The Saddest Country Songs of All Time

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

Garth BrooksThe 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

Toby KeithIn 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

Lee Ann WomackIn 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

Alan JacksonIn 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.

Entire List

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

The Saddest Country Songs of All Time Part 5

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. says

    i love all country songs more when im sad i like to put on my radio a hear music cuz when im sad thats wheat makes me happy hahah i love rascasl flatts i love the song what hurts the most cuz it makes me remember the good times with my sister now thats she is died i only have pics of us and the good times we had together


  2. says

    I like lots of country songs. the 2 greatest country sad songs are ‘What Hurts the Most’- Rascal Flatts & ‘There Goes My Life’- Kenny Chesney