Kenny Chesney is one of the biggest country music stars of our generation. His style has changed many times over his career, alternating between traditional country, rock, pop, and reggae.
This article will introduce some of the best Kenny Chesney songs ever.
“There Goes My Life”
Song year: 2003
“There Goes My Life” is a romantic song about young love and teenagers who find out the course of their lives is derailed by an unexpected pregnancy.
Once the boy discovers his girlfriend is expecting a child, he has to come to terms with the news and grapple with how this life-changing event will alter the course of their life. They had dreams of leaving town and heading toward the coast. Instead, he faces the prospect of an unsatisfying life stuck somewhere he doesn’t want to be.
As the song progresses, the narrator marries the girl and realizes how much he loves his daughter. Poignantly, “There Goes My Life” ends with his daughter fulfilling her father’s dream – moving to the West Coast.
This hit song was featured on Chesney’s album When the Sun Goes Down, his eighth album, and spent weeks at the top spot in 2003 and 2004.
“Don’t Blink” is a tale of not missing out on the good parts in life as life goes fast. Kenny sings of talking to a 102 year old man and asking him for advice. The advice he receives is ‘don’t blink’.
The man then goes on to tell about how life jumps fast. This song is a good reminder to enjoy the journey along the way.
Song year: 2012
“Come Over” was a popular single written by Sam Hunt, Shane McAnally, and Josh Osborne that was released on Chesney’s 14th album, Welcome to the Fishbowl. This ballad reflects on a romantic relationship in Chesney’s life that transformed from a casual one-night stand into something more meaningful.
Chesney describes the loss of love and how relationships can change over time. The song's narrative explores how two people who are not developing within their relationship realize they might not be compatible with one another. However, their love makes them unwilling to break things off.
Many listeners can relate to this song, as it describes the hard times of being stuck between knowing what is best for you and following what your heart wants.
“The Good Stuff”
Song year: 2002
The Good Stuff was Kenny Chesney’s fifth charting hit. Its premise is centered on a man grieving the loss of his true love, his wife, and those who like to go against the grain and do things ‘out of the norm.’ The protagonist challenges the overarching idea of “the good stuff,” or traditional occurrences, that happen in life.
Chesney was inspired to write this melancholic song after his friend and security guard lost his wife to cancer.
“Somewhere With You”
Song year: 2010
“Somewhere With You” is a song by J.T. Harding, and Shane McAnally was the second single from Chesney’s 2010 album, Hemingway’s Whiskey. This song topped the U.S. Billboard Hot Country Songs chart in 2011.
This song differs from Chesney’s typical country music. Its lyrics focus on someone stuck between staying in their relationship or moving on. This song describes how, sometimes, couples suffer from bad timing and don’t work out in the long run.
Chesney topped the country charts in Canada and the US, and went 3x Platinum.
“You Had Me From Hello”
Song year: 1999
“You Made Me From Hello,” the second single from Kenny Chesney’s album, Everywhere We Go, marked a shift in style. Although Chesney started solely as a country singer, his musical experimentation moved him into an entirely new pop-country genre.
Chesney based the song around a line spoken by Tom Cruise’s character from the infamous movie Jerry Maguire. “You Had Me at Hello” is spoken by Cruise towards his onscreen love, played by Renee Zellwegger. Interestingly, Chesney would go on to marry the actress in 2005.
Despite being a pop-country mash-up, this hit single topped the Billboard Hot Country Songs chart in 1999.
“Who You’d Be Today”
Song year: 2005
This hit song debuted on The Road and the Radio, Chesney’s tenth album. When released, “Who You’d Be Today” became Chesney’s best performing song up to that point when it hit number 26 in the U.S. Billboard Hot Country Songs
Its romantic words, slow ballad style, and deep meaning have made it popular with country fans, although Chesney opted against including it in his Greatest Hits II album.
The song focuses on a narrator who misses someone who lost their life at a tragically young age. He reflects on their friendship and memories, and wonders what life would have had in store for them if they had lived. This bittersweet song ends on a poignant note, as the narrator notes they’ll be reunited one day.
“Never Wanted Nothing More”
Song year: 2007
If you’re more accustomed to Chesney’s slow and ballad-like songs, give “Never Wanted Nothing More” a listen for something a little different.
This uptempo song gives the listener a view of Chesney’s earlier life and the “firsts” of everything. Chesney describes the highs and lows of his first marriage, how he found his faith and religion, and the joys of buying his first car.
The song, which was included in Chesney's pop-country album Who I Am: Poets & Pirates, topped the country chart.
“Tip Of My Tongue”
Song year: 2020
Chesney collaborated with “Tip Of My Tongue” with two of the biggest names in the industry, singer Ed Sheeran and songwriter Ross Copperman.
While it might have surprised a few when released, the collaboration reflects Chesney’s willingness to experiment with his music and go beyond the ballads he’s famed for.
This song appears on Here and Now, and explores the importance of love, connection, and romantic relationships.
“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.