Kenny Chesney Turns 53: Outsider’s 5.3 Favorite Songs to Celebrate His Birthday

by Jim Casey

In honor of Kenny Chesney’s 53rd birthday on March 26, we’re celebrating with Outsider‘s 5.3 Favorite Songs by the East Tennessee tunesmith.

With 31 No. 1 hits on the Billboard Country Airplay chart (most all-time)—and more than 20 additional Top 10s—selecting 5.3 songs from Kenny’s catalog is an arduous undertaking. Also, you may be asking what’s .3 of a song? Don’t worry, we enlisted the help of Outsider editor Jim Casey and writers Matthew Wilson and Clayton Edwards for this Herculean Herchesnian undertaking.

1. ‘Tin Man’

‘Tin Man’ didn’t exactly set the charts ablaze (No. 70) when Kenny released it as the second single from his 1994 debut album, In My Wildest Dreams. But Kenny Chesney wasn’t content to let his brokenhearted ballad linger in obscurity. When Kenny dropped his Greatest Hits album in 2000, he re-recorded the song and released it as a single. Now, some will claim The Wizard of Oz reference is about as fresh as a rusty nail, but we like the heartbreaking (or lack there of) metaphor of the Top 20 tune. — JC

Kenny Chesney produced a bona fide tear-jerker with this 2007 tune that feels like it came out yesterday. Sometimes life goes by a little too fast for people’s liking. “Don’t Blink” is a little musical carpe diem, urging listeners to seize the time that they have on this earth. Leave it to Chesney to produce something that’s both joyous and wholesomely tender at the same time. With this song, Kenny provided the soundtrack for countless high school reunions and wedding anniversaries. —MW

3. ‘That’s Why I’m Here’

“That’s Why I’m Here” was the third single from Kenny’s 1997 album, I Will Stand. Once again, Kenny Chesney tugs at the ol’ heartstrings in this Top 5 tune. The song takes us into the mind of an alcoholic who hits rock bottom, but resolves to push toward recovery. It hits hard when he tells his significant other that he knows it’s probably too late for them to reconcile. However, he just wants her to be “there” when he makes his “stand” in recovery. If the rest of the song didn’t get you, that final chorus is guaranteed to drill you right in the heart. —CE

4. ‘Back Where I Come From’

Kenny channels some hometown nostalgia in this up-tempo country anthem for the ages. The Tennessee native may be singing about his hometown of Knoxville, but it’s easy to imagine him talking about any small town. Featured on his 1996 album, Me and You, the Mac McAnally-penned tune has become a fan-favorite. With his booming vocals, Kenny Chesney proves reflecting on the past doesn’t have to be a gloomy affair. Instead, crank up that volume and celebrate back where you came from. —MW

5. ‘She Thinks My Tractor’s Sexy’

Not every country song has to be an emotional roller-coaster. Have some fun. Get on a tractor. That’s what Kenny Chesney did with his lively single, “She Thinks My Tractor’s Sexy,” which was featured on his 1999 album, Everywhere We Go. While the tune peaked at No. 11, it’s the one everybody remembers. It’s fun, goofy, and a great look at where the future leader of the No Shoes Nation was heading. More importantly, this is just one of those songs that will put a smile on your face every time you hear it. That’s hard to beat. —CE

.3. ‘Hey, Good Lookin”

Yes, we know there’s no such thing as .3 of a song. Stop taking everything so literally. In fact, Kenny’s contribution to Jimmy Buffett’s “Hey Good Lookin'” is more like .2, since it also featured Clint Black, Alan Jackson, Toby Keith, and George Strait. Whatever, we’re not mathematicians. But when this team of A-listers put their pipes on the Hank Williams classic in 2004, it became a Top 10 hit. We recognize Jimmy Buffett has a license to chill—and with Clint, Alan, Toby, George, and Kenny backing him up, there’s really no debate about it. —JC