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

Blake Shelton to host the Grand Ole Opry's 100th celebration, honoring a century of country music with star-studded performances.

Blake Shelton Set to Host Grand Ole Opry’s 100th Celebration

Country music’s most legendary stage is set for a once-in-a-lifetime celebration. Blake Shelton is taking the reins. The Grand Ole Opry will mark its 100th anniversary with a star-studded NBC ...

Dolly Parton fights to save her Imagination Library in Indiana after budget cuts threaten its vital funding for children's literacy.

Dolly Parton Fights to Save Imagination Library in Indiana

Dolly Parton has always stood up for what she believes in—lifting people’s spirits with her music, funding major charitable efforts, and ensuring children have access to books, no matter their ...

Billy Currington maintains a private personal life, sparking speculation about his sexuality, though no public statement or evidence confirms the rumors.

Is Billy Currington Gay? What We Know About the Country Star

Billy Currington has spent decades serenading country music fans with hits like “People Are Cr𝐚zy” and “Must Be Doin’ Somethin’ Right.” His smooth vocals, laid-back charm, and undeniable talent have ...

Post Malone and Alan Jackson pose together, bridging generations of country music with their iconic styles and shared respect for the genre.

Post Malone’s Road to Country Music Started Long Ago

Post Malone didn’t just wake up one morning and decide to go country—he’s been headed down this dirt road for a long time. From his Texas roots to his early ...

Drake sparks speculation about a country music crossover, potentially releasing a country album and exploring a new genre.

Is Drake the Next Artist to Take Over Country Music?

Country music has been through a wave of change lately, and not everyone is convinced it’s for the better. Beyoncé’s Cowboy Carter shook the industry, bringing country into the mainstream ...

Riley Green's 'Worst Way' music video sparks a frenzy with steamy scenes and a touch of humor, making waves in the country music world.

Riley Green Turns Up the Heat in Worst Way Music Video

Riley Green isn’t holding back in his latest music video for “Worst Way,” and fans are feeling some kind of way about it. Known for his rugged country charm and ...

Meet Lainey Wilson's fiancé, Devlin 'Duck' Hodges—former NFL quarterback and avid duck hunter—who captured the country star's heart.

Who Is Devlin ‘Duck’ Hodges? Meet Lainey Wilson’s Fiancé

Lainey Wilson is one of the biggest stars in country music right now. Still, behind the scenes, she has a steady and supportive partner in her fiancé, Devlin “Duck” Hodges. ...

Lainey Wilson announces her engagement to Devlin 'Duck' Hodges, sharing romantic proposal photos that celebrate their new chapter together.

Lainey Wilson Is Engaged to Former NFL Star Duck Hodges

Lainey Wilson has a lot to celebrate—her career is on fire, she’s gearing up for a massive world tour, and now, she’s engaged to her longtime boyfriend, former NFL quarterback ...

George Strait and Chris Stapleton announce their 2025 stadium tour, bringing country music fans an unforgettable live experience with special guests Parker McCollum and Little Big Town.

George Strait and Chris Stapleton Announce 2025 Stadium Tour

Country music fans, get ready—George Strait and Chris Stapleton are hitting the road again for another epic stadium tour. After a wildly successful run in 2023, the two country powerhouses ...

Chris Stapleton announces his retirement from singing the national anthem after his iconic 2023 Super Bowl performance, a moment destined to stand the test of time.

Chris Stapleton Is Officially Retired From Singing the National Anthem

Chris Stapleton’s unforgettable 2023 Super Bowl performance of The Star-Spangled Banner remains one of the greatest renditions in history. But if you hope to hear him take on the anthem ...