The Saddest Country Songs of All Time – Part 5

And we conclude with the final ten sad country songs…

Sad Country Songs Part 5

10) Concrete Angel – Martina McBride

Martina McBrideMartina McBride has always been one of the best country singers of all time. She is also known for putting out songs that pull at the heartstrings while making people aware of difficult topics. At the end of 2002 Martina released the song Concrete Angel as the final single from her Greatest Hits album. The song was about an abused little girl that can’t get away from her parents that keep abusing her. Finally the little girl doesn’t make it any longer and she makes her way to the after life. The song is heartfelt and extremely sad. Neighbors in the story turn their heads the other way not knowing what to do. Even though some situations in life make us uneasy we need to acknowledge they exist and make the world the best place for our family and friends as we can. Thanks Martina.

9) Love Me – Collin Raye

Collin Raye became a country superstar in the early ’90s after his second single effort Love, Me made it all the way to the top of the country charts in 1991. The song is a story about a couple that fell in love many years ago. Throughout the couple’s life they left each other notes and always ended them with the salutation Love, Me. The song is a beautiful story about how love can withstand all the pressures life can throw at it. Don’t give up and keep fighting for the one you love. If it’s really true love you won’t be let down. Even when one of you passes away don’t worry. If you believe you will find a way to be together once again. Collin Raye would go on to have many more hits over the next decade but it was that first big hit that made him a star and still remains his signature song today.

8) The Walk – Sawyer Brown

Sawyer BrownBy the end of 1991 country superband Sawyer Brown seemed to be on the downside of their career. Their last few singles in the late ’80s had floundered near the far ends of the country charts and the band was in need of a hit. The song that brought the guys back into relevance was The Walk. The ballad tells the story of a father and son. The story starts out with the young boy being afraid to get on the bus for school. The dad consoles the little guy by telling him their is nothing to worry about – “I took the same walk with my old man. I’ve been in your shoes.” The story continues through live and eventually the two wind up at the bedside as the dad is passing away. The dad assures his son that everything will be alright because he’s taken this walk with his own father. It’s always nice to hear stories of difficult situations others have gone through. We can all picture ourselves in the same situations and if we’re going through a tough situation our self a song like The Walk can help us get through. The tune turned Sawyer Brown’s career around and they went on to have tons of hits in the ’90s.

7) Live Like You Were Dying – Tim McGraw

Tim McGrawIn 2004, country superstar Tim McGraw was dealing with the death of his father. Just a few months before the song Live Like You Were Dying was released Tim lost his father, baseball player Tug McGraw to complications of a brain tumor. Tim didn’t know that his father was Tug until later in life and it took a long while before they even became friends. Toward the end of Tug’s life they seemed to become great friends as well as being father and son. The message of the song is to live life to the fullest each day. You never know how many days you’ll have left to live so make the most of it. Love those around you and do the things that make you happy. Live a full like just as if you knew you were dying. Not many of us actually live this way even though we all know we’ll one day die. Maybe we can make that change today.

6) I Don’t Call Him Daddy – Doug Supernaw

Doug Supernaw became a country star with the release of his third single I Don’t Call Him Daddy. The song became Doug’s lone number one hit on the country charts. I Don’t Call Him Daddy is a story about divorce and the kids that get caught up in the middle. The narrator of the song calls up his young son to chat and they talk about everything including the new man in the boy’s mom’s life. They boy says that the guy is nice enough, but he’ll never take the place of his real dad. There is a strong love between a father and son. Many kids grow up wanting to be just like their dads. Divorce is a difficult situation to go through and when the parents move on it can be confusing for the kids and for the new parents. Kids always seem to make the best of the situation while realizing that nobody can ever take the place of their parents – blood or love.

5) Seven Spanish Angels – Ray Charles and Willie Nelson

Ray Charles and Willie Nelson recorded one of the greatest and saddest country songs of all time in 1985. The song was Seven Spanish Angels and it went on to reach the top spot on the charts. It was a monster hit for both Ray and Willie. The song is the story of a young couple. The man is in a fight for his life and as he sits and chats with his lover he realizes that he probably won’t make it out of the fight alive. The guns banged and the smoke fills the air. When the smoke clears the woman realizes that her lover is gone. She tries to take her own life because she can’t live without her man. Her prayers are answered when the rifles continue to bang away. The smoke clears and she joins him at home. It’s a sad song about a love that moves on from this life. The vocals Willie and Ray put on the track is beautiful and perhaps one of the greatest moments in country music. It truly is the artists that made this song great.

4) Wish You Were Here – Mark Wills

In 1999, country singer Mark Wills had a huge #1 hit with the tearful ballad Wish You Were Here. The song captured the hearts of many as it pulled at the emotions of each listener. The song is a story of a young couple that has to part ways for a bit. They say goodbye at the airport terminal gate. The guy buys a postcard that says “Heaven” on the front and he plans on sending it to the one he loves. She heads home and gets a call later expecting it to be him. She breaks down and hears that the plane has crashed – no survivors. Someone later on the mail she gets the postcard that says “Heaven” on the front. She reads that her loved one wishes she was there. It’s beautiful and that he wishes he could hold her close and see the wonders he sees. This song is enough to make just about anybody have a good cry.

3) What Hurts The Most – Rascal Flatts

Rascal FlattsIn 2006, country superstars Rascal Flatts released what is perhaps their biggest single. What Hurts The Most is a song about love lost and how much it hurts when you lose someone. It can be through breakup, death, or any other reason. It usually doesn’t matter what the cause is. What matters is that it hurts more than anything else in the world. It hurts being so close to someone and then losing that love and everything that goes along with it all in an instant. The song became a top hit on the country charts and even peaked in the top ten on the pop charts. Songs like What Hurts The Most make some sad and emotional, but these are the songs that help us cope with the loss of someone we love so much. We needs these songs in country music. They’re therapy.

2) He Stopped Loving Her Today – George Jones

George Jones was down and out by the time 1980 rolled around. The country legend was looking for a major hit to bring him back to superstardom. That song came in the form of He Stopped Loving Her Today. The song is often regarded as the best country song of all time. It’s a song about a guy that simply can’t get over the love he has for his woman. She left him and figures he’ll get over her, but he just can’t. Nothing ever comes between his love and nothing can ever make him stop loving her. The song ends with the final conclusion that he finally stopped loving her but it was in fact his death that finally ended the love. George puts the perfect vocal on the song. His emotional and soulful voice wains and cries through the lyrics. George Jones is country royalty because he can sing a song like no other. He Stopped Loving Her Today is the perfect definition of country music. It’s sad. It’s beautiful. And most important it’s country.

1) Go Rest High On That Mountain – Vince Gill

Vince Gill’s career is filled with many heartfelt ballads and sad country songs that tear out every last bit of emotion from your heart. In 1995 the singer released what is perhaps his biggest signature hit with Go Rest High On That Mountain. The song started out as a tribute to the late Keith Whitley yet Vince didn’t finish the song until his own brother died in the early ’90s of a heart attack. Go Rest High On That Mountain serves as a beautiful tribute to anyone that has died as well as giving a bit of understanding and hope for friends and family left back to grieve. All of us will go through the loss of more than just a few people in our lives and it’s never easy. Songs like Vince Gill’s Go Rest High On That Mountain may be sad songs but they truly help others understand why things happen in life. That kind of impact is what makes for one of the greatest country songs of all time. Thanks Vince for helping us all deal with the loss of loved ones.

Entire List

The Saddest Country Songs of All Time

The Saddest Country Songs of All Time Part 2

The Saddest Country Songs of All Time Part 3

The Saddest Country Songs of All Time Part 4

17 More Sad Country Songs

Dayne Shuda

Founder of Country Music Life. Follow on Twitter: @dayneshuda Follow on Google+: Dayne Shuda

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  1. Stephanie Johnson says

    Leann Rimes “Probably wouldn’t be this way” should have made it, I cry every time I hear it!

  2. says

    Ooo. That’s another good one, Stephanie. That’s a powerful song. I may have forgotten it since it’s fairly recent, but it certainly is a sad country song.

  3. l0rd0ct0d0rk says

    All good songs, but Dwight Yoakam’s “I sang dixie (as he died)” deserves honorable mention, as well as a few others.

  4. Stephanie says

    I agree on all of these! I wish there was a longer list. I think George Strait’s “Today My World Slipped Away” is so sad.

  5. Stephanie says

    Don’t forget
    Lorrie Morgan “If You Came Back From Heaven” or “Dear Me”
    Reba McIntyre “The Last One To Know”

  6. says

    On my list of to-do’s are these songs. There needs to be another sad sons post kind of like how George Stait released his 22 More Hits CD.

  7. Will says

    “Almost Home” by Craig Morgan,”Raymond” by Brett Eldredge, “Sissys Song” by Alan Jackson

  8. Janie says

    Can someone tell me the name of a song I heard a couple of times by Kenny (dont know his last name). He wrote the song just before he died. It was from the heart, of the heart or something like that. Cant find it anywhere but it was the best I ever heard. Thanks

  9. Corey says

    New additon to the list. Jusy My two cents but I always thought Ghost in this House by Shenandoah was one of the saddest songs i ever heard. Thanks

  10. Claude says

    sorry dane..your list doesn’t cut it with real country singers except hank and george…no gary stewart on your list, any of gary’s tunes would beat any of the “new” country artists any day.

  11. Wade says

    what a pathetic list, the only good songs on here are Hank Williams’s Your Cheatin’ Heart and Ray Charles and Willie Nelson’s Seven Spanish Angels, the rest are just sappy pathetic attempt’s at sad songs. Where is Marty Ribbins, Bobby Bare, and Hank Snow.

  12. Jason says

    I wasnt impressed by most of the list. “I’m so lonesome I could cry”, the saddest song i’ve ever heard. They did miss a lot of good songs, especially the good songs by the older singers of the 50’s-80’s. Conway, George, Marty, Jerry Lee, Keith, Dwight, Merle, Elvis, and so many more.

  13. Luke says

    I’m surprised by some of the songs on here…what about Gary Stewart’s “An Empty Glass” or Keith Whitley’s “Between An Old Memory and Me” or I Never Go Around Mirrors.” I think you have a good list, but when it comes to sad country songs, you left some great oldies off of there.

  14. Purslet says

    Im gonna try to be as nice as possible… Toby keith or rascal flats should never ever EVER!!! Be put in front of hank williams. “alone and foresaken” “my son calls another man daddy”. Todays commercial mainstream country nashvile fasion show is nothing compared to real country music, it went with the opry. Seven spainish angels is suuuuchh a good song tho and I agree with you on that one, ray charles did so much for country music.

  15. Kavin Caruso says

    you forgot the 1985 Charly McClain song. “Radio Heart”, that’s a good sad song. another one would be Colin Raye 1994 top hit, “Little Rock”,also 2008, Kenny and Reba, “Every Other Weekend”

  16. Daryl Collison says


    I am trying to find a song I remember hearing not that long ago. It is about a man who keeps putting things off – he will take care of something later. Then time goes by and eventually he gets cancer. I cannot remember the name of the song, I thought it might be on your Top 50 list. Does this ring any bells for you? I am going to try a YouTube sad country song search and see what happens.

    Thanks in advance for any assistance.

  17. Jose Ahumada says

    After getting better acquainted with country music over the past year (after I became a truck driver) I think this is the only list that even mentions songs like “Seven Spanish Angels” and “Go Rest High on that Mountain”. Those songs are beautiful and just wrench your heart, especially “Go Rest High..” after watching Vince Gill and Patty Loveless perform it at George Jones’s memorial.

    “Long Black Limousine” is a song I find hard to get through without choking up a bit.

  18. Micah says

    Now some of these songs I have not heard butt, I think the sadest song I have ever heard is saving Amy by Brantley Gilbert

  19. Tom says

    Long Black Veil by Lefty Frizell, Randy Travis has several that could make this list, Whiskey Lullaby is noticeably absent, and there are a few songs on this list that really aren’t sad songs if you listen to them.

  20. Veto Roley says

    Several songs come to mind and one (“Chiseled in Stone” by Vern Gosdin) you have on your 17 additional saddest songs list. However, I would add these songs (and, I love sad country songs, so please excuse the length):

    “I’m So Lonesome I Could Cry” — Hank Williams just makes time stand still here…

    “Standing in the Shadows” — must have been very hard to be Hank’s son and told he was not as good as his dad…

    “Down from Dover” — Saddest song in Dolly Parton’s inventory… young girl gets pregnant, parents kick her out and child is stillborn

    My body aches, the time is here; it’s lonely in this place where I’m lyin’

    Our baby has been born but something’s wrong — it’s much too still, I hear no cryin’

    I guess in some strange way she knew she’d never have a father’s arms to hold her

    And dying was her way of telling me he wasn’t coming down from Dover

    “Maggie’s Never had a Love” — Don Williams, sad to be looking for that someone and rationalizing why it never happened…

    “Cat’s in the Cradle” — Ricky Skaggs, but same version as Cat Stevens… “My son grew up to be like me…”

    “Those Memories of You” by Trio (Dolly Parton, Emmylou Harris, Linda Ronstadt)

    “She’s Got You” — Patsy Cline

    “Help Me Make it Through the Night” — Sammi Smith

    “For the Good Times” — Ray Price

    “You Gave Me a Mountain” — Marty Robbins — wonder how the guy lived through all the disaster…

    “Life of the Party” — Randy Travis sung this one on the t.v. series Matlock, probably his best song ever…

    “He Walked All the Way Home” — Larry Sparks about the end of the Civil War and a Confederate soldier walking back home with the dead on his mind…

    “This Is the Last Time You’ll See Jenny” — McPeak Brothers; man goes off to the Civil War and comes back in a casket…

    “Turn the Wine Back into Water” — T. Graham Brown, about an alcoholic reminding Jesus He turned water into wine, can’t He turn wine into water…

    “More than a Name on a Wall” — Statler Brothers — a mother remembers her son who was killed in Vietnam…

    “In the Ghetto” — Mac Davis and Elvis do good on this song, but Dolly Parton’s version will rip your heart out…

    “Yesterday When I Was Young” — Roy Clark… the regrets of youth

    “Take My Hand Precious Lord” — Tommy Dorsey/Multiple; Tommy Dorsey wrote this after losing his wife while giving birth to their son. Their son died the next day.

    “I Was Almost Home” — Craig Morgan, man wakes up a homeless man who was about to die and the homeless man says he was almost home…

    “A Good Year for the Roses” George Jones — as his wife leaves, all he can think about is that it’s been a good year for the roses.

    “Grand Tour” — George Jones or Aaron Neville

    “You’ll Never Leave Harlan Alive” — Patty Loveless

    “She’s a Lady” — Alabama

    “Broken Lady” — Larry Gatlin

    “Beneath Still Waters” — Osburn Brothers or Emmylou Harris

    “Ode to Billy Joe” — Bobby Gentry does it extremely well, but the backup singer in Ray Charles’ band hits it out of the park.

    “Thirty Nine and Holding” and “Middle Age Crazy” — two songs on the same topic of getting old by Jerry Lee Lewis

    “Highway 20 Ride” — Zac Brown, about a divorced dad traveling to pick up his son for a weekend visit.

    “Don’t Cry Daddy” — Elvis Presley, about a daughter comforting her father after their mother leaves him.

    “Sunday Morning Coming Down” — Johnny Cash, an alcoholic walks out to greet Sunday morning…

    “Cafe Down on the Corner” Sawyer Brown, where all the farmers who’ve lost their land meet for coffee and breakfast…

    “Sitting on the Dock of the Bay” — Merle Haggard/Willie Nelson, but same treatment as Otis Redding.

    “I Just Came Home to Count the Memories” — John Anderson, to me, sadder than “Who’s That Man”… “That Johnson boy from down the road was asking if the kids could come and play./Lord I wish I could have told him yes but I just said, ‘I guess son, but not today.'”

    “All the Gold in California” — Larry Gatlin “is in a bank in the middle of Beverly Hills in somebody else’s name…”

    “The Beast in Me” — Johnny Cash, such a dark song

    “High and Dry” — Marty Brown

  21. Hello says

    This list was great, but I would have loved to see Three Wooden Crosses by Randy Travis and Whiskey Lullaby by Brad Paisley up there too.

  22. jacob says

    What about Conway twitty’s “that’s my job”? That one deserves a spot on the list

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