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The 35 Saddest Country Songs When You Need a Good Cry

Saddest Country Songs featuring george jones, brad paisley and others

If you need to wallow in heartache, here’s our heavy dose of the saddest country music of all time. 

No matter where we are in life, we’ve all lost someone or something at some point – it could be a lover to another, a job to the economy, our other half to divorce or death, a child who grows up and away, or even our innocence and youth. In this mix of classic tearjerkers and modern country music, you will definitely find something for yourself.

So grab some tissues and take a look at our list of the 35 saddest country songs ever written.

35. “I’m So Lonesome I Could Cry” by Hank Williams

This song has the most haunting lyrics in the country music you could cry. Even The King of Rock and Roll, Elvis Presley thought it’s “probably the saddest song I’ve ever heard.” Everything the singer encounters, from the moon hiding its face behind the clouds to cry to the fact that he’s lost the will to live, Hank Williams perfectly described his dark mood. 

Wiliams initially wrote this song as a poem for his alter ego “Luke the Drifter” to recite, luckily he reconsidered and put melodies into it.

34. “Sunday Morning Coming Down” by Johnny Cash

From the beer he had for breakfast to finding his cleanest dirty shirt and finally, stumbling down the stairs, isn’t it just the worst way to meet a Sunday morning? 

“Sunday Morning Coming Down” is penned by Kris Kristofferson during the lowest point of his life while pursuing to be the legendary songwriter he is now. He was broke, disowned by his parents, and worse, his wife left him and brought their daughter with her. “Sunday was the worst day of the week if you didn’t have a family,” Kristofferson said.

33. “She Thinks His Name Was John” by Reba McEntire

This piano ballad details a dying woman’s dark recollections of a one-night stand she had with a man she can’t put her finger on, but “she thinks his name was John.” The chance meeting with this blue-eyed man resulted in her contracting AIDS. 

She laments how “she let a stranger kill her hopes and her dreams.” She would never know love, marry, or have children. The heart-breaking downbeat storyline was actually inspired by Sandy Knox’s brother, who had succumbed to AIDS. Sandy Knox co-wrote “She Thinks His Name Was John” with Steve Rosen.

32. “Where Were You (When the World Stopped Turning)” by Alan Jackson

Of all the country songs written for the September 11, 2001, terrorist attacks, none stands out more than Alan Jackson’s “Where Were You (When the World Stopped Turning).” It’s a simple song yet powerful enough to expresses what Americans felt that day.

Jackson debuted the poignant song live at the 35th Annual CMA Awards that November, receiving an emotional standing ovation. It went on to earn Jackson a Grammy award, as well as numerous country music honors.

31. “Probably Wouldn’t Be This Way” by LeAnn Rimes

Though most people think that this haunting song is about a break-up, the lyrics “You ought ‘a see the way these people look at me / When they see me ’round here talkin’ to this stone,” suggests otherwise.

The song is, in fact, about the death of a lover, and Lean Rimes confirmed it. “The story is of a woman who is mourning the loss of losing her lover and doesn’t know if she can move on again from that,” the country singer explained.

30. “He Stopped Loving Her Today” by George Jones

There are plenty of sorrowful country songs, but George Jones’ 1980 hit “He Stopped Loving Her Today” stands above almost all of them. The lyrics from Curly Putman and Bobby Braddock narrates about a guy who takes his love for his former flame until he died. She attended his funeral, even though he spent decades pining for her in vain. 

Jones thought the song was too sappy, but he managed to convey it without a hint of sap, and it peaked at the top of country charts.

 29. “D-I-V-O-R-C-E” by Tammy Wynette

The lyrical content of “D-I-V-O-R-C-E” is gut-wrenching enough on its own. Tammy Wynette talked about the internal struggle and pain of so many divorcees-to-be with children very clearly.

Lyrics like “And he thinks C-U-S-T-O-D-Y spells fun or play” and “Oh, I wish that we could stop this D-I-V-O-R-C-E” severely up the misery factor.

28. “Whiskey Lullaby” by Brad Paisley and Alison Krauss

If you’re looking for a fun whiskey song, this isn’t it. The melody is lovely, Brad Paisley and Alison Krauss sung it beautifully, but the lyrics are plain depressing. It details the sorrow of a man drinking away his memories until he kills it.

And its music video is even more miserable. It features actor Ricky Schroder as a World War II soldier who came home after the war only to find his wife cheating on him. Isn’t it dark enough?

27. “Hurt” by Johnny Cash

If you ask someone to name a song that always has the power to reduce them to tears, chances are they’ll quickly reply, “Johnny Cash’s Hurt.” 

The song includes references to heroin addiction and self-harm, although the whole meaning of the song is uncertain. Some listeners claim that the song acts as a suicide note written by the song’s main character, as a result of his depression. Other fans think that it describes the tough process of finding a reason to live despite the pain and depression.

 26. “Jolene” by Dolly Parton

Talk about being jealous of another woman with a beauty that is beyond compare, auburn hair, ivory skin, smile like a breath of spring, the Queen of Country knows better.

With each pleading, “Jolene, Jolene, Jolene, Jolene,” you will feel sorry for how completely helpless Parton was resorting to begging not to steal her lover just because she can and admitting that her happiness depends on Jolene.

25. “I’m Not Gonna Miss You” by Glen Campbell 

“I’m Not Gonna Miss You” is the final song recorded by the legendary country singer Glen Campbell. The ballad’s devastating lyrics detail Campbell’s struggle with Alzheimer’s disease, and the result is a truly poignant experience.

The country song’s music video also made the song even more emotional, which used personal home video and performance clips all through Campbell’s life. “You’re the last person I will love / You’re the last face I will recall / And best of all / I’m not gonna miss you,” Campbell sings as the music video shows the real footage of a doctor showing Campbell X-rays of his brain, detailing how the disease will eat away his memories.

24. “Heaven’s Only Days Down the Road” by Shelby Lynne 

This poignant country song was written twenty-five years after Shelby Lynne’s father shot and killed her mother in the driveway of their Mobile, Alabama home before turning the gun on himself. She and her sister were orphaned and sent to live with relatives.

Over the years, the hurt’s still felt fresh for Lynne. She sang the song from the perspective of her father a few days before his death, as it’s the only way for her to understand her father’s actions.

23. “What Hurts the Most” by Rascal Flatts

This heart-breaking country song is so raw and emotional; it’ll shake you to your core. It tells the story of the narrator losing the love of his life and struggling to learn to cope with it. The difficulty comes with knowing how close they were and having to deal with the fact that he let her walk away.

While many may assume that this is a song about love, in reality, the writer Jeffrey Steele got the inspiration from the passing of his father. And if you want to have a good cry, make sure to check its music video.

22. “Lucille” by Kenny Rogers


Lucille may have picked the fine time to leave her man, but we’re not feeling fine after listening to this. There are a lot of emotions to Kenny Rogers’ first major solo hit. It tells the story of a guy that met a woman in a bar one night. And the woman’s husband, a man whose big heart was breaking, came along.  

Lucille left her husband “with four hungry children and a crop in the field.” The husband had some bad times and lived through the sad times, but this time Lucille’s hurting won’t heal.

21. “Sweet Old World” by Lucinda Williams

You are going to need several boxes of tissues for this one. This country song is written to pay tribute to a loved one who committed suicide. Williams wrote the song in 1979 after a Mississippi-born poet Frank Stanford, with whom she’d briefly been romantically involved, killed himself with three gunshots to the chest.

The song is full of reflection about life, death, and everything that we’ll leave behind. 

20. “If You’re Reading This” by Tim McGraw


Tim McGraw penned this country song with Brad and Brett Warren after he got inspired by a magazine article about war casualties. The lyrics in the song are in the form of a letter a soldier wrote in case he dies in combat. It’s his personal goodbye to his wife and his mother and father.

In May 2007, McGraw brought the mournful ballad to life for the first time at the ACM Awards, and he was joined onstage by military families who lost loved ones while in service to their country. It quickly became one of the most treasured memorial songs in country music.

19. “I Fall to Pieces” by Patsy Cline

Falling in love is thrilling enough, but finding out that the object of your affection no longer feels the same way is pretty devastating. It’s a sad fact of life that your feelings are not always going to be reciprocated, and as painful as it is when it happens, Patsy Cline’s “I Fall to Pieces” knows how you feel.

Raise your hand if you’ve ever been told find someone else to love, this one is for you. The song’s calm honky-tonk beat gives out composure, and Cline does her best to do the same as she keeps herself together in the presence of an old love who wants her to be just his friend.

18. “For My Broken Heart” by Reba McEntire

This country song is so beautiful, so emotional that you’ll find yourself welling up. It’s Reba McEntire, after all. 

“For My Broken Heart” was recorded in the aftermath of the tragic plane crash that killed her tour manager and most of her bandmates on March 16, 1991, after a tour stop in San Diego. For Reba, the victim’s families and friends and the country music community, the tragic loss stopped the world from turning.

17. “Concrete Angel” by Martina McBride

Martina McBride is definitely one of the best country singers of all time. She’s capable of producing songs that pull at the heartstrings at the same time make people aware of difficult topics.

“Concrete Angel,” her final single from her “Greatest Hits” album, is heartfelt and really sad. It was about an abused little girl that can’t get away from her abusers. Sadly, the little girl did not make it any longer and made her way to the afterlife.

16. “Today My World Slipped Away” by George Strait

With chorus, “Cause today my world slipped away/ We buried the plans that we made/And tonight I’m alone and afraid,” George Strait perfectly walks us through the sad life of a man who just got divorced. 

His now-ex-wife is ready to move on, but he isn’t at all. He feels like the whole world is getting away from him. There’s nothing left of his heart, and it’s going to be difficult for him to make a new start. Now that’s a sad song.

15. “Someone Else’s Star” by Bryan White


Bryan White definitely made quite a splash with his 1994 hit “Someone Else’s Star.” In this song, White finds himself all alone and wishing he could find his true love. He blames his lack of good luck and wonders, “Why can’t I be as lucky as those other people are/I guess I must be wishing on someone else’s star.”

14. “Every Other Weekend” by Reba McEntire (feat. Kenny Chesney)

This duet is another heartbreaker about divorce and children. Reba McEntire and Kenny Chesney each sing about the regret they feel every time they drop their children off every other weekend. Both the parents in pain to the fact that their kids are only getting “half the hugs and kisses.” 

“I can’t tell her I love her,” Kenny sings, and Reba echoes, “I can’t tell him I love him” — and the song ends before they can even bring themselves to admit it.

13. “Misery and Gin” by Merle Haggard

It starts with “Memories and drinks don’t mix too well,” and nothing is more spot-on than that. This heart-breaking ballad sings about love lost. The song’s her always ends up at the bar, mixing misery and gin, as he tries to drink away the memories and drown the sorrows. 

However, the spirit of gin does the opposite, and it only makes those moments come back and haunt him.

12. “The Dance” by Garth Brooks

Most fans think “The Dance” is a love gone bad song, but Garth Brooks revealed that the song was more than that.

“But to me, it’s always been a song about life. Or maybe the loss of those people that have given the ultimate sacrifice for a dream that they believed in, like the John F. Kennedy’s or the Martin Luther King’s. John Wayne’s or the Keith Whitley’s,” Garth said. “And if they could come back, I think they would say to us what the lyrics of ‘The Dance’ say.” 

11. “Wish You Were Here” by Mark Wills

Country singer Mark Wills had a huge No. 1 hit in 1999 with his song “Wish You Were Here.” The tearful ballad has captured the hearts of many country music fans as it pulled at the emotions of each listener.

It’s a story of a young, happy couple that has to part ways for a little while only to end up with the guy on a plane crash and a girl receiving the postcard her lover sent her that says “Heaven” on the front. 

10. “This Ain’t Nothin” by Craig Morgan

If you’re struggling to keep things in perspective, take time to listen to this song by Nashville native Craig Morgan. It tells the story of an old man whose old farmhouse outside Birmingham, has been destroyed by a tornado. 

When a reporter asks him how he feels about the loss of his house, the old man replies: “Boy, let me tell you something, this ain’t nothing.” The old man has been through much worse, like losing his dad when he was eight, his baby brother, and his left hand. He even watched his loving wife waste away and die. The story definitely is so deep, and it can make nearly anyone cry. 

9. “Drink a Beer” by Luke Bryan

If you expect drinking beer is all about having fun, you might change your mind the moment you’ll hear Luke Bryan’s “Drink a Beer.” This is actually one of the coolest yet saddest songs you’ll ever hear. The song is actually about someone losing someone close.

The character of the song stunned by a loss of a loved one and choose to honor that person by having a beer, something they usually share. The country star also connects to the song so well because he lost both of his siblings.

8. “Holes in the Floor of Heaven” by Steve Wariner

This three-hankie tune was named Song of the Year by both the Country Music Association and the Academy of Country Music for a reason. 

In it, Steve Wariner’s narrator sings about losing his grandmother the day before his 8th birthday, his wife passed away at a young age and how much he missed her during his daughter’s wedding. Whenever it rains, he is reminded that his loved ones are watching over him, “‘Cause there’s holes in the floor of Heaven/ And her tears are pouring down/That’s how you know she’s watching.”

7. “The Last One To Know” by Reba McEntire 

Often in relationships, there is one person who is ready to move on while the other “the first one to cry and the last to let go.” That was the case for the narrator in Reba McEntire’s song “The Last One To Know.”

She did not see things coming. It was too late for her to realize that she was in a dying relationship. And above all, when it comes to a classic sad country song, no one can do better than McEntire. 

6. “Live Like You Were Dying” by Tim McGraw

 “Live Like You Were Dying” was penned by Craig Wiseman and Tim Nichols. The duo got inspired by the family members of their friend who was diagnosed with lung cancer. They write the song hoping it might inspire someone in such a situation and to send a message to live life to the fullest each day. 

Indeed, it led to many country fans examining their lives.

5. “You Were Mine” by Dixie Chicks

Dixie Chick sisters, Martie Erwin Maguire, and Emily Erwin Robison co-wrote “You Were Mine” in 1995. The poignant song is about their parents’ break-up and subsequent divorce. Their parents know that the song is about them, but they never talk about it. 

“Both our parents are very sweep-it-under-the-carpet. My dad doesn’t want to think it’s about him, because it doesn’t make him look very good, and my mom thinks she’s moved on.” Robison said.

4. “Like We Never Loved at All” by Faith Hill ft. Tim McGraw

The country power couple, Faith Hill and Tim McGraw may have the strongest relationship right now, but the duo knows how to stun everyone with a heart-breaking song. 

“Like We Never Loved at All” is a tale of coping with a love that has drifted away. When the narrator asked, “How can you just walk on by without one tear in your eye?/ Don’t you have the slightest feelings left for me?” – we felt that! 

3. “Just a Dream” by Carrie Underwood

In this Grammy-nominated song, Carrie Underwood sings about an 18-year-old woman going to the church in her wedding dress that you’ll think she’s going to her wedding. However, as the song goes on, it slowly reveals that the woman is actually going to the funeral of her fiancé, who was a soldier who died in combat.

She wishes that everything that’s happening was “just a dream.”

2. “Over You” by Miranda Lambert

“Over You” was written by Miranda Lambert’s then-husband, Blake Shelton, about his experience of losing his older brother in a car accident in 1990, when Shelton was just 14.

Lambert revealed that they both cried while writing the song. Shelton also suggested that Lambert record the song instead of him because he doesn’t think he can get through singing it every night onstage.

1. “I Will Always Love You” by Dolly Parton


Hold back the floodgates when you listen to the original version of “I Will Always Love You.” Although the lyrics sound like she’s about the end a romantic relationship, Parton’s actually ending a professional one.

Parton wrote and sang the song for Porter Wagoner, her mentor, producer, and longtime duet partner. The song represents her desire to make it clear to Porter how much she cared and appreciated him, but it’s time for her to leave the show. 

Heartbreak is definitely at the heart of country music. Maybe because, after all, heartbreak is the common denominator for us all. Luckily, music is here to help us face multiple losses in the midst of tragedy.

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