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10 Saddest Kenny Chesney Songs That Will Make You Cry

Kenny Chesney is a big name in country music. With hit songs like “No Shirt, No Shoes, No Problems” under his belt, the country singer is a favorite for many fans. 

But, every so often, the singer releases a sad song, and fans love it! This list has been selected for their emotional themes and sound and is the ultimate sad songs list for your breakup playlist. 

So without further ado, here is my list of the saddest Kenny Chesney songs of all time.

1. Somewhere With You

First up on my list of the saddest Kenny Chesney songs is “Somewhere With You.” Released in 2010, the song features on Chesney’s album Hemingway’s Whiskey and is a love ballad that tells the story of a breakup. 

“Somewhere With You” will tug at your heartstrings as the song describes missing that special someone that is no longer in your life. Give it a listen today and feel the longing creeping back into your heart. 

2. Never Wanted Nothing More

“Never Wanted Nothing More” was released in 2007 on the album Just Who I Am: Poets and Pirates, and was also nominated for a People’s Choice Award for Favorite Country Song that same year. A song about living life with no regrets, the song is one of many that deal with the challenges we all face in life. 

Give “Never Wanted Nothing More” a listen when you add it to your sad Kenny Chesney song list, and let your mind wander about the path you are on in life. 

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3. Come Over 

It’s hard to believe that the song “Come Over” is already a decade old! Released in 2012, the song featured on the album Welcome to the Fishbowl. It is a rather different love song that tells the story of two people who know they are not good for each other but somehow still find themselves intertwined in each other’s lives. 

“Come Over” will have you thinking of that one person that you will never really let go of and features at number three on my list. Grab the tissues and add this song to your playlist today. 

4. Out Last Night

We all try to hold onto the happy memories of our youth as we grow older. “Out Last Night” is a song by country singer Kenny Chesney that will have you feeling nostalgic as you, too, think back on the parties you used to go to when you were younger. 

Released in 2009 on the singer’s Greatest Hits II album, “Out Last Night” has a more upbeat tune but makes it onto my list as one of those songs that will make you miss your friends and those who are no longer with us. Give it a listen today, and remember to add it to your playlist, too. 

5. You and Tequila (Feat. Grace Potter)

Kenny teams up with Grace Potter in this heartbreaking duet that was released in 2010 on the album Hemingway’s Whiskey. Breakups are hard, and as the lyrics in “You and Tequila” tell, trying to get over that one person can be hell. 

Whether you take comfort in drinking your pain away or turn to good old chocolates and candy, we all find that one vice that is used to replace what you have lost. “You and Tequila” takes up the number five spot on my list. Add it to yours today, and let Kenny Chesney ease your pain. 

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6. When I See This Bar

Kenny Chesney sings of the memories of adolescence in 2013’s hit song “When I See This Bar.” The song was featured on Kenny’s album Life on a Rock and is based on the real-life memories of his days at college. 

We all have that one group of friends that will always be in each other’s lives, and for many, the song will trigger those happy and not-so-happy moments we had growing up. Travel back in time to your youth when you add “When I See The Bar” to your playlist. 

7. Don’t Blink

I always thought people were overexaggerating when they said that the years go by in the blink of an eye – Until I experienced it myself. Kenny Chesney reminds us to hold onto what is special to us in his hit song “Don’t Blink.”

With just over 64 million views on YouTube, it is clear that this 2007 release is a fan favorite. Featured on the album Just Who I Am: Poets and Pirates, the song is sure to have you feeling nostalgic as you look back on your own past and realize that, yes, life does indeed pass by very quickly. 

8. The Boys of Fall

If you’ve ever been on some type of sporting team, you will know that it is so much more than just a sport, and your teammates become like your brothers. Kenny Chesney shares his sorrow as he recalls the happy memories of playing football as a youngster. 

Released in 2010 on the album Hemingway’s Whiskey, the song has a home-town country feel to it as it tells of a childhood playing sports and having fun. With its melancholic tone, “The Boys of Fall” makes a great addition to your Kenny Chesney song list. Add it to yours today!

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9. The Good Stuff

If you need a song to remind you about the good things in life, Kenny Chesney’s 2003 hit song “The Good Stuff” is it! Featured on the album No Shoes, No Shirt, No Problem, the song will have you counting your blessings in life twice, so be sure to give it a listen. 

“The Good Stuff” is a personal favorite of mine and is a must-listen if you love those feel-good songs that help you remember how lucky you are to be alive. It features at the number nine spot on my list. 

10. Setting the World on Fire (Feat. P!nk)

The song “Setting the World on Fire” was released in 2016 on Kenny Chesney’s album Cosmic Hallelujah. Featuring the vocal talents of superstar P!nk, the song has an upbeat tune as it tells the story of a powerful kind of love that has you feeling euphoric. 

“Setting the World on Fire” will hit you in your feels as you wish for the kind of love that Chesney and P!nk sing about, and it is a must for your playlist of the saddest Kenny Chesney songs.

Jodi chesney

Friday 21st of July 2023

Me and you how

Jodi chesney

Friday 21st of July 2023

Whatever it takes me and you