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The essential Kenny Chesney playlist
Catherine Powell/Getty Images for Kenny Chesney

The essential Kenny Chesney playlist

Kenny Chesney has been a stalwart of the country music scene for nearly three decades. Thanks to his breezy, beachy vibe and seriously devoted fan base, Chesney's one of the genre's most successful artists, charting a whopping 31 No. 1 singles throughout his career. 

Flip through the slideshow below for 20 essential Kenny Chesney tracks, from early deep cuts like "The Tin Man" to major hits "She Thinks My Tractor's Sexy" and "Beer In Mexico." 

 
1 of 20

"She Thinks My Tractor's Sexy"

"She Thinks My Tractor's Sexy"
Tim Mosenfelder/Getty Images

The song that many fans associate with Kenny Chesney is "She Thinks My Tractor's Sexy." The track appeared on his fifth full-length album, Everywhere We Go. The cheeky ode to the appeal of a John Deere was a crossover success, even earning a spot on the Billboard Hot 100. 

 
2 of 20

"She's Got It All"

"She's Got It All"
Tim Mosenfelder/Getty Images

Released in 1997, "She's Got It All" was the first of many No. 1 hits on the Billboard Hot Country Songs chart for Kenny Chesney. 

 
3 of 20

"Better As A Memory"

"Better As A Memory"
Paul Natkin/WireImage

Released in 2008, "Better As A Memory" was hailed by many critics as one of Kenny Chesney's best vocal performances. It was one of the top country songs of that year, landing at No. 23 on the Billboard year-end chart. 

 
4 of 20

"You Had Me From Hello"

"You Had Me From Hello"
Paul Natkin/Getty Images

Kenny Chesney was inspired by the performance of his future wife, Renee Zellweger, in Jerry Maguire to write "You Had Me From Hello." Even though the couple's marriage was pretty short-lived, the song still powered to No. 1 on charts in the United States and Canada. 

 
5 of 20

"The Good Stuff"

"The Good Stuff"
Vince Bucci/Getty Images

Released in 2002, "The Good Stuff" is a song about making sure that you've got the right priorities in life. Its story follows a man who sidles up to a bar after a fight with his wife, asking for "the good stuff," meaning liquor. But the bartender schools the man on the actual good stuff in life — making memories with family. 

 
6 of 20

"Summertime"

"Summertime"
Ethan Miller/ACMA/Getty Images for ACMA

This 2007 anthem to warm summer days is still one of the best songs to play at your backyard barbecue. It's an ode to the simple pleasures of summertime, from "two bare feet on the dashboard" of an old Ford truck to an ice-cold swimming hole. 

 
7 of 20

"No Shoes, No Shirt, No Problem"

"No Shoes, No Shirt, No Problem"
Mike Coppola/Getty Images for SiriusXM

"No Shoes, No Shirt, No Problem" is probably the official anthem of No Shoes Nation, the moniker for Chesney's massive — and devoted — fan base. The beachy tune doubles as an ethos and song. "Want a towel or a chair, in the sand by the sea, wanna look through my shades, and see you there with me," Chesney sings. "Wanna soak up life for a while and lay back low." 

 
8 of 20

"I Lost It"

"I Lost It"
Beth Gwinn/Getty Images)

Featuring powerful harmonies with Kenny Chesney and Pam Tillis, "I Lost It" was a top-10 hit for Chesney in 2000, and it remains a favorite among his most devoted fans. 

 
9 of 20

"How Forever Feels"

"How Forever Feels"
Tim Mosenfelder/Getty Images

"How Forever Feels," an anthem about finding somebody to spend your life with, was released on Chesney's 1998 album Everywhere We Go.

 
10 of 20

"Get Along"

"Get Along"
Leigh Vogel/Getty Images for RFK Human Rights

This 2018 Chesney hit encourages everyone to find a bit of common ground amidst divisive times. It's also packed with solid life advice: "Paint a wall, learn to dance / Call your mom, buy a boat, drink a beer, sing a song." 

 
11 of 20

"You And Tequila," with Grace Potter

"You And Tequila," with Grace Potter
Photo by Rick Diamond/Getty Images

Kenny Chesney teamed up with powerhouse vocalist Grace Potter for "You and Tequila," a ballad about the worst kind of love-hate infatuation. Potter and Chesney harmonize beautifully on the tune, propelling it to crossover success on the pop and country charts. 

 
12 of 20

"When I Close My Eyes"

"When I Close My Eyes"
Photo by Tim Mosenfelder/Getty Images

This emotive ballad, centered around a man devoted to his lost love, hit No. 2 on the Billboard Hot Country Songs chart in 1996. 

 
13 of 20

"Don't Blink"

"Don't Blink"
Tim Mosenfelder/Getty Images

"Don't Blink" is another song in Chesney's catalog that speaks to the importance of family. Released in 2007 on Just Who I Am: Poets and Pirates, it earned equal praise from fans and critics.

 
14 of 20

"The Tin Man"

"The Tin Man"
Paul Natkin/WireImage

An early indication of Chesney's powerhouse vocals and writing prowess, "The Tin Man" was the second single from his 1994 debut album, In My Wildest Dreams. It only reached No. 19 on the Billboard Hot Country Songs chart, but "The Tin Man" helped fans notice an artist who would eventually become one of the genre's brightest stars. 

 
15 of 20

"Don't Happen Twice"

"Don't Happen Twice"
Kevin Winter/ACMA/Getty Images for ACMA

This upbeat track about love at first sight features Chesney at the height of his powers in 2001. The song appears on Chesney's first Greatest Hits compilation. 

 
16 of 20

"Who You'd Be Today"

"Who You'd Be Today"
Ron Wolfson/WireImage for Bragman Nyman Cafarelli

In 2005, Chesney released this heartbreaking tune about imagining the future of a person who died young. Despite its heavy subject matter, "Who You'd Be Today" remains a fan favorite thanks to Chesney's powerful vocal performance. 

 
17 of 20

"There Goes My Life"

"There Goes My Life"
Dan MacMedan/WireImage

This 2003 hit tells the story of a man who unexpectedly finds out he's going to be a father. The song tracks his journey from being initially disappointed about the news to growing into a proud father watching his child go off to college. 

 
18 of 20

"When The Sun Goes Down"

"When The Sun Goes Down"
Rick Diamond/Getty Images for Kenny Chesney

This 2004 mega-smash was a collaboration between Chesney and Uncle Kracker, all about partying by the beach. The song has since sold more than one million copies, earning it a Platinum certification from the Recording Industry Academy of America. 

 
19 of 20

"Beer In Mexico"

"Beer In Mexico"
J.Sciulli/WireImage for CMT: Country Music Television

His first No. 1 hit as a solo songwriter, 2005's "Beer in Mexico" was a wildly popular radio hit that same year. According to Chesney, he wrote it while vacationing in Cabo San Lucas and watching the waves — presumably with a cold one on hand. 

 
20 of 20

"The Boys of Fall"

"The Boys of Fall"
Frederick Breedon/FilmMagic

This song, about the South's obsession with high school football, is nostalgic for Chesney. "The Boys of Fall" peaked at No. 1 on the Hot Country Songs chart in 2010. It was the first single from his album Hemingway's Whiskey, and it's a tribute to his own love for the game. 

Amy McCarthy

Amy McCarthy is a Texas-based journalist. Follow her on twitter at @aemccarthy

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