The Saddest Country Songs of All Time – Part 3

On to the next ten sad country songs…

Sad Country Songs Part 3

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 HillFaith 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

Brooks & DunnIn 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 its 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

Taylor SwiftNewcomer 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

Alan JacksonMore 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

Keith UrbanCountry 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

Tim McGrawIn 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.

Update: As one comment points out – the song could also be about losing someone to death. Also very sad.

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.

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 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. Kit says

    The song by Tim McGraw, Can’t Be Really Gone, is actually a song of death. The video shows Tim visiting a grave at the very end.

  2. tj says

    i do not know the name of the song i think it says “drink her memory away” please help me out if you know the tittle i really miss that song!

  3. Joe says

    if you’re going to pick a keith urban song, it’s gotta be “tonight i wanna cry”.

  4. countryman says

    So you have taylor swift on an “all time” list, but no Hank williams jr? Or Merle haggard?

    go listen to some country and try again.

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