4 Kenny Chesney Songs From the 90s That Should Have Been Big Hits

Kenny Chesney has talent, but he also has tenacity. Very little about Chesney’s start in country music indicated the superstar career he would one day have, including becoming a member of the Country Music Hall of Fame.

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Chesney’s first single came out in 1993. It took him four years and ten singles before he had a No. 1 hit, with “She’s Got It All”, out in 1997. We found four singles Chesney released in the 90s that should have been hits, even if they may have been before his time.

“Grandpa Told Me So”

Kenny Chesney released “Grandpa Told Me So” in 1995, from All I’ve Ever Known, his first album on a major record label. Mark Alan Springer and James Dean Hicks penned the song, which peaked in the Top 25.

The song begins with, “If you don’t get in the water, you’re never gonna learn to swim / He said a snake is just as scared of you, as you are of him / He could tell by the moon when the fish would bite / Seems there was nothing that he didn’t know / And as a kid I believed, ’cause grandpa told me so.” It’s a sweet story song that likely would have been a big hit for Chesney if he had released it later in his career.

“I Will Stand”

“I Will Stand” is a romantic tune written by Mark Germino and Casey Beathard, and the title track of Chesney’s fourth studio album. The song says in part, “I will not be the one / Who turns his back and runs / When things get rocky down the line / And I will not be the one / Holdin’ the smokin’ gun / If our love don’t stand the test of time.”

“I Will Stand” peaked in the Top 30, which is not bad, but not nearly the success he might have had with the song later in his career.

“Back In My Arms Again”

“Back In My Arms Again” is an uptempo track, out in 1996, on Kenny Chesney’s third studio album, Me and You.

The song says in part, “Well I’m getting to know this old town like never before / Walking every street, knocking on every door / Girl, wherever you are, I want you back / I love you baby, and I’m sure about that / Whatever it takes, there’s nothing that I won’t do / Till you’re back in my arms, back in my arms again.”

Hit songwriters Cris Moore, Lee Roy Parnell, and Rory Bourke penned the song, which didn’t even crack the Top 40.

“The Tin Man”

“The Tin Man” actually became a hit for Chesney, just not when he first released it in 1994. The song, written by Chesney, along with Stacey Slate and David Lowe, did not even chart when it first came out.

It’s lack of success is especially surprising since the lyric says, “It’s times like these / I wish I were a tin man / You could hurt me all you wanted / And I’d never even know / I’d give anything just to be the tin man / And I wouldn’t have a heart and I wouldn’t need a soul.”

“That was the first song I wrote shorter than five or six minutes,” Chesney tells The Tennessean. “The song leads everything. That was burned into my psyche early on when I first moved to Nashville.”

Chesney released the song again in 2001, and that version became a much bigger hit for him.

Photo by Beth Gwinn/Redferns