Country music is well-known for having sad songs.
Country music artists pour their emotions into their songs. The truly great songs are passionate, emotion, and have great melody so fans can sing along.
Sad country songs connect with fans because the songs let listeners know they’re not alone with their feelings of heartache, disappointment, loneliness, grief, and depression. Country music an be therapy for listeners and it’s a reason why so many love country music.
Let’s take a look at the saddest country songs of all time…
Sad Country Songs
50) A Picture of Me (Without You) – George Jones
Mr. Country Music – George Jones had the voice of the 2nd most soulful white guy according to Frank Sinatra. Nobody could sing an emotional sad country song like George Jones. In 1972, Jones released the song A Picture of Me (Without You) was released and it went on to become a top five hit. The song remains one of George’s signature songs. The song sees the narrator telling his lost loved one that if she only imagined life without all of the important things she might just understand what his life is like without her. It’s a sad song, but a common feeling for those that are without a loved one and that’s why it’s one of the saddest country songs of all time.
49) I Wonder Do You Think Of Me – Keith Whitley
Shortly after his death I Wonder Do You Think Of Me became Keith Whitley’s first #1 posthumous hit. The song is about a guy that is still in love with an old flame. He often wonders if she thinks of him like he thinks of her. The song took on extra meaning for Keith’s fans as they continued to love him and his music even after his passing. Keith Whitley made his career by singing melancholy songs that allowed him to share his own personal heartache, sorrow, and depression with the world. Fans connected with the honky tonk-bred singer and he became a star. Whitley passed in 1989 after spending time drinking alone. Keith’s apparent loneliness showed in his songs. His willingness to share his feelings with fans is what made him so endearing. Keith Whitley remains one of country’s most remembered figures and it’s too bad he couldn’t stick around a little longer.
48) It’s Your Song – Garth Brooks
The only single from his Double Live album in 1998 was It’s Your Song. Garth Brooks took a song written by some of Nashville’s finest songwriters and used it as an ode to his Mom. Brooks’ mom was suffering with cancer at the time and the song was a dedication to the impact she had on him and his career. Behind all great people there are usually others that have had influence and inspiration. When Brooks would sing It’s Your Song everyone in the audience shared in the emotion and passion he put behind every lyrics. The song was one of Garth’s most emotional songs and it reached the top ten on the charts. The song is sad for those that have lost someone special in their lives that has had influence and positive impact. For those lucky enough to still have that person in their lives It’s Your Song is perfect for expressing your feelings of appreciation.
47) Who’s That Man – Toby Keith
In 1994, Toby Keith kicked off his sophomore album Boomtown with the #1 single Who’s That Man. The song is about a guy driving around his old house. He sees his yard, his driveway, and finally his wife and kids. Then he wonders who the new man is. It’s the classic song about a divorce situation where one side of the relationship is moving on with their lives while the other is still struggling to live life in a new way. Toby plays the guy that is left wondering what he screwed up and how another guy could be taking his place. The song connected with listeners all over that were going through the same situations. It’s gotta be difficult for men and women to divorce and try to move on with their lives. There seems to always be sadness involved and that’s why Who’s That Man is on this list.
46) The Fool – Lee Ann Womack
In 1997, Lee Ann Womack released her sophomore single and the song reached the #2 spot on the charts. The Fool is a song about a woman that keeps falling for a guy that doesn’t appreciate her. He is still in love with another woman and the narrator realizes she’s a fool for falling for someone she knows will never love her back the way she deserves. Lee Ann puts her signature country vocals on the track. The Fool oozes heartache and emotion and that’s why so many connected with the song at the time of its release. Even today the song remains a favorite for women that are feeling a little sad and discouraged with the way their relationships are going. Country music is about healing and understanding. Sad songs like The Fool let people know there are others out there going through similar situations.
45) Your Cheatin’ Heart – Hank Williams
Released shortly after his death, Your Cheatin’ Heart is known as one of Hank Williams signature songs as well as one of the greatest country music songs of all time. The song sees the narrator telling his cheating lover that he cheating ways will eventually catch up with her. The recognizable vocal treatment of Hank Williams is known instantly when the song comes on. The heartache and passion that come through the recording is enough to make every listener sit back and take notice. The song is sad for those that have been scorned by loved ones in the past. Cheating is an all too common occurrence for many and that makes it one of country music’s most sung about topics. Your Cheatin’ Heart is one of the original cheating songs and remains a favorite still today.
44) The Little Girl – John Michael Montgomery
In 2000, John Michael Montgomery had a somewhat surprising #1 hit with the heartfelt song The Little Girl. The sad song is about a girl that is neglected by her parents. Her Dad drinks and her Mom does drugs. The girl was never taken to any kind of church as a child yet one night the little girl was found hiding behind the couch after her dad shot her mom and killed himself. The girl is taken to Sunday school for her new life and she recognizes a picture up on the wall. She isn’t sure exactly who it is but she says he was there the night that her parents died. It’s a tear-inducing song that connected with millions across the US. The song takes on a rough subject, but one that is all too familiar for so many in the world. The song served a reminder that positive influence from individuals can have an impact on people.
43) A House With No Curtains – Alan Jackson
In 1998, Alan Jackson was going through some difficult times with his wife. They were struggling with their own issues and there was even some drifting away from loyalty at the time. Alan’s wife Denise admitted that the problems were a result of a both people. Alan released the song A House With No Curtains in 1998 and even though it only reached #18 on the charts it became an important song for his career. The song is about a couple that feels like they’re living their broken marriage in front of the entire world just like living in a house with no curtains. The song was co-written by Jackson and it saw him sharing emotions that he must have been feeling at the time. The song is truly sad. It’s not enjoyable when there is difficulty in a relationship. Anyone going through this type of situation knows and this song brings up sad emotions, but it can be therapeutic knowing that others go through the same emotions. Denise and Alan have since repaired their marriage and seem as happy as ever.
42) I Will Always Love You – Dolly Parton
It’s probably her most well-known song and that’s saying something for a career filled with signature songs. Dolly Parton’s own version of I Will Always Love You became a #1 hit for her and an international smash hit for pop diva Whitney Houston as well. Dolly’s version is full of passion and emotion. She wrote the song about her breakup with mentor and business partner Porter Wagoner. Dolly knew she had to go out on her own to achieve the kind of success she knew she wanted. The separation brought about strong emotions and the result was a song that connected with millions. It’s a love song that makes people remember the feelings they have for loved ones in their lives.
41) You Don’t Even Know Who I Am – Patty Loveless
Patty Loveless added the perfect heartfelt, passionate vocal to her 1995 Top 5 song You Don’t Even Know Who I Am. The song is about a woman leaving a man and that man realizing that maybe he doesn’t actually care if she leaves. It’s a sad song about a relationship that went on for a while without either person realizing right away that they weren’t meant for each other. Relationships are a big part of country music. A good portion of relationships don’t work out and there are usually strong emotions in the air when things go bad. You Don’t Even Know Who I Am is a great song for a couple that realizes it’s not meant to be. It can be a sad feeling, but it helps knowing that it happens to others.
40) You Were Mine – Dixie Chicks
The Dixie Chicks were an unstoppable force in country music during their first few albums. The fourth single from their major label debut Wide Open Spaces was the single You Were Mine. The song went on to become the group’s third #1 in a row on the country charts. Sisters in the band Emily and Martie wrote the song together. The sisters wrote the song about their parents divorce. It’s a heartfelt ballad about a love that’s lost. It’s a song that brings about sad feelings and emotions. The vocal was added by lead singer Natalie Maines and her unique vocals made the song something special. Sometimes love just doesn’t work out and it can be tough to move on for both people. When one side moves on it’s even more difficult for the other to move on it seems. It’s a common emotion and one of the reasons the song became so important.
39) Don’t Take The Girl – Tim McGraw
It became Tim McGraw’s first #1 country hit. Don’t Take The Girl is a song about a guy deeply in love with a girl. Throughout their lives the guy begs and pleads through different situations to not have his girl taken away from him. A love that deep will always cause some tears and this song remains one of the most played hits on radio today because so many connected with it over the years since its initial release. The song is easy to sing along with and Tim McGraw put a great vocal track to the tune. Don’t Take The Girl is a love song that brings tears to your eyes and while sad there is also a little bit of happiness as those of us that have someone special can think about just how much we love them.
38) Letters From Home – John Michael Montgomery
In 2004, John Michael Montgomery had a bit of a career resurgence with the #2 song Letters From Home. The song is about a solider that is off far away and receives letters from his loved ones at home. The song was an almost an easy hit back in ’04 as US soldiers invaded Iraq, which is nearly 6,000 miles away from the US. Many were missing their soldier sons and daughters that had been coaxed into playing war games for US politicians. Letters took on meaning for soldiers during its release, but getting letters from home can be something special for anyone that lives far away from loved ones. Distance can separate people, but love knows no boundaries. The power of a letter is great and sending a letter to a loved one can still make that person cry tears of joy when they hear from you.
37) The Dance – Garth Brooks
A song with simple lyrics and a simple message took the country music world by storm in 1990. The Dance was released that year and became the 2nd #1 song for Garth Brooks. The Dance would take Garth’s career to new heights and everybody knows that he rode the success to heights unseen before and possibly since. The Dance is a song about someone accepting the chancing nature of life. Knowing that life is going to throw you some tough times is something each of us can remember as we live each day like its special while making the most of every situation. The song is about nothing in particular yet it became the anthem for so many situations about life and being happy. The emotion of the song turns toward sad yet empowering tears when a listener realizes they could live their life better. It’s a powerful realization and a big reason the song became a huge hit.
36) Better As A Memory – Kenny Chesney
Released in 2008 Better As A Memory became a huge hit for Kenny Chesney as it reached the #1 spot on the country charts. The song is a melancholy take on a guy realizing he’s not good enough for the woman he’s with. He comes to terms with the fact that he’s better as just a memory than as her man. The song also contained the title lyrics of the album Just Who I Am. It takes a big person to come to terms with the fact that they just don’t fit the situation and to step away before getting too involved. Sure it could be seen as taking the easy way out with the it’s me, not you line, but Chesney made the sentiment real and genuine. Any breakup is sad and there are usually some sad moments. But sometimes it works out best for both people involved.
35) Anymore – Travis Tritt
The tough guy attitude and the guy who said he’d never get married again defied himself by releasing some of the most emotional and successful ballads of the early ’90s in country music. Travis Tritt released one such song in 1991 with Anymore. The song was from his sophomore album It’s All About To Change and it became a #1 hit for the singer. The song is about a guy that can’t come to terms with living without his lost love. He needs to tell her that he loves. He can’t go on living the way things are without her anymore. When a guy lays his feelings all out on the line it’s a big deal. It’s something that doesn’t happen everyday and women usually take notice when it does. It’s an emotional song full of heartache and passion and it takes on a feeling that causes many to tear up when they think of how it relates to their own lives.
34) Real Life (I Never Was The Same Again) – Jeff Carson
After five years without a big hit singer Jeff Carson came back to the charts in a big way in 2001 with the song Real Life (I Never Was The Same Again). The song is about a guy that remember three key moments that changed his life. The first is when his childhood dog dies. The second is when he makes it through his blurry, fun college years and the last is when his wife gives birth to their first baby. There are many life changing moments for everybody. Jeff Carson added some heartfelt emotion to the lyrics as he told the story of a guy that remembers a few of his life changing moments. It can be emotional to recognize the times when real life took over. It’s emotional. It’s powerful and it can bring tears of joy when you think about them.
33) She Misses Him – Tim Rushlow
Tim Rushlow was no stranger to success. As the lead singer of the group Little Texas he was with the band during their heyday in the late ’80s and early ’90s. In 2001, however, he reached solo success with the song She Misses Him. The song climbed into the country top ten that year. She Misses Him is about a man that falls ill, mostly interpreted as signs of Alzheimer’s. His loved ones take care of him, visit him and remember the man he was. It’s very sad for those affected by the outcome of a loved one that falls ill and is no longer the person they once were. The song served as a bit of therapy for many even though it was extremely sad. It’s good to hear sad songs when a song can show you you’re not the only one going through a difficult situation.
32) Where Do I Fit In The Picture – Clay Walker
Clay Walker’s debut album was released in 1993 and it became an instant hit. The album yielded four big hits including 3 #1 songs. The only song not to reach the top spot was a song written by Clay himself without help from a co-writer. Where Do I Fit In The Picture is a song about a lonely guy that is coming to the realization that he and his woman are beginning to live lives that are taking them on separate paths. The narrator is finding it difficult to come to terms with the fact that he is no longer in the picture of his woman’s future and it makes for one sad country song. The tune only peaked at #11 on the charts, but remains a great piece of work on the extensive resume of Clay Walker. Clay is still going strong today releasing new music and staying on his heavy touring schedule each year. He doesn’t perform Where Do I Fit In The Picture much anymore, but it remains a favorite of his die hard fans.
31) Cold, Cold Heart – Hank Williams
The biggest legend in country music released Cold, Cold Heart in 1951. The song would go on to reach the top spot on the country charts that year. Today the song remains one of Hank’s most well-known songs as well as being one of the saddest country songs of all time. The song is about a frustrating lover that falls for a woman, but she can’t give herself to him because she’s been scorned by another in the past. She can’t get over the way she was wronged and it’s frustrating to the narrator of the song. Neither is able to overcome her cold, cold heart. It was a unique song at the time and remains unique even today as not many have been able to write songs quite like Hank.
30) What Mattered Most – Ty Herndon
It isn’t often that a kid out of nowhere comes out with a song that hits home with so many country fans. In 1995, such a thing happened with newcomer Ty Herndon. The song was What Mattered Most and it shot straight to the top spot on the country charts in just a few weeks in 1995. The song is about a guy that lost his girl. The guy realized he knew all of the things on the surface, but never paid attention to what his woman actually wanted. He didn’t pay attention to her dreams and what she wanted for her life. As a result he lost her and the love they had. It’s a sad song and Herndon put an amazing vocal on the track and became an overnight sensation. Ty repeated the success a few more times. He was down and out for a few years, but is back touring and recording again. It all started with one sad song back on 1995.
29) I Can’t Do That Anymore – Faith Hill
Faith Hill was on a roll by the time she released the 5th single from her sophomore album. The song was an unlikely hit yet it reached the the top ten at the tail end of ’96. The song was I Can’t Do That Anymore. It was written by fellow country star Alan Jackson. The song tells the story of a woman sick and tired of letting her husband follow his dreams while she stays home and lives her life 100% for him. Woman need a little something of their own as the narrator in the song says. It’s a sad song that is a true story for many out there are supporting their loved ones in a way that takes away everything they have. Relationships seem to be best when each gets to follow their dreams.
28) Believe – Brooks & Dunn
In 2005, the greatest duo in country music history had one of their biggest hits. Even though Believe by Brooks & Dunn only reached #8 on the charts it’s gone on to become one of their fans’ favorites. The song tells the story of a young man that learns from a few stories an old man tells him over the summers. The song is religious and hopeful for life with loved ones after the one we live on Earth. It’s positive and yearning. There has to be more than just one trip around. All the hurt and pain…there has to be more. For B&D the song touched many that yearned for more and the song brings about tears in just about all fans’ eyes when it comes on over the radio speakers. Those are the powerful sad songs – the ones that share emotion that others feel.
27) Teardrops On My Guitar – Taylor Swift
Newcomer Taylor Swift had her second big hit on the American country charts in the middle of 2007 with the sad teenage country song Teardrops On My Guitar. The song was catchy as all hell and every heartbroken teen girl was singing the blues along with Taylor. The song is a story about a girl that falls for a guy that is with someone else. The narrator sees signs that maybe, just maybe he actually likes her a little more, but in the end her crush, Drew, just doesn’t share the same feelings. It’s heartache in the purest form and 16 year old Taylor was able to capture the emotion of a million other young girls were going through and the song catapulted Taylor Swift to superstardom.
26) Monday Morning Church – Alan Jackson
More loved lost hit home with Alan Jackson and his 2004 top five hit Monday Morning Church. The song is a story told by a narrator that has lost his wife to death. He is dealing with a wavering faith. He just can’t understand why the one he loved most in the world was taken from him. He’s left with only himself and the pain and emptiness he has. He says that his heart is now as empty as a Monday morning church. There is no better sad song country singer that Alan Jackson. AJ Was inspired by the soulful singing of George Jones and it shows on emotional tunes like Monday Morning Church.
25) Stupid Boy – Keith Urban
Country pop singer Keith Urban had an unlikely hit in early 2007 with the somber Stupid Boy. The song was co-written by fellow country singer Sarah Buxton. The song is written in the perspective of a woman that was scorned by her stupid boy. Urban knew the song was special and his wife Nicole Kidman convinced him that he could sing it as the stupid boy that screwed up. He took her advice and the song became a top three hit and one of today’s saddest country songs. There are a lot of stupid boys out there that take for granted the love they have from wonderful girls. Even if they realize it later on it’s usually too late for the guys to fix things. They simply need to learn from their own mistakes and hope for the best when love comes back around again.
24) I Miss My Friend – Darryl Worley
For his second album country singer Darryl Worley released the passionate, soulful song I Miss My Friend. The 2002 song raced right up the charts and became Darryl’s first #1 hit. The song is a sad tale of a guy that lost his lover and his best friend in the world. He misses his best friend that was his former lover. The song hit home with lots of folks that were feeling the same kind of loneliness. When it comes to breaking up with a girlfriend or boyfriend, husband or wife there is a lot of questioning that goes on in each others’ minds. Was it right to break up? Can you get back together. It’s enough to drive you crazy. The only thing that can heal the pain is time and to help pass the time there are songs like I Miss My Friend.
23) Can’t Be Really Gone – Tim McGraw
In the mid and late ’90s Tim McGraw had a run like no other. His songs all seemed to skyrocket to the top of the charts. One of those songs was the heartbroken sad ballad Can’t Be Really Gone. The song reached #2 at the tail end of 1995 and became one of his cult fan favorite hits. The song is about a guy that just can’t come to terms with the fact that his lover has left him. He keeps walking through the house and seeing all of her things. How could she just up and leave without taking all of the stuff she cared about so much? She can’t be really gone… It’s the denial part of loved lost and it’s an emotion felt by many that find themselves in breakups. It’s a great sad country song and one that truly belongs on this list.
22) When I Call Your Name – Vince Gill
Vince Gill had a breakout hit in 1990 with the powerful sad song When I Call Your Name. The song is classic country heartbreak. The song is a story about a guy that comes home and hears nothing when he calls the name of his lover. She’s left him after realizing she was living a lie by being with him. Sometimes one person in a relationship realizes that it’s just not going to work out and they have to leave and get on with their life. It’s too bad yet it’s probably for the best. The person that is left is taken aback like the narrator of this song and that leads to heartbreak. It makes for a great country song and one that people can relate to. The song made Vince Gill a star and he’s still going strong today.
21) Miss Emily’s Picture – John Conlee
In 1981, classic country singer John Conlee came out with the #2 hit Miss Emily’s Picture. The song is a sad tune about a guy that has lost a loved one. He struggles to get through each day without her. The poor guy keeps running into all the pictures of his Miss Emily throughout the day and it keeps bringing about the memories he had with her. It’s painful when you lose someone and there is just about no lonelier feeling that knowing you’re no longer going to be with someone you love. The song has a lonely melody and fits right in with someone going through love lost. Even though it’s sad the song serves as one of those songs that can heal through it’s storytelling. By knowing others go through the same thing Miss Emily’s Picture is a classic country therapy song.
20) I’ll Wait For You – Joe Nichols
Joe Nichols had a little career resurgence with his album III. The third single from the album was the heartfelt ballad I’ll Wait For You. The sweet song is about a couple that waits for each other when they get caught up in life’s situations. They always make sure they do the important things together the best they can. I’ll Wait For You is a happy song that makes people tear up with the sentimental ending of the song where the man finds out his wife has died. His loved one left him a note making sure that he knew she’d wait for him. Even the love songs can be sad sometimes.
19) Alyssa Lies – Jason Michael Carroll
It’s difficult to break out as a new country artist, but newcomer Jason Michael Carroll did just that in 2006 with his debut single Alyssa Lies. The song’s topic generated a lot of buzz around the country music world and fans called in to request the song about the sad little girl. The girl in the story was Alyssa and she was the best friend of the narrator’s daughter. Alyssa would come to school each day with bruises and lie about where she got them. At the end of the story the narrator finds out that Alyssa has died. The narrator tells his daughter and the two cry together. There is a lot of evil in the world including child abuse. It’s a touchy subject but when the situations make it to the mainstream it helps to bring awareness. People will help other people in need. It’s how we all react. We want to help those in need. Alyssa Lies is a great but sad song. It’s definitely worthy of a spot on this list.
18) There Goes My Life – Kenny Chesney
It’s a fan favorite song in a collection of songs that includes no less than 30 huge hits. Kenny Chesney released the song There Goes My Life in 2003 to kick off his When The Sun Goes Down album. The song became a smash hit and reached the top spot on the country singles charts this year. There Goes My Life is about a young couple that finds out they’re having a baby while still in high school. The story is told from the perspective of the young dad. He works hard and along with his amazing wife he is able to raise a wonderful little girl. The same girl that started out as a scare and a surprised turned out to be his entire life. He realizes it when she packs up her car and heads off to college. It’s a sad moment for many parents when their kids drive off to live on their own. And that’s why this great song made the list.
17) Best I Ever Had – Gary Allan
Country star Gary Allan was going through some tough times by the time 2005 rolled around. He was going through the death of his wife and was dealing with the reality of raising six kids while remaining a touring country singer. Allan recorded the somber Vertical Horizon song Best I Ever Had. The song was a sorrowful tune that saw Gary pouring his heart out into every note. The tune turned out to be a great country song and it reached the country top ten. Gary Allan brings a unique raspy country voice and has found a unique place in country music as a bit of a rock guy. He brings his emotion to his music and shares his feelings with his fans. Best I Ever Had allowed Gary to do some healing and I’m sure a few of his fans were able to heal right along with him.
16) It Matters To Me – Faith Hill
After a hugely successful debut album Faith Hill followed up in 1995 with yet another album full of hits. The second single from her sophomore album was the title track It Matters To Me. The song is the cry for help of a woman that needs more from her man. She tells him that she isn’t sure if he even cares that they don’t talk, don’t touch. It matters to her, however, and he’s going to need to learn that or else she’s hitting the road. The song became another #1 hit for Faith at the end of ’95 and she went on to have many more top hits in her career. Many of Faith’s fans still remember the sad song that helped make her a star. It Matters To Me remains relevant today as many women still yearn for a little more from their men.
15) Someone Else’s Star – Bryan White
In 1994 a 20-year old singer that sounded a little like Steve Wariner came onto the scene with a few minor country hits. It wasn’t until ’95’s #1 hit Someone Else’s Star that singer Bryan White finally broke out as a legit country star. The song that made Bryan famous was a heartbreaking ballad. Someone Else’s Star is a tune about a guy that feels like he just can’t find someone to love. He keeps wishing on all the stars up in the sky but things never seem to work out. Finally the guy realizes that he must just be wishing on someone else’s star. Everyone seems to be falling in love but him. It’s a lonely feeling when you don’t have someone to love. It’s good to know that others out there feel the same way. And perhaps you’ll run into one of the lucky ladies or guys out there that is looking for someone just like you.
14) Feed Jake – Pirates of the Mississippi
Pirates of the Mississippi had their biggest hit with 1991’s Feed Jake. The song reached the #15 spot on the country singles charts and remains a popular tune on classic country stations today. The song is about a guy that knows he’s going to die at some point. He prays to have someone take care of his good dog Jake. Death is sad to think about most times. People generally are afraid to think about what things will be like when they’re gone. Those that are most accepting of the fact seem to think about what really matters in their lives. Sometimes that can be the love of a best friend and dog. The video for Feed Jake also brought up some issues of tolerance and acceptance. The song is sad and powerful and remains one of the greatest country songs of all time.
13) Hurt – Johnny Cash
In 2003, Johnny Cash released what would be one of his final singles. The song was a cover of a Nine Inch Nails song. Hurt took on a bigger meaning for Cash’s recording and the video was powerful and had a huge impact on country music during the end of Johnny’s life. The song took on a new life and meaning for Cash as he looked at his life and upcoming death. Cash died just a few months after its release. The video went on to win awards and acclaim and is recognized as Johnny’s epitaph. The song’s writer Trent Reznor even said he was amazed by Johnny’s version. The song struck a hard line with so many fans as they realized they were losing a friend that had been with them, entertaining them for so long. It was the final send off to one of the greatest country singers of all time.
12) The Car – Jeff Carson
There is something about a car that makes a young guy tick. Freedom, speed, and taking on a new responsibility are all feelings a young kid feels the first time they get behind the wheel of their first car. In 1995, Jeff Carson had a hit with the song The Car. The tune is the story of a single father raising his son. The song covets an old Mustang, but he realizes that his dad just can’t afford it. The dad works hard and both dad and son grieve the loss of their wife and mother. The son yearns for the car, but what he really wants is just a little time with his dad. Finally the story turns to the death of the father. The son says his final goodbye and realizes that his father had given him the keys to the Mustang he had so long wanted. The dad apologizes for not being able to be there to fix it up and spend time with his son. The song is enough to bring tears to the eyes of any guy that can break down and listen to the song. It’s touching, sad, and one of the best country songs of all time.
11) D-I-V-O-R-C-E – Tammy Wynette
In 1968, country diva Tammy Wynette released one of her signature songs. D-I-V-O-R-C-E is a classic sad country song about a couple that is deciding to call it quits. They know they are no longer happy together and they aren’t quite sure how to break it to their little kid. Little Joe doesn’t understand that his parents are separating. The parents spell out their words and watch their tones so they don’t make the little boy sadder than he’ll be when he’s old enough to realize. Divorce is an extremely difficult thing for kids, but if the parents aren’t happy it has to be the better option for all involved. It just takes kids a little longer to realize.
10) Concrete Angel – Martina McBride
Martina 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
By 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
In 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
In 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.
More Sad Country Songs…
There was no more holding out. I had to add to the list of Sad Country Songs. It’s been the most popular series in the history of CML and with all of the suggestions for more sad country songs I thought I’d put together another post with more songs.
These include every song you’ve mentioned in the comments along with a few others I thought fit the sad situational country songs.
It’s not that we want to be sad all the time, but when we’re feeling a little down these are the songs that help us know we’re not alone in the world. Country music has always had a way with sadness and these are more of the songs that make it the best genre of music.
So with a little tip of the hat to George Strait and his 22 More Hits album we continue with…
17 More Sad Country Songs
1. Whiskey Lullaby – Brad Paisley & Alison Krauss
This was the most requested addition to this list. In 2004, Brad Paisley and Alison Krauss had an unlikely it with Whiskey Lullaby. The song about a double suicide kind of surprised a lot of people since the subject isn’t really made for a safe country song. Brad and Alison really made this a great track as they took the story and added the emotion necessary to tell it. It’s a huge song and one that definitely belongs on the list of the saddest country songs of all time.
2. Chiseled In Stone – Vern Gosdin
Some of us get lucky in life. Some of us get the chance to learn from the life lessons of others. With his well known song Chiseled In Stone Vern Gosdin played the role of a guy that gets a second chance. The narrator has an argument with his woman. He heads to the bar where he finds an old timer. The guy he meets tells him he ought to feel lucky. He has someone to go home to. He tells him he’ll never know lonely till it’s chiseled in stone on her grave. Now that’s a warning and it’s too bad it came for the old man in the bar.
3. Probably Wouldn’t Be This Way – Leann Rimes
There are a lot of opinions about Leann Rimes these days, but all I care about is the fact that she can sing the hell out of a country song. As Leann came into her own as an adult singer she really found a great song with Probably Wouldn’t Be This Way. It’s the story of a woman trying to move on from the loss of her lover. She’s looking at going out on dates, but she can’t take herself away from the one she’s lost. She sees him at his grave and just has the hardest time moving on. It’s sad, but that’s how life is sometimes. It’s a great track.
4. I Sang Dixie (As He Died) – Dwight Yoakam
It’s hard to believe I left Dwight off the list the first time around. He’s classic country and a few of hits should qualify as pretty sad country songs. With I Sang Dixie Dwight sings about the loss of his good friend. He just sings Dixie as his buddy passes on. It has to be sad to see someone you love slip away to the next life. It’s something that happens to all of us at some point in life and with songs like this we know we’re not alone.
5. Today My World Slipped Away – George Strait
Divorce is getting common these days. It’s hard to know if people are really falling out of love or if they’re simply getting married too soon. Whatever the reason there is no doubt divorce is common. George Strait sang about divorce with his song Today My World Slipped Away. It’s the story of a couple at the courthouse making things final. The woman is ready to move on, but the guy isn’t really ready. He feels like his entire world is getting away from him. He’ll probably be alright, but right now he feels like he has nothing. Now that’s a sad song.
6. Baby’s Gotten Good At Goodbye – George Strait
This is the second George Strait song on this additional part of the list. George can really sing about anything and make it have an impact on the listening audience. Back in 1989 he took the somber route and really had himself a big hit with Baby’s Gotten Good At Goodbye. It’s the classic song about a guy not being up to a woman’s standards. She leaves and he’s left alone. I guess it’s become a classic sad country song, but George always seemed to be an original.
7. Almost Home – Craig Morgan
Back in 2002 there weren’t a lot of people that knew about Craig Morgan. He knew he had the potential and it just took that one breakthrough hit to really get the attention of the general country audience. The song was Almost Home and it really became a surprise hit during its run on the charts. It’s about a homeless man that kind of inspires the narrator of the song in a way. Things begin pretty sad in this story and eventually work out to the understanding that life is too good to throw away.
8. Sissy’s Song – Alan Jackson
Alan Jackson released this song back in 2009. It was his tribute to his late housekeeper. Alan has released plenty of somber tunes in his 20+ years of hit making, but this one had a different sound to it. Alan really poured emotion into this track and it’s obviously because he felt strongly for his lost friend. We all suffer difficult losses in life and even if we hear a song about someone else we can always put our own stories into the context.
9. Dear Me – Lorrie Morgan
Lorrie Morgan can still sing a country song. She’s one person I’d love to see in concert and I hope I get the chance someday soon. With songs like Dear Me Lorrie really showed just how special her voice is. She could sing the hell out of a sad country song. Dear Me is about a woman that’s lost her man. She screwed things up and now he’s gone and probably for good. She’s only realizing now that he’s gone just how good they were together. All the plans are out the door and life is going to be different. That’s a sad feeling.
10. If You Came Back From Heaven – Lorrie Morgan
With this track Lorrie sings about love and loss. The track is about the love of her life leaving her. There is a ton of sadness in the story and plenty of emotion in Lorrie’s vocals. She’s one of the best singers of all time and hearing her sing about maybe having the one chance to see her loved one again is enough to bring tears to your eyes.
11. The Last One To Know – Reba McEntire
Often in relationships there is one person ready to move on while the other is obliviously to the waning of love. It’s not really being oblivious as much as it is about just not seeing what is right in front of you. That was the case for the narrator in Reba’s song The Last One To Know. She didn’t see things coming. She didn’t realize she was in a dying relationship. There is no one better than Reba. She can sing any kind of song and that includes a classic sad country song.
12. Don’t Close Your Eyes – Keith Whitley
If you want sad country songs you need to listen to the classic hits of Keith Whitley. The man seemed to have sad life if you just listen to his collection of songs. One of the tracks that really hit home with country fans was Don’t Close Your Eyes. This song really cemented Keith’s status as a rising country superstar. It’s about a man that knows his woman doesn’t really love him. All he wants is for her to think of him and keep her eyes open when they’re intimate. It’s a sad situation and one most of us hope to never be in.
13. All The Good Ones Are Gone – Pam Tillis
There is something about being 30 years old that drives women nuts. I can’t say what it is since I’m a guy, but when women turn 30, especially if they aren’t married and don’t have kids, they go a little crazy. There must ben some kind of clock in their head that makes them think about if they’ll ever find love and be able to have a family. I suppose it’s a little sad depending on the situation and it’s just the sentiment Pam Tillis sang about with her big hit All The Good Ones Are Gone. This song still makes me feel a little sad and I’m not even a woman. It’s just a great track from one of my all time favorite artists.
14. Cryin’ For Me (Wayman’s Song) – Toby Keith
In late 2009 Toby Keith kind of caught everybody off guard with his sad country song Cryin’ For Me (Wayman’s Song). The song was Toby’s tribute to the late basketball superstar and jazz musician Wayman Tisdale. The two had formed a relationship around their love for music and when Toby got the news about Wayman’s death he sat down and did what he does best – write a great country song. For fans the song had to catch them off guard a bit. Toby is usually all about bravado and masculinity, but we see the softer side of him on this emotional song.
15. 21 to 17 – Doug Supernaw
When we think back on the impact artists of the 1990s we don’t often include Doug Supernaw. And it’s not our fault. Doug had something special going after a run of successful albums and albums, but he threw it all away when he couldn’t keep control of his life. That’s how things work out sometimes. In late 1999 we got our last bit of country music from Doug. He released the track 21 to 17 and even though it didn’t chart the video for the song saw some play on the country channels. It’s a song about a young couple that finds themselves breaking up just as the local high school football team wins their homecoming game.
16. When She Cries – Restless Heart
By 1992, Restless Heart had lost their main lead singer and were probably wondering if they couldn’t continue their run at the top of the country charts. All worry subsided when the band released what is often considered their biggest hit – When She Cries. The song shot into the country top ten and became a crossover hit on multiple charts including pop and adult contemporary. The song is about a man that realizes he’s making his woman sad to be with him. She’s crying and he’s sad about making her cry.
17. Lucille – Kenny Rogers
Kenny Rogers was nearly 40 years old when he had his first solo number one hit in 1977. The song was Lucille and country fans couldn’t resist the catchy chorus and the sad nature of the song. It’s a story told by a guy that meets a woman in a bar one night. He introduces himself to a woman sitting just down the bar. The woman’s husband comes along and the guy thinks he’s a dead man. Then out of nowhere the husband gets really sad and tells Lucille about how she’s left him at just about the worst possible time. There are a lot of emotions in this song and if you’ve ever been in the husband’s shoes you know it’s sad.