Celebrate the Heart of Country, Americana, and Roots Music!

Drop Us A Line, Y'all

Y'all interested in advertising, partnering up, contributing stories, joining our team, or just got a question? Well, don't be shy, drop us a line!

Follow Us

15 Top Kenny Chesney Songs Over 25 Years of Country Music

Kenny Chesney Songs
by
  • Arden is a Senior Country Music Journalist for Country Thang Daily, specializing in classic hits and contemporary chart-toppers.
  • Prior to joining Country Thang Daily, Arden wrote for Billboard and People magazine, covering country music legends and emerging artists.
  • Arden holds a Bachelor of Arts in Journalism from the University of Tennessee, with a minor in Music Studies.

It’s almost impossible to rate Kenny Chesney songs from best to least favorite since every single might hit different country lovers differently. However, it would be unfair not to give it a shot. 

The amazing legacy of the country singer, guitarist, musician, songwriter, and record producer reflects in the 20 albums he’s produced with over 40 top singles! 32 of them have reached the No. 1 spot!

RELATED: Let’s Take a Look Back to Kenny Chesney’s Intriguing Dating Life

Here are a few of the timeless Kenny Chesney songs that all have a special place in our hearts.

1. Never Wanted Nothing More

The up-tempo acoustic guitar and banjo combination has done nothing but greatness in country music. Remember the highlights of your life and live it with no regrets.

The song moved up from No. 37 to No. 17 to finally No. 1 on its eighth chart week! 

2. The Good Stuff

There’s no question as to why this song became his fifth No.1 hit back in 2002. The true story of a man who lost his wife and who challenges the whole idea of “the good stuff.”

The song was even written during the time their security guard/friend lost his wife to cancer.

3. When the Sun Goes Down

What does “a song that is going to change the world” sound like? Well, this was how the song was supposed to be written but instead, it talked about an honest struggle of how things might suck sometimes.

Kenny Chesney is no stranger to tough moments, tough times, and tough truths.

A true country working song.

4. Setting the World on Fire

What does euphoria feel like? What does it feel like setting the world on fire while singing in the hallway? This song paints a beautiful blurry scenario where happiness and destruction meet hand in hand.

A topic mostly discussed in his songs, love and pain.

5. How Forever Feels

This song talks about how it feels like to be the right person. Yes, Kenny Chesney can be quite the poet as the song talks about living life to the fullest but still missing one thing, that special someone to spend forever with. 

A certified 90s classic hit.

6. Summertime

Everything’s special in the summer, and this is something the song perfectly talks about. The song is shared by fans as beautiful memories come to life in the classic summertime anthem.

There’s no better time of the year than summertime.

7. Don’t Blink

Kenny Chesney’s greatest hits talk about more than just truck, beer, and whiskey, the country musician likes to tackle life. In this song, the artist talks about how to make the most of your life.

Don’t blink and miss a second of it.

8. There Goes My Life

Reaching No. 1 on the Country charts and staying there for seven whole weeks, “There Goes My Life” tackles a difficult situation where a man suddenly has to face the unplanned pregnancy of his girlfriend. The heavy song is beautifully sung in a comforting way.

It is one of the Kenny Chesney songs that doesn’t beat around the bush.

9. She’s Got It All

One of the love em’ and leave em’ works of Kenny Chesney that just resonates with listeners. The unique neotraditional country sound mixed with the country-pop vibe was one of the more unique creations by the esteemed country artist.

The song was admittedly experimental but in the end, it definitely worked.

10. Out Last Night

The genius of Kenny Chesney is in how he toys with heavy topics spinning them in a light song. The song tackles the truth that life is hard, and there are two options, either drown in the darkness or laugh around the campfire.

Sometimes the best you can do is let the good times roll.

11. Somewhere With You

Definitely one of the more painful songs on this list. The song is not afraid of talking about the pain one feels when they lose someone. Kenny Chesney is no stranger to expressing emotions.

The song expresses the feeling of caraphernelia, having to deal with the remains of a relationship, including memories.

12. Don’t Happen Twice

What does meeting a once extremely important person in your life again feel like? How weird is life that the person we once cherished immensely is now just another old friend? 

Kenny Chesney likes to talk about treasuring what you have before it is gone forever.

13. The Boys Of Fall

If you grew up playing football, you definitely know about this song. Not only does it talk about camaraderie, but it also paints a perfect picture of what it’s like on game day. Chesney himself loved football in high school.

To quote the singer’s thoughts on the game, “it’s life changing.”

14. Come Over

This song is Chesney’s remarkable 24th No. 1 hit. The beautiful song talks about two people who, although the relationship is broken, still find themselves running back together.

The singer described the lyrics as “incredibly universal” and is a very familiar situation to a lot of people.

15. American Kids

What is it like to be a true young American? “American Kids” is not just a song for the country, it’s a song for the youth. Chesney talks about the truths of life and what it’s like to work hard and persevere.

In Kenny Chesney’s words, it’s not a perfect world.

The American country superstar is known as one of the most successful crossover country artists with over 30 million albums sold around the world.

Kenny Chesney came to the aid of the victims of Hurricane Irma by setting up a charitable fund called “Love for Love City.”

Here are more classic Kenny Chesney songs to listen to – hear the life changing songs from a true country superstar:

  • Living In Fast Forward
  • You Had Me From Hello
  • No Shoes, No Shirt, No Problem
  • I Go Back
  • Beer In Mexico
  • Big Star
  • Anything But Mine
  • Everybody Wants to Go to Heaven
  • Who You’d Be Today
  • Better As A Memory

Feast your ears on the greatest Kenny Chesney songs ever.

Latest Stories

Dolly Parton speaks emotionally during an interview, sharing why she’s putting new songs on hold while grieving her husband Carl Dean.

Dolly Parton Says She’s Putting New Songs on Hold While She Grieves for Her Husband

Sometimes the queen of country needs a quiet moment, too. Dolly Parton has been writing songs longer than some of her fans have been alive, turning heartbreak, hope, faith, and ...

Kelly Clarkson sings passionately onstage in Vegas, fulfilling Dolly Parton’s special request with her stunning cover of “I Will Always Love You.”

Kelly Clarkson Grants Dolly Parton’s Special Song Request With Stunning “I Will Always Love You” in Vegas

Sometimes you just shut your mouth and do what the queen tells you to do. That’s exactly what Kelly Clarkson did when Dolly Parton herself slid into her Instagram comments ...

Miranda Lambert sings onstage in Miami wearing a cowboy hat and black shirt during her bittersweet tribute to her bandmate’s late father.

Miranda Lambert’s Bittersweet Miami Tribute to Bandmate’s Late Father Leaves Fans in Tears

Sometimes the moments that hit the hardest on tour don’t even happen under the spotlight. Miranda Lambert has spent the better part of two decades reminding country music what it ...

Florida Georgia Line’s Tyler Hubbard and Brian Kelley stand together at a bar amid speculation about whether the duo is done for good and what really happened between them.

Is Florida Georgia Line Done for Good and What Really Happened Between Tyler Hubbard and Brian Kelley?

Sometimes, the bigger the stage, the messier the backstory, and Florida Georgia Line has always been a prime example of that. When Tyler Hubbard and Brian Kelley first teamed up ...

Kane Brown performs onstage wearing a “FAMILY” hat, after revealing a songwriter once refused to work with him over his skin color but came back when he got famous.

Kane Brown Says Songwriter Refused to Work With Him Over Skin Color and Came Crawling Back When He Got Famous

Sometimes success tastes a little sweeter when you remember who shut the door on you in the first place. Kane Brown is no stranger to breaking records and topping charts, ...

Noah Cyrus stands on the Grand Ole Opry stage in a white lace dress, singing into a microphone with a drummer playing behind her.

Noah Cyrus Finally Makes Opry Debut on an Emotional Night She’ll Never Forget

Sometimes, a family name can open every door and still feel heavy as hell to carry once you step into the spotlight yourself. That’s what went down when Noah Cyrus ...

Travis Tritt smiles in a black cowboy hat and shirt while performing "Good Ol' Boys" with a microphone in front of an American flag backdrop.

Travis Tritt Honors Waylon Jennings With Cover of “Good Ol’ Boys” Theme From The Dukes of Hazzard

Sometimes a song is so tied to a legend that when someone else picks it up, you’re half ready to wince, but then Travis Tritt walks up, tugs his hat ...

Miranda Lambert and Chris Stapleton perform together in a bar setting for their duet “A Song to Sing.

Miranda Lambert and Chris Stapleton’s “A Song to Sing” Duet Feels Like an Instant Classic

Sometimes country music gives you a line so pure it feels like it’s been here forever, and that’s exactly what Miranda Lambert and Chris Stapleton just pulled off with “A ...

Blake Shelton and Noah Cyrus standing side by side with microphones, performing their new country duet together.

Noah Cyrus Teams Up With Blake Shelton for New Country Duet and Fans Are Loving It

Sometimes country music needs a little shot of something wild, and Noah Cyrus just poured it straight into Blake Shelton’s glass. It’s not every day you see the Voice coach ...

George Strait performing on stage with his guitar and cowboy hat, pictured at a previous event not related to the upcoming Strait From the Heart benefit concert.

George Strait Will Play “Strait to the Heart” Benefit Concert to Raise Money for Flood Victims

Some kings wear crowns, some kings wear boots, and show up when the water’s rising. George Strait, the King of Country himself, is stepping up once again for the people ...