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 pore over the track listing of any Chesney record, it's no wonder that he is one of few artists in any genre who's sold out football stadiums across multiple decades.
Chesney emerged in the '90s and suited the hat act moment. Like peer Tim McGraw, Chesney has remained relevant past age 50 by changing with the times without those changes overshadowing the elements that initially made him a star. Such a feat's rare in a genre that historically moves on from even its biggest stars before they turn 40, relegating them to living legend status instead of positioning them continued cultural relevancy.
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 20 great Chesney songs.
Tim Mosenfelder/Getty Images Chesney's voice -in the singer and storyteller senses- suited '90s trends just as smoothly as it flows with his 21st century material. For instance, revisit this well-produced fiddle tune that's one of several love songs in his repertoire that holds up against similar works by Toby Keith and others. Rusty Russell/Getty Images A much more recent selection, "Happy Does" reminds us — not that true fans need it— that Chesney's good for more than feel-good beach day jams. One of his many songs about enjoying the simpler things in life, it's a solid example of the world-building character studies mastered by some of Music Row's elite wordsmiths. M. Caulfield/WireImage for American Music Awards A staple of Chesney's steel drum-accompanied odes to the Salt Life, "When the Sun Goes Down" pairs the country mainstay with an under-appreciated vocalist in Uncle Kracker. It's one of several collaborations worth of list consideration. Ron Wolfson/WireImage for Bragman Nyman Cafarelli An album we'll revisit often, 1999's Everywhere We Go established Chesney as a superstar with staying power. In addition to its career-affirming singles, there's this soul-stirring gospel song that pairs Chesney with the master of such material, Randy Travis. Theo Wargo/WireImage Chesney embraces the Y2Country flavor of rock-infused twang, and of course, he proves to be as good at it as any of the artists he helped inspire. The banjo accompaniment's very Keith Urban, and that's a good thing. Plus, it's nostalgic theme is both heartwarming and, for many from small towns, relatable. Jason Koerner/Getty Images "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 hit 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. Jason Squires/WireImage 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 his highest debut on country radio. 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 interviewed on the TV. Through those means, he relays the message to listeners. Beth Gwinn/Getty Images Both Chesney and 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. Chris Polk/FilmMagic One of the few Kenny Chesney songs he wrote solo, "Old Blue Chair" appears on both 2004's When The Sun Goes Down and 2005's Be As You Are (Songs From An Old Blue Chair). The tune never got single treatment on either album— the latter wasn't never actually meant to really be a "proper" release). He named his spirits company "Blue Chair Bay" and continually referenced the item in other songs. Ebet Roberts/Redferns via Getty Images "You And Tequila" featuring Grace Potter is downright one of the best 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 knew about the song all the way back in 2003, which is the year it was written. But for whatever reason it took him seven years to release it. The single went platinum, despite not quite reaching No. 1 (it peaked at No. 3). He later collaborated with Potter again on "Wild Child." Rick Diamond/WireImage A longtime fan favorite and live set staple, "Beer in Mexico's" a fast-driving singalong that trails only "No Shoes, No Shirt, No Problem" in the pantheon of Chesney's cowboy beach bum jams. Rick Diamond/Getty Images A rocking tune that lands somewhere between Tom Petty and Big & Rich, "Pirate Flag's" a stadium stomper that's among the best examples of Chesney's vocal versatility. Plus, it furthers his beach-loving country troubadour image. Beth Gwinn/Getty Images While most of Chesney's best-known songs are no laughing matter, one of the songs that signaled his mainstream arrival is tongue-in-cheek, to put it lightly. "She Thinks My Tractor's Sexy" added to the near-endless playlist of light-hearted '90s country jams while establishing Chesney as someone who can make a wide range of stories compelling. Christopher Polk/Getty Images for dcp Chesney's catchiest song yet, "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 the quartet heard it. But songwriter McAnally had actually sent it to Chesney first, with the singer not getting around to listening to it until much later. When Chesney 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 statesperson of country now, Chesney still has a knack for capturing the intricacies of American youth. Paul Natkin / Contributor "Somewhere With You" came from 2010's Hemingway's Whiskey, which was 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. Its darker vibe 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 the first No. 1 penned by prolific Nashville songwriter Shane McAnally. It even made it to No. 15 on the Adult Contemporary charts. Gina Ferazzi/Los Angeles Times via Getty Images It's strange to think that Chesney's "big break" came after he already had a greatest hits album. However, it's 2002's No Shoes, No Shirt, No Problems that 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." Tim Mosenfelder/Getty Images One of the ultimate wedding dance or promposal tunes of its time, "You Had Me From Hello" replicates the feeling of that moment when someone falls in love— and, more rewardingly, the series of events that prove it's a love made to last. This Chesney co-write with Skip Ewing could've been a hit for any number of artists in just about any decade. Paul Hawthorne/Getty Images "There Goes My Life" is the best Chesney song that best mixes clever wordplay and sweet sentiment. It takes a character who is positive his life is over when he finds out unexpectedly that he'll be a father. But over time he realizes that 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 goes right for the heartstrings. Paras Griffin/Getty Images In one of the best examples of Chesney changing with the times, this Chesney standard about appreciating the simple things in life sounds as much like a Mumford and Sons-style indie-pop crowd-pleaser as it sounds like the surefire country radio hit it proved to be in short order. Rusty Russell/Getty Images "The Good Stuff" remains the quintessential song from Chesney. It's tied for his longest-running No. 1 and became the top country single for all of 2002. It also hit No. 22 on the Billboard Hot 100 chart. Featuring the favorite American trope of a wise bartender and some sage wisdom, nobody can make drinking a glass of milk at a bar as cool as Chesney can."She's Got It All" (I Will Stand, 1997)
"Happy Does" (Here and Now, 2020)
"When the Sun Goes Down" (Feat. Uncle Kracker) (When the Sun Goes Down, 2004)
"Baptism" (Feat. Randy Travis) (Everywhere We Go, 1999)
"I Go Back" (When the Sun Goes Down, 2004)
"All The Pretty Girls" (Cosmic Hallelujah, 2017)
"Don't Blink" (Just As I Am: Poets & Pirates, 2007)
"How Forever Feels" (Everywhere We Go, 1999)
"Old Blue Chair" (Be as You Are, 2005)
"You and Tequila" (Feat. Grace Potter) (Hemingway's Whiskey, 2010)
"Beer in Mexico" (The Road and The Radio, 2005)
"Pirate Flag" (Life on a Rock, 2013)
"She Thinks My Tractor's Sexy" (Everywhere We Go, 1999)
"American Kids" (The Big Revival, 2014)
"Somewhere With You" (Hemingway's Whiskey, 2010)
"No Shoes, No Shirt, No Problems" (No Shoes, No Shirt, No Problem, 2002)
"You Had Me From Hello" (Everywhere We Go, 1999)
"There Goes My Life" (When the Sun Goes Down, 2004)
"Get Along" (Songs For the Saints, 2018)
1. "The Good Stuff" (No Shoes, No Shirt, No Problem, 2002)
Editor's Note: This article was originally published in 2017. It was expanded in Aug. 2023.
