Kenny Chesney has been releasing albums for over 25 years and just announced the Deluxe Version of his 2020 Here and Now album and there is no sign of the superstar stopping anytime soon. Next year, he’ll be on the road: he just pushed his next stadium tour to 2022.
It’s not easy to rate all of Kenny’s singles and everyone’s list would be different: lists are, of course, subjective. But having interviewed Chesney and talked music with him since his debut album was released in 1994, I am going to take a crack at it.
Here is my list of Kenny Chesney’s top 20 songs.
Kenny Chesney’s 20 Best Songs, Ranked
20. "Everybody Wants to Go to Heaven" with the Wallers (2008) - The song was initially to have been recorded by George Strait for his 2008 album ‘Troubadour,’ but after Strait decided not to include the song on this album, it was recorded by Kenny Chesney instead.
19. "Come Over" (2012) - I just love the smoothness of this song. It was written by Sam Hunt, Shane McAnally, and Josh Osborne.
18. "El Cerrito Place" (2012) – A solid story song originally recorded by Charlie Robison; Kenny put it on his 2012 album Welcome to the Fishbowl.
17. "American Kids" (2014) – Chesney heard the song during a writers' retreat with Mac McAnally, and said, "It was unlike anything I'd ever heard... it just grabs you and holds on, but even more importantly, it feels really good.”
16. "Wild Child" (featuring Grace Potter) (2015) – The song finds its narrator falling for a strong and independent woman, whose spirit is free and whose nature is rebellious.
15. "Setting the World on Fire" (with Pink) (2016) – A great collaboration with Pink, it was nominated for the Best Country Duo/Group Performance at the 2017 Grammy Awards.
14. "Everything's Gonna Be Alright" (with David Lee Murphy) (2017) – A collaboration between two longtime friends, it reached number one on the US Billboard Country Airplay chart, becoming Murphy's first number one since 1995's "Dust on the Bottle."
13. "The Good Stuff" (2002) – Simply a classic. The song became Chesney's fifth number one hit on the US Billboard Hot Country Singles & Tracks charts, At the time, it was also his longest-lasting number one, having spent seven weeks at that position.
12. "No Shoes, No Shirt, No Problems" (2003) – A song so good he named his fanbase – the No Shoes Nation – after it.
11. "When I Close My Eyes" (1996) – Already having been recorded by a couple of under-the-radar country artists, Chesney recorded it on his 1996 album, ‘Me and You.’
10. "Feel Like a Rock Star" (featuring Tim McGraw) (2011) – Friends for years since they both first came to Nashville; this was a great teaming of McGraw and Chesney and is one of my favorites.
9. "Shiftwork" (featuring George Strait) (2007)– It’s hard not to love anything with George Strait’s name attached and this is just a solid song. It was released in December 2007 as the third single from Chesney's 2007 album, Just Who I Am: Poets & Pirates.
8. "Happy Does" (2020) - One of Kenney’s latest singles from his Here and Now album, it’s the perfect song to brighten you up after a hard year in 2020.
7. "Here and Now" (2020) – Kenny was right on the money when he said of this song, “The chorus is everything I feel about my time on stage... the rush of it absolutely being the best place, best moment in the entire world. There’s no rush like it...It says everything about how we all put off living our lives because there’s so much other stuff to do."
6. "The Boys of Fall" (2010) - The song is about playing high school football, and Chesney says it "is a perfect description of how I grew up and where I grew up." That would be near Knoxville, Tennessee and UT football.
5. "She Thinks My Tractor's Sexy" (1999) - The song that brought him to the dance of country music stardom and had a big part in kicking off his huge career.
4. "How Forever Feels" (1998) - Chesney said at the time that he almost didn't get to release the song because Tim McGraw had recorded a version. McGraw decided not to release it, and after Chesney's version hit number-one, McGraw told him "I'm glad you cut it. It just didn't work for me."
3. "You Had Me from Hello" (1999) – Kenny saw the movie Jerry Maguire and in one of the film's most memorable scenes at the end of the movie, Tom Cruise's title character gives out a heartfelt talk to Renée Zellweger's character, tearfully saying, "You had me at 'hello.'" Chesney liked that line and decided to write a song based on it.
2. "You and Tequila" (featuring Grace Potter) (2011) – A classic and a beautiful song. The song received two nominations in 54th Grammy Awards for Best Country Song and Best Country Duo/Group Performance.
1. "The Tin Man" (1994) – This is a no-brainer for me the story and sentiment of “The Tin Man” speaks for itself. The ballad is about a brokenhearted man who wishes that he were the Tin Woodman so that he "wouldn't have a heart" and thus not feel the emotions that he is feeling.