The Saddest Country Songs of All Time – Part 4

Here are the next ten sad country songs…

Sad Country Songs Part 4

20) I’ll Wait For You – Joe Nichols

Joe NicholsJoe 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

Kenny ChesneyIt’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 they’re 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

Gary AllanCountry 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

Faith HillAfter 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

Bryan WhiteIn 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.

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 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. Mike says

    Maybe it doesn’t quite fit in the category of sad songs, but what about the song 20 Years Ago, by Montgomery Gentry?

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