17 Best Kenny Chesney Songs
Contents
“Living In Fast Forward”

Song year: 2005
“Living in Fast Forward” leans toward Chesney’s rock-and-roll influence by adding more guitar, drums, and hard beats to the classic country style.
Its lyrics give listeners a glimpse into Chesney’s meteoric rise to stardom. When this song was released, the country singer had been performing for a decade but he was only thrown into the spotlight with his 2002 album All I Need to Know.
Chesney looks back on the changes to his life, and the privilege of singing in front of his passionate fans. This hit was released on The Road and the Radio, topping the Billboard Hot Country Songs chart and the Billboard 200 in 2005.
“Don’t Happen Twice”
Song year: 2001
This song is a meaningful tune about a person’s first love and how, although it may end, it has a lasting impact on their life. Chesney talks about how he fell in love with a girl as they were having a romantic evening with one another.
He states that no relationship can recreate falling in love for the first time. This song was written by Curtis Lance and Thom McHugh for Chesney’s Greatest Hits album.
“She’s Got It All”
Song year: 1997
“She’s Got It All” is a meaningful song, as it was Chesney’s first hit that topped the charts.
This romantic tune on Chesney’s I Will Stand album is a celebration of love. The upbeat melody blends well with the sweet, hopeful lyrics.
In this song, the narrator is a man who spent his days dreaming and praying he’d find the perfect woman to devote his life to. Eventually, he finds someone who embodies everything he ever wanted, and now he can’t believe he gets to give her all his love.
“Setting the World on Fire”
Song year: 2016
This song, written by Matt Jenkins, Josh Osborne, and Ross Copperman, was a collaboration between Chesney and pop star Pink.
Released in July 2016 as a country-pop crossover, it earned top spot on the Canadian Country on Billboard, US Hot Country Songs, and US Country Airplay. The lyrics were inspired by Osborne’s time spent partying with his wife on a trip to Los Angeles to attend the Grammys.
“The Boys of Fall”
Song year: 2010
“The Boys of Fall” was written by Dave Turnbull and Casey Beathard for Chesney’s 2010 album, Hemingway’s Whiskey. Chesney takes a close look at small town America, exploring how one community revolves around football, high school life, and other “traditional” aspects of life in the US.
In keeping with its themes, Chesney recorded the music video in Celina High School and other schools/colleges in the southern United States. The song reached number one on the US Hot Country Songs Charts and Canady Country Charts Billboard.
“Out Last Night”
Song year: 2009
“Out Last Night” was written by Kenny Chesney and Brett James on Chesney’s Greatest Hits II album. This energetic country song revolves around a man looking back at a raucous party he and his friends attended. The man recalls the people he met, how he acted, and what it felt like to meet the rich and famous.
The music video was filmed at Raleigh Hotel on South Beach. “Out Last Night” topped the US Hot Country Songs and Canada Country Songs on Billboard. It also reached 16th on the US Billboard Hot 100 in 2009.
“Better as a Memory”
Song year: 2008
“Better as a Memory” is a song written by Lady Goodman and Scooter Carusoe that was released in 2008 for Chesney’s Just Who I Am: Poets & Pirates album.
Typical of many country ballads, this record centers around a man splitting up with someone because he doesn’t want to be in a serious relationship. Its moving lyrics suggest the man has a habit of breaking up with people. In the end, the narrator says he’s better being someone’s memory than their boyfriend.
This song got to number one in the US Billboard Hot Country Songs and came second on the Canadian Country charts.
“Everybody Wants to Go to Heaven”
Song year: 2008
Interestingly, “Everybody Wants to Go to Heaven” was originally meant for the legendary George Strait. However, when he passed it over, Chesney scored a number one hit with it when included it on his own album, Lucky Old Sun.
The song was written by Jim Collins and Marty Dodson, featuring a more reggae, calypso, and mid-tempo melody instead of the traditional country or rock style that Chesney typically used in the 2000s. However, like many country songs, it has religious overtones. In this instance, the song is sung from the perspective of a man opening about his life of excess to a preacher.
“Down The Road”
Song year: 1990/2008
“Down the Road” appeared on the 2008 album, Lucky Old Sun, as a duet with Mac McAnally. It was an immediate hit, topping the country charts in 2009 and being nominated for a Grammy for Best Country Collaboration with Vocals.
Chesney’s track, which received positive reviews from critics, is a sympathetic tale of young love hampered by a girl’s parents who do not want the main protagonist to date their daughter. As the song progresses, we follow the narrator as they navigate the same troubles with their own kid.
Top Kenny Chesney Songs, Final Thoughts
Kenny Chesney is a talented musician, singer, and songwriter who has put out chart-topping albums and singles. Over his long career, he has continued to release and collaborate with other artists to create soulful ballads, upbeat country songs, and pop-country crossovers.
While these songs are considered among the best Kenny Chesney songs, the singer has a long discography spanning several decades. Let us know which is your favorite.