15 Top Kenny Chesney Songs Over 25 Years of Country Music

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:

Feast your ears on the greatest Kenny Chesney songs ever.