes By Garth Brooks

Album: Garth Brooks

From Garth’s first album comes one of the saddest Country songs about death. Written with fellow country musician Kent Blazy, since its release, the track has become what many call Garth’s signature song. Brooks has since written many great Love songs. But, in many ways, this was his first venture into a love ballad. 

Talk about beginners’ luck, right? 

Lyrically, the track functions not only as a love ballad but as a straightforward contemplation of one’s demise. In many songs dealing with the subject of one’s death, the storyteller often thinks of the loved ones left behind first. This memorable Country song about death is no exception.

The protagonist in Garth’s story is battling his sleepless nights, filled with thoughts of angst and desperation. Not over the prospect of death but because his beloved might never know how much he cared about her.

This is a thought all of us will have at some point. And tracks like this can remind us to reach out to loved ones we haven’t connected with in a while before it’s too late. This multi-platinum track was Garth’s first #1 hit. 

5

I Drive Your Truck By Lee Brice 

Album: Hard 2 Love

This heart-wrenching slice of Country music was inspired by a radio interview that songwriter Corrie Harrington heard while driving in his car. In the interview, a local pastor spoke about his beloved son, who had recently lost his life in Afghanistan.

Losing a child is a burden that no parent should have to bear… 

To cope with the unimaginable grief of his son’s loss, this pastor would drive the young man’s truck to feel close to him. And Lee Brice’s performance of this story brought this story to life and touched the hearts of hundreds of thousands of Americas. 

Anyone who has lost someone dear can relate to the hollow feeling of not being able to get close to them ever again. Something as mundane as a truck or a jacket can become an almost religious vessel which allows you for some brief moments to believe that they are once more with you. “I Drive Your Truck” won Song of the Year at both the CMA and Academy Of Country Music Awards. 

6

Sissy’s Song By Alan Jackson

Album: Good Time

When we are struck with grief, the question we often ask is, “why so young and so sudden?” Especially if the person in question was kind and hardworking. This was the case when a woman who had been a housekeeper in Alan Jackson’s childhood home tragically passed in a motorcycle accident. 

Soon after the initial grief comes the problem of having to process it, and Jackson decided to do so by penning this beautiful track, containing all his thoughts and wishes for his dear “Sissy.” 

Using nothing but an acoustic guitar and Jackson’s voice, the track paints a vivid picture of Sissy. Even people who never saw her feel as though they could picture her in their minds as clearly as they can see their own hands. Jackson performed the song at Sissy’s funeral. 

7

Holes In The Floor Of Heaven By Steve Wariner 

Album: Burnin’ The Roadhouse Down 

This one will break you if you’re not ready, so don’t say I didn’t warn you. It comes from Steve’s thirteenth studio album and is one of the highlights of that great record.  

The protagonist of this tale starts by relating the pain he felt at the passing of his grandmother when he was eight years old. Despite her having only been there for the first few years of his life, he remembers her fondly. From there, the track deepens. We learn that years later, the man would have to endure the tragic passing of his young wife during the birth of their daughter. 

To endure this grief, the man uses the rain… 

When the rain comes down, he tells himself that it is the tears of his ancestors and loved ones raining down on him when they watch him experience moments of joy or sadness. “There’s holes in the floor of Heaven – and her tears are pouring down – That’s how I know she’s watching – wishing she could be here now.”

Luckily, Steve lets us off with a very pretty silver lining. At the end of this heartbreaking Country song about death, he describes how it started to rain shortly after his daughter’s wedding ceremony. “Holes In The Floor Of Heaven” won a CMA and ACM award for Song of the Year.

8

You Should Be Here By Cole Swindell 

Album: You Should Be Here

One thing that any young man dreams of is showing his father that he’s made something of himself in life and then sharing the joy of that achievement with their old man. 

Swindel left college in 2007 and moved to Nashville to try his hand at music. While doing other jobs, he started writing songs, and after three years of hard work, he was offered a publishing deal by Sony.  

His life changed, and he started writing and recording one hit song after another. He embarked on his first independent tour with fire in his heart, only to have it nearly snuffed out by the sudden and tragic passing of his father while he was away. 

Swindel decided to keep the spirit of his father alive in his music… 

Thus “You Should Be Here” was written. With an almost scathing passion, Cole expresses his anger and sadness and not having one of the people he cares about most with him to share in his success and happiness. 

Despite this, he knows that the last thing his father would have wanted would be for his son to stop playing music. “You Should Be Here” became Swidel’s fourth #1 on the County chart. It has been certified double-platinum and ranks among the saddest Country songs about death.

9

Go Rest High On That Mountain By Vince Gill

Album: When Love Finds You 

One of the most enduring and lovely Country songs about dying comes to us from Gill’s sixth studio album. Vince began writing this eulogy/ballad after he heard of the passing of fellow country musician Keith Whitley. He didn’t get around to finishing it until a few years later when his brother also passed away.

Despite being in a major key, Gill manages to imbue the song with such melancholy that it pulls on all the heartstrings at once. The fact that the deceased party is never named gives the track a beautiful ambiguity, and this allows for the theme to become very universal. 

When we lose a loved one, we are quick to think of our own grief. But, we eventually get around to realizing that what we want most for them is peace and rest. That’s what this beautiful song is all about. 

10

Three Wooden Crosses by Randy Travis

11

The House That Built Me by Miranda Lambert

12

Angels Among Us by Alabama

13

If You’re Reading This by Tim McGraw

14

One More Day by Diamond Rio

15

If Heaven Wasn’t So Far Away by Justin Moore

16

Why by Rascal Flatts

17

Live Like You Were Dying by Tim McGraw

18

Love, Me by Collin Raye

19

When I Get Where I’m Going by Brad Paisley (feat. Dolly Parton)

20

A Picture of Me (Without You) by George Jones

21

Travelin’ Soldier by Dixie Chicks

22

The Baby by Blake Shelton

23

I Can Still Make Cheyenne by George Strait

24

Highway 20 Ride by Zac Brown Band

25

I Will Always Love You by Dolly Parton

26

Tear In My Beer by Hank Williams Jr. (feat. Hank Williams)

27

When You Say Nothing At All by Alison Krauss

28

You’ll Never Leave Harlan Alive by Brad Paisley

29

Mama Tried by Merle Haggard

30

Like We Never Loved At All by Faith Hill (feat. Tim McGraw)

31

The Best Day by Taylor Swift

32

The Good Die Young by Billy Joel (feat. LeAnn Rimes)

33

Coat of Many Colors by Dolly Parton

34

I’ll Fly Away by Alison Krauss and Gillian Welch

35

You Can Let Go by Crystal Shawanda

36

You Should’ve Seen It In Color by Jamey Johnson

37

Old Friends by Willie Nelson

38

He Ain’t Heavy, He’s My Brother by Don Reid and Harold Reid

39

Why Me Lord? by Kris Kristofferson

40

Wherever You Are by Terry Clark

41

That’s Why God Made Mexico by Tim McGraw

42

My Front Porch Looking In by Lonestar

43

You Can Let Go Now Daddy by Crystal Shawanda

44

Stay by Sugarland.

45

When I Get Where I’m Going by Brad Paisley and Dolly Parton

46

Arlington by Trace Adkins

47

Raining on Sunday by Keith Urban

48

I’ll Fly Away by Alison Krauss and Gillian Welch

49

The Last Cowboy Song by Ed Bruce

50

Traveller by Chris Stapleton

51. 51. The Dance by Garth Brooks
    52. Drink a Beer by Luke Bryan
    53. Don’t Blink by Kenny Chesney
    54. Goodbye Time by Blake Shelton
    55. You Can’t Take It with You When You Go by The Mavericks
    56. I’m No Stranger to the Rain by Keith Whitley
    57. Goodbye Earl by Dixie Chicks
    58. The Little Girl by John Michael Montgomery
    59. Family Tree by Darryl Worley
    60. Heaven Was Needing a Hero by Jo Dee Messina
    61. See You Again by Carrie Underwood
    62. Just A Dream by Carrie Underwood
    63. There’s a New Kid In Town by Keith Whitley
    64. Tell Lorrie I Love Her by Keith Whitley
    65. I Will Remember You by Sarah McLachlan
    66. I’ll Be Missing You by Puff Daddy (feat. Faith Evans & 112)
    67. You Shouldn’t Have to Love Me by Keith Urban
    68. How Can I Help You Say Goodbye by Patty Loveless
    69. If I Had Only Known by Reba McEntire
    70. Forever and Ever, Amen by Randy Travis
    71. The Last Day of My Life by Phil Vassar
    72. I Can’t Stop Loving You by Ray Charles
    73. Daddy’s Hands by Holly Dunn
    74. Believe by Brooks & Dunn
    75. There’s a Hero by Billy Gilman
    76. That’s My Job by Conway Twitty
    77. Love Like Crazy by Lee Brice
    78. There Goes My Life by Kenny Chesney
    79. I Hope You Dance by Lee Ann Womack
    80. Holes in the Floor of Heaven by Steve Wariner
    81. Everybody Hurts by R.E.M. (covered by country artists)
    82. Who You’d Be Today by Kenny Chesney
    83. Tougher Than the Rest by Chris LeDoux
    84. It’s Five O’Clock Somewhere by Alan Jackson and Jimmy Buffett
    85. The Grand Tour by George Jones
    86. Blue by LeAnn Rimes
    87. If I Die Young by The Band Perry
    88. Somewhere in My Broken Heart by Billy Dean
    89. I’m Already There by Lonestar
    90. The Ride by David Allan Coe
    91. Go Rest High on That Mountain by Vince Gill (previously mentioned, but worth repeating)
    92. There’s a Place in the World for a Gambler by Dan Fogelberg
    93. Singer in a Cowboy Band by Marty Robbins
    94. Streets of Heaven by Sherrie Austin
    95. Bless the Broken Road by Rascal Flatts
    96. Don’t Take the Girl by Tim McGraw
    97. I’m No Stranger to the Rain by Keith Whitley
    98. Wildfire by Michael Martin Murphey
    99. Dust in the Wind by Kansas (covered by Kansas native, Dolly Parton)
    100. I Can Only Imagine by MercyMe (covered by multiple country artists)

Looking for More Great Country Music?

Well, check out our thoughts on the Best 90s Country Songs, the Best Country Love Songs, the Most Famous Male Country Singers Of The 1970s, the Most Famous Female Country Singers Of All Time, the Saddest Rock Songs, and the Best Sad Songs for more emotionally-charged song selections.

Saddest Country Songs about Death – Final Thoughts

Death is never a pleasant thing to deal with, but all of us are bound to face it a few times during our lives. It’s good to know that there are endearing and heartfelt songs like these sad Country songs about death to help us process our grief and feel less alone in times of loss.

So, until next time, let the music play.