17 Best Kenny Chesney Songs

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”

Song year:

“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.

“Come Over”

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.