10 Essential Kenny Chesney Songs

Kenny Chesney is one of Country music’s foremost entertainers. Since his chart debut in 1993, Chesney has steadily built one of the most spectacular careers in the genre. Racking in eight Entertainer of the Year trophies and spending a whopping 76 weeks at No.1,  it’s safe to say that Chesney has more than left his mark on the genre…and he’s not finished yet!

We took a look back through the Tennessee native’s impressive catalog and selected ten of his most iconic hits. Did your favorite tracks make the cut?

(Arranged chronologically)

“She’s Got It All” – from I Will Stand
Chesney first hit the top-10 in 1995 with “Fall In Love,” but it was this rollicking celebration of a significant other that paved his way to the top for the very first time. The song was written by Drew Womack, at the time a member of The Sons of the Desert, and the first Chesney hit for Craig Wiseman.

“She Thinks My Tractor’s Sexy” – from Everywhere We Go
It’s rare to include a single on these lists that wasn’t a top-10 hit, but this down-home celebration of farm machinery helped to put Chesney on the A-List. Some questioned the choice of the singer to record the song, but Paul Overstreet, writer of such hits as “On The Other Hand” and “Forever and Ever, Amen,” didn’t have any problem with the light-hearted lyrics. After all, he penned the song with Jim Collins.

“The Good Stuff” – from No Shoes, No Shirt, No Problems
Craig Wiseman struck again with a song that surprised many with its’ sense of depth and passion about the things that are truly important in life. Collins – another Chesney favorite – also had a hand in writing this song, which gave Kenny one of two of his biggest hits on the Billboard charts, topping the list for seven weeks!

“No Shoes, No Shirt, No Problems” – from No Shoes, No Shirt, No Problems
Chesney had sung about the beach before, primarly in 1999’s “How Forever Feels.” He took it a step further with this fun composition from Casey Beathard. It spent five weeks in the runner-up position on the charts, but helped to establish the singer’s identity as man perfectly at home on the water.

“There Goes My Life” – from When the Sun Goes Down
A true sign of a great song is if you can remember where you were when you first heard it. I was in the parking lot of The Music Mill when I heard this powerful song about how a child – no matter if planned or not – can totally transform a life. The last verse of this song still moves me fourteen years later. Credit Neil Thrasher and Wendell Mobley for a great composition, and Chesney for delivering what still stands as one of his most effective performances.

“Who You’d Be Today” – from The Road and the Radio
Aimee Mayo and Bill Luther hit all the right emotional spots with this emotional tribute to a special someone in a life that had passed away. As painful as the song might be to the listener, even greater is the sense of hope that one gleams from the lyric about being reunited….one day.

“Living In Fast Forward” – from The Road and the Radio
Rivers Rutherford and 1990s hitmaker David Lee Murphy contributed to this driving number about a man who is rolling through life at too quick of a speed, even though deep down he knows there’s nothing he’d rather be doing. Chesney particularly cooks on this one live!

“Don’t Blink” – from Just Who I Am: Poets & Pirates
Though Chesney has scored with many up-tempo party numbers, he also knows his way around a ballad. This one is evidence of a man who knows how to pick a great lyric. Casey Beathard and Chris Wallin are responsible for this one about how quickly life can go by, with the morale of the story being to always cherish the good times.

“The Boys Of Fall” – from Hemingway’s Whiskey
Written by: Casey Beathard, Dave Turnbull
The first single off of Hemingway’s Whiskey, this one was a little bit of a departure for the singer, though writers Casey Beathard and Dave Turnbull knew better. Chesney is a longtime football fan, whether he’s rooting for the Tennessee Vols or the New England Patriots. Anyone who ever played the game – or stood in the cheering section – felt the lyrics of this one, which remains one of the more underrated gems in his catalog.

“You And Tequila” (duet with Grace Potter) – from Hemingway’s Whiskey
Matraca Berg and Deana Carter scored a huge hit when Chesney included this introspective ballad on Hemingway’s Whiskey. The inclusion of Grace Potter was nothing but a stroke of genius, as Kenny hit with a song that is sure to be a perfect slow-down moment in his shows for years to come!

Stream our Kenny Chesney playlist below and click HERE to subscribe.