Over the last 24 years, country music superstar Kenny Chesney has released a whopping 63 singles to country radio. Most of these songs have been top 10 singles for Chesney, with 27 of which reaching the top of the charts. Another 15 have been top 5 singles (separate from the 27 Number Ones). His catalogue is impressive, to say the least. On October 27th, Kenny will release an album, titled ‘Live In No Shoes Nation,’ which will contain 30 tracks from his live performances.
With this album on the horizon and Kenny set to take over Gillette Stadium later this week, we’ve compiled our list of our 30 favorite singles that Kenny has released to country radio.
30.) ‘All The Pretty Girls’
Kicking off the list if Chesney’s most recent single, ‘All The Pretty Girls.’ The only thing working against this single is that it’s just so new. Released in June of this year, it needs more time to live up the other singles that have dominated country music airwaves over the years.
29.) ‘Me And You’
An oldie but goodie, ‘Me And You’ was released to country radio back in 1996. It’s one of the few ballads that made the list but what really sets it apart is the songwriting.
28.) ‘You Had Me From Hello’
Inspired by the film ‘Jerry Maguire,’ Kenny teamed up with Skip Ewing to write this single and released it in 1999. Another romantic ballad, ‘You Had Me From Hello’ is a single sure to pull on the heartstrings.
27.) ‘You Save Me’
The fourth single off ‘The Road And The Radio’ album, ‘You Save Me’ is another great ballad that reached the Number 3 spot on the charts back in 2006.
26.) ‘She’s Got It All’
This was Kenny’s first Number One single way back in 1997, 20 years ago! Need we say more!?
25.) ‘Reality’
Written by Kenny and his buddy Brett James, ‘Reality’ became Kenny’s 21st Number One song after he released it to radio in 2011. It’s an homage to live music as Kenny said, “I related it to everybody that comes to see us. That’s what live music is. It’s an escape from reality.“
24.) ‘Living In Fast Forward’
Chesney says the 2006 song “defines how I’ve lived my life in the last several years. Because it has happened so quick. And I say it’s happened so quick. I mean, I’ve been doing it for 12 years. But the last four to five years, it’s been an amazing thing to live through and to see happen to you and to see your fan base grow to a point where it’s unbelievable to stand in front of that microphone every night and see how passionate they are about your music. … More importantly, how much fun they’re having with it … out in the parking lots before the show and during the show. It’s everything I ever dreamed of and more.”
23.) ‘Bar At The End of the World’
One of Kenny’s recent singles, ‘Bar At The End of the World’ comes in at Number 24. We saw Kenny perform this one live in Tortuga and we fell even more in love with it. The catchy chorus is one that will get stuck in your head.
22.) ‘Don’t Blink’
We love this one. Time flies. Life is short. And this song encapsulates all that.
21.) ‘Setting The World On Fire’
Kenny has done his share of collaborations, but this one is one of our favorites as he brought in P!nk for this 2016 Number One hit.
20.) ‘Come Over’
We’re a little biased here. Back in 2013, fans serenaded Chesney with some extra ‘Whoa-oh-ohhh’s’ that made for one emotional moment at Gillette Stadium. One of those special moments for any artists where an entire stadium is singing back to you. But still, the sexy ‘Come Over’ is one of our favorite songs from Kenny.
19.) ‘Out Last Night’
Released in 2009, ‘Out Last Night’ is one of Kenny’s most playful and fun songs he’s released and became a fan-favorite because of that.
18.) ‘When The Sun Goes Down’
Kenny recruited his buddy Uncle Kracker for another great collaboration. This song, and title-track of his album, was released in 2004 and soon became another Number Song and Platinum-certfied single.
17.) ‘Til It’s Gone’
The second single off Kenny’s 2014 album titled ‘The Big Revival,’ and also the second of four Number One singles off that album, ‘Til It’s Gone’ has become a fan-favorite and one that always turns into a giant sing-along.
16.) ‘Anything But Mine’
Let’s go back to 2005 for this mid-tempo ballad off the ‘When The Sun Goes Down‘ album. This hit was released in January of 2005 and in April of that year, it reached the top of the chart!
15.) ‘Don’t Happen Twice’
Kenny’s first Number One single in the 21st century, ‘Don’t Happen Twice’ was released in 2001 from his ‘Greatest Hits‘ album.
And we can’t forget what Cole Swindell joined Kenny on stage a couple summers ago for this song!
14.) ‘Feel Like A Rock Star’
Featuring his Brother of the Sun, Mr. TIm McGraw, this song was especially fun live when the two co-headlined stadiums across the country on the Brothers of the Sun Tour in 2012. This was a Gold-certified single off his ‘Welcome to the Fish Bowl‘ album.
13.) ‘Somewhere With You’
It’s one of the relatively darker song for Kenny Chesney. But one that definitely resonated with his fans as the single soared to the top of the charts and was eventually certified Platinum by the RIAA!
12.) ‘I Go Back’
If you ever wanna reminisce, this song is for you. ‘I Go Back’ comes in at Number 12 on our list not only because of it’s musical value but it’s one of our favorite songs to see Kenny perform live.
11.) ‘She Thinks My Tractor’s Sexy’
Can never go wrong with this single from 1999!
10.) ‘How Forever Feels’
Here’s another pre-turn-of-the-century Number One single! Two Fun Facts: 1.) ‘How Forever Feels’ was also Kenny’s first Top 40 hit on the pop chart. 2.) Kenny almost didn’t get to release the song as Tim McGraw had cut it. Ultimately Tim didn’t release it and Kenny scooped it up quickly.
9.) ‘The Boys of Fall’
Kenny is a HUGE football fan which must make his near-annual stops at NFL football stadiums pretty special. It’s even more special for us New Englanders as he chooses to end his tours at Gillette Stadium every summer. And with the great success that our New England Patriots have had since 2001, it’s generally a great time for Kenny and the Kraft’s to bring out our several Lombardi trophies!
8.) ‘Young’
‘Young’ comes in at Number 8 on our list. It’s another classic single, one that was released back on New Year’s Eve of 2001! What a way to ring in the New Year!
7.) ‘Save It For A Rainy Day’
Number 7 on our list is ‘Save It For A Rainy Day’ – a single that was released in 2015. It comes in at this spot because of the songwriting, and content. And it doesn’t hurt that Kenny has brought Old Dominion on the road the last couple years which allows fans to see two of the songwriters, Matthew Ramsey and Brad Tursi (of Old Dominion) to come out on stage and perform the song with Kenny.
6.) ‘Never Wanted Nothing More’
Fun Fact: Did you know that Chris Stapleton (Yes, that Chris Stapleton) co-wrote this 2007 Number One single with Ronnie Bowman!?
5.) ‘No Shoes, No Shirt, No Problem’
This is one of the all time Kenny Chesney classics. A song that defines everything Kenny is. When he’s done with touring for the year, he jetsets down to the Caribbean for a winter on the beach. We all wish we could do the same!
4.) ‘Beer in Mexico’
Back in 2005, Kenny released his album, ‘The Road and the Radio.’ Over a year later, Chesney release ‘Beer in Mexico’ as the fifth and final single off this album and it’s been a staple on his setlist ever since.
3.) ‘American Kids’
We were hooked after the first listen of ‘American Kids’ when it was released in 2014. The melody is insanely infectious and always makes for great moments in his live performances!
2.) ‘Pirate Flag’
As we all know, Kenny is the leader of No Shoes Nation. His logo features this name as well as a skull and crossbones we’ve all come to know through pirate themes in pop culture. And this is a song that will always be one of our favorites. We love seeing all the Pirate Flags at his live shows and even more so when Kenny pulls one out of the crowd and waves it back and forth acknowledging his devout following!
1.) ‘Summertime’
What are the things that remind you of summer? One of the main things for us is Kenny! Maybe it’s his great music or maybe because his shows at Gillette Stadium usually signal the end of the summer. Either way, this song is everything that Kenny Chesney stands for! And that’s why it comes it at Number One on our list!