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The 10 Best Kenny Chesney Songs

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With an incredible 16 studio albums, Kenny Chesney is one of the most prolific country superstars still at the top of his game. And when you pour over the track listing of any Chesney record, it’s no wonder that he is one of few artists in any genre who can sell out football stadiums.

Amazingly, the East Tennessee native already has two greatest hits albums under his belt, and he’s already due for a third. When great songs like “The Tin Man,” “She Thinks My Tractor’s Sexy,” “Summertime,” “Big Star,” “Beer In Mexico,” “Boston,” “Pirate Flag,” “Living In Fast Forward,” “Fall In Love,” “Grandpa Told Me So,” “From Hillbilly Hell To Honky Tonk Heaven,” “Guitars and Tiki Bars,” “Christmas In Dixie” and “California” don’t make the list, you know there’s a lot to choose from.

The self professed “island boy” who loves living in paradise also does a great job of singing great “life lesson” tunes. Let’s take a look at the top 10 Kenny Chesney songs.

10. “All The Pretty Girls”

Though a new addition to Chesney’s catalog — it’s his current single — “All The Pretty Girls” was an immediate hit and fan favorite. Buoyed by an infectious chorus and Chesney’s fantastic ability to capture the whimsy of American youth, the song just reached No. 1 on the chart. Cosmic Hallelujah features plenty of hits, including “Setting The World On Fire” featuring Pink, but “All The Pretty Girls” stands out as a rock n’ roll revival tune that will keep crowds singing along for years to come.

9. “No Shoes, No Shirt, No Problems”

It’s weird to think that Kenny Chesney’s “big break” came after he already had a greatest hits album. But truthfully, 2002’s No Shoes, No Shirt, No Problems is the record that really took him to the next level. It produced five top 5 singles, including the title track. The carefree tune helped solidify Chesney as the chancellor of chill. It also gave Chesney inspiration for his fan base name, “No Shoes Nation.”

8. “How Forever Feels”

Both Kenny Chesney and Tim McGraw cut this song, but only Chesney released it. And in 1999, it became the second No. 1 single of his career. The carefree tune that references both Jimmy Buffett and Richard Petty helped establish Chesney as a disciple of the former. Plus, he manages to make a song about chilling on a beach, driving fast cars and finally committing to a relationship. In the South, there are more than a few girls who love the sound of that.

7. “Old Blue Chair”

One of the few songs Chesney wrote by himself, “Old Blue Chair” appears on both 2004’s When The Sun Goes Down and his “side project,” 2005’s Be As You Are (Songs From An Old Blue Chair). The tune never got single treatment on either record (the latter wasn’t never actually meant to really be a “proper” release). But it’s one of Chesney’s most heartfelt songs, and being one of few penned entirely by himself, you know it means a lot to him. In fact, he even named his spirits company “Blue Chair Bay” and continually referenced the item in other songs.

6. “Don’t Blink”

Kenny Chesney has more than a few good “life lesson” songs and “Don’t Blink” from 2007’s Just As I Am: Poets & Pirates is up there with the best of them. It’s still tied for his fastest-rising single and even held the record for highest debut on the radio — for precisely one week. But the brilliant thing about the song is that it offers life advice without sounding too condescending. Instead of Chesney “imparting” this wisdom, he sings of an old man being interview on the TV. He relays the message to listeners, and to this day it’s one of country music’s more endearing messages.

5. “There Goes My Life”

“There Goes My Life” is probably the one song that best mixes clever wordplay and sweet sentiment. It takes a character who is positive his life is over when he founds out he’ll be a father unintentionally. But then throughout life realizes his life was really just beginning. It probably hits home with more than a few dads out there as a song that’s not too sappy but still hits the nail on the head.

4. “Somewhere With You”

“Somewhere With You” came from 2010’s Hemingway’s Whiskey, which was just a monster album. It featured “Boys Of Fall,” “Live A Little,” “Reality” and the third song on this list. But “Somewhere With You” was a notably different song for Chesney. The darker vibe of the song proved Chesney had more than “carefree island life” and “heartfelt advice” songs up his sleeve. In a lot of ways, he took a chance on the tortured song, and it paid off. Worth noting, too, is that “Somewhere With You” became Shane McAnally‘s first No. 1 single. It even made it to No. 15 on the Adult Contemporary charts.

3. “You and Tequila”

“You And Tequila” featuring Grace Potter is just downright one of the best country ballads in modern country. The song earned two Grammy nominations in the 54th Grammy Awards, one for Best Country Group/Duo Performance and one for Best Country Song. Chesney actually knew about the song all the way back in 2003, when it was written. But for whatever reason it took him seven years to release. Good thing he did. The single went platinum, despite not quite reaching No. 1 (it peaked at No. 3). He later collaborated with Potter again on “Wild Child.”

2. “American Kids”

Chesney’s catchiest song ever, “American Kids” is also his most-streamed song and the most successful from The Big Revival. Interestingly enough, he almost didn’t get a chance to record it. Little Big Town put the song on hold after they heard it. But songwriter Shane McAnally had actually sent it to Chesney first, he just didn’t get around to listening to it until much later. When he heard it, he absolutely loved it, and Little Big Town graciously gave it back to him. The song also proves that, despite being an elder statesmen of country now, Chesney still has a knack for capturing the intricacies of American youth.

1. “The Good Stuff”

The second single off his 2002 album No Shoes, No Shirt, No Problems, “The Good Stuff” is the quintessential Chesney song. It’s tied for his longest-running No. 1 country single and became the No. 1 country single for all of 2002. It also hit No. 22 on the Billboard Hot 100 chart. Featuring the favorite American trop of a wide bartender and some sage wisdom, nobody can make drinking a glass of milk at a bar as cool as Kenny Chesney.

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The 10 Best Kenny Chesney Songs