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Top 10 Kenny Chesney Songs

Kenny Chesney
Ethan Miller, Getty Images

The best songs that didn’t make this Top 10 Kenny Chesney Songs list would be better than 95 percent of similar lists for other artists. With 21 No. 1 hits and a seven-year span in which the singer never left the Top 5, Chesney is arguably the top country artist of the last 20 years. Which song do you think should be the No. 1 Kenny Chesney song of all time?

Our No. 1 landed at No. 29 on a list of the Top 100 Country Songs ever. Making up this list are ACM and CMA winners, and at least one song that was nominated for a Grammy Award. Most importantly, they’re the songs fans turn out by the thousands to see performed live every summer. Rockers like “Young” make the Top 10, as do ballads like “There Goes My Life” and more recent hits like “Come Over.”

You won’t find songs like “The Boys of Fall,” “I Go Back” and “Somewhere With You” on this list of Top 10 Kenny Chesney songs. They’re certainly worthy, but what songs should they replace? After some arguing, crying and banging of heads against the wall, we settled on these 10.



From ‘No Shoes, No Shirt, No Problems’ (2002)



Kenny Chesney’s career really skyrocketed after the release of the No Shoes, No Shirt, No Problems album in 2002. Two songs from that project make the Top 10 Kenny Chesney Songs list, while three others — like the title-track and “Big Star” — could have. “Young” celebrates the freedom of youth that we all have lived at some point. This song was a Top 5 hit for Chesney.



‘How Forever Feels’

From ‘Everywhere We Go’ (1999)



It was difficult to choose between “How Forever Feels” and “She’s Got It All,” two early chart-toppers for Kenny Chesney. Both songs share a style that dominated so much of the singer’s late-90s music, but we ultimately put “How Forever Feels” at No. 8 on the Top 10 Kenny Chesney Songs list due to its slightly stronger lyrical content. How can you say no to a song that name-checks Jimmy Buffett and Richard Petty? “How Forever Feels” is the oldest song on this list.



‘The Good Stuff’

From ‘No Shoes, No Shirt, No Problems’ (2002)



Song No. 7 is another from No Shoes, No Shirt, No Problems. “The Good Stuff” is perhaps the strongest story in the singer’s repertoire. Stripped down production allows one to enjoy each word of his story, while letting the overall message sink deep into the soul. It would likely end up higher on this list of Kenny Chesney’s Top Songs, but its sales numbers were not as impressive as a few others.



‘When the Sun Goes Down’

From ‘When the Sun Goes Down’ (2004)



This is the first of three tracks from When the Sun Goes Down to make the Top 10 Kenny Chesney Songs list. Chesney doesn’t do many duets, but this one is his best by far. His chemistry with Uncle Kracker was as much fun to listen to as the hooky chorus and cheeky message. The early-to-mid-2000s were Chesney’s finest years. Everything he touched turned to gold, including this song, which went gold for selling more that 500K singles.



‘Anything But Mine’

From ‘When the Sun Goes Down’ (2004)



This gold record was the fifth of six singles from the When the Sun Goes Down album, which proves how strong the 2004 project was. Short-term love is a theme the singer comes back to regularly throughout his career — most recently on “Come Over.” One wonders if these sorts of songs are honest revealings of the very private life he lives offstage. “Anything But Mine” was a staff favorite on this list of the Top 10 Kenny Chesney Songs.



‘Come Over’

From ‘Welcome to the Fish Bowl’ (2012)



Kenny Chesney has taken to revealing his vulnerabilities in recent years, and perhaps no song is as raw as “Come Over,” a No. 1 from 2012. The single went Platinum, and was accompanied by an effective music video. Much like “You and Tequila,” this song takes time to soak in, but true Chesney fans know it to be amongst his best songs ever.



‘Don’t Blink’

From ‘Just Who I Am: Poets & Pirates’ (2007)



Chesney’s genius is that he can mix up carefree party songs with emotional ballads like “Don’t Blink,” song No. 5 on the Top 10 Kenny Chesney Songs list. This song forces one to think of the greater meaning of life, while encouraging you to live each day to its fullest. It scores strong points for lyrical quality and story-telling. “Don’t Blink” was a No. 1 song for Chesney in 2007 — in fact, it was the fastest-rising No. 1 single of his career.



‘You and Tequila’

From ‘Hemingway’s Whiskey’ (2010)



As the years pass, Kenny Chesney’s duet with Grace Potter could move up to the No. 2 spot on this list, but it’s too new to judge how it will hold up over time. Chesney found a brilliant piece of songwriting and the perfect duet partner to recreate this heartbreaker, currently the No. 3 song on the Top 10 Kenny Chesney Songs list. It’s one of only three platinum records he has under his belt, and it also earned him a long line of award nominations in 2011 and early 2012.



‘There Goes My Life’

From ‘When the Sun Goes Down’ (2004)



This song spent seven weeks on top of the country music charts and reached No. 29 on the all-genre charts. Like “The Good Stuff,” it’s a simple, easy-to-follow story that tugs at one’s heartstrings with all of its weight. Song No. 2 on the Top 10 Kenny Chesney Songs list is a tear-jerker — there’s no doubt about it. We give him high points for sales, chart position, lyrical content and live reaction on this one. In fact, there’s only one song that topped “There Goes My Life” …




From ‘The Road and the Radio’ (2005)



“Summertime” is arguably the best summer country song of all time. Recently, it landed at No. 29 on the Taste of Country list of the Top 100 Country Songs, which allowed only one song per artist. “Summertime” went platinum, while also dominating the Billboard charts in 2006. It’s the only song on the Top 10 Kenny Chesney Songs list to come from his The Road and the Radio album. More than any other song the singer has ever recorded, “Summertime” has stood the test of time. It sounds like one he could have cut today, not over a half decade ago.


Next: Kenny Chesney Through the Years

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