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Top 10 Kenny Chesney Songs

Not only is it difficult to decipher the top Kenny Chesney songs, it's impossible to even list all of his No. 1 singles on this list. One of the defining American country singers of the past two decades, Chesney has more than 30 Top 10 hits, 11 certified gold records and four consecutive Entertainer of the Year Awards. Here are our favorites, which reminisce on first love, the importance of family and the simple things in life.
10
'I Lost It'
'I Lost It' was one of two new songs released as a single on Chesney's 2000 'Greatest Hits' album. Co-written by Neil Thrasher and Jimmy Olander, the track also features uncredited background vocals from singer-songwriter Pam Tillis.
09
'No Shoes, No Shirt, No Problems'
Run down by work, the song's protagonist dreams of a tropical getaway where he can "soak up life for a while in laid-back mode" and there's "no boss, no polite, no stress, no dress code." The title track is off Chesney's seventh studio album -- which produced five Top 10 charting singles and went platinum four times in the US.
08
'Don't Happen Twice'
The second new single from 2000's 'Greatest Hits' album to top the country charts, 'Don't Happen Twice' refers to a first love, reminiscing on sweet memories where "we sang 'Bobby McGee' on the hood of my car" and "made a wish on every star in that clear September sky."
Kenny Chesney Dont Happen Twice
07
'How Forever Feels'
Chesney has "been around the block a time or two" but humbly admits, in this single, that he's ready to spend the rest of his life with one woman. Off 'Everywhere We Go,' his fifth studio album, 'How Forever Feels' teamed up with 'You Had Me From Hello' (listed at No. 6) to produce his first two back-to-back No. 1 hits.
Kenny Chesney How Forever Feels
06
'You Had Me From Hello'
Kenny Chesney songs are no stranger to talking about first romances, especially love at first sight, such as in this ballad -- inspired by the famous 'Jerry Maguire' line. Chesney ironically ended up marrying actress Rene Zellweger -- who spoke those famous words -- only to annul the marriage four months later.
05
'There Goes My Life'
This heartwarming story follows the life of a high school football player who finds out his girlfriend is pregnant, ruining his dreams of moving out West. But in a twist of fate, his initial, doomed words of "there goes my life" later refer to watching his loved daughter, all grown up, go off to college.
Kenny Chesney There Goes My Life
04
'Anything but Mine'
Keeping with the teenage first-love theme, 'Anything but Mine' recalls a summer vacation romance that inevitably ends. It was the fifth single from Chesney's 2004 album, 'When the Sun Goes Down.'
03
'Don't Blink'
"Don't blink," urges an aged man who tells a youngster to appreciate every moment in life, from being a child, to raising kids and even spending the last years with your spouse. The song -- off Chesney's 12th studio album, 'Just Who I Am: Poets & Pirates' -- is currently tied with 'Never Wanted Nothing More' for the fastest-rising single of his career.
02
'I Go Back'
Kenny Chesney's song 'I Go Back' ties popular hits 'Jack & Diane,' 'Only the Good Die Young' and 'Rock'n Me' to his fond memories in the past. But apparently a tune about living in the moment proved to be slightly more popular on the country charts, as it failed to overtake Tim McGraw's 'Live Like You Were Dying.'
01
'The Good Stuff'
Not only is 'The Good Stuff' our top Kenny Chesney song, it's his most successful. The fifth No. 1 single of his career spent seven weeks at the top of the country charts, becoming the top country single of 2002 and winning CMT and ACM accolades.

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