While He May Be Remembered For His Patriotic Anthems, Toby Keith’s Heartbreak Ballads Were Where He Really Shined

Toby Keith
Toby Keith

Hard to believe we’ve lost Toby Keith.

His family announced today that the larger-than-life cowboy from Oklahoma passed away yesterday after a 2-year battle with stomach cancer.

Already, tributes have been pouring in from the country music world and beyond, with many remembering Toby’s vast catalog of hits that earned him 20 #1 songs over his legendary career.

Of course the first songs that come to mind when many think of Toby Keith (aside from “Should’ve Been A Cowboy”) are his patriotic anthems. Songs like “Courtesy of the Red, White and Blue,” “American Soldier” and “Made in America,” released in the years following the 9/11 terrorist attacks, cemented Toby’s spot as the face of the patriotic country movement.

And who still doesn’t get fired up when you hear him sing “we’ll put a boot in your ass it’s the American way?”

But Toby was so much more than a singer of patriotic country songs.

In fact, it was on his heartbreak ballads where he shined the most.

This was evident from the very beginning of Toby’s career, when he followed up his 1993 debut single “Should’ve Been a Cowboy” with “He Ain’t Worth Missing” – which, like many of his hits, Toby wrote completely on his own:

“Oh, he ain’t worth missing
Oh, we should be kissing
Stop all this foolish wishing
He ain’t worth missing
I know your head is turning
I know your heart is burning
Girl, you gotta listen
Don’t you know he ain’t worth missing”

Then in 1994 Toby dropped what may be my favorite song from his entire catalog with the heartbreaking “Wish I Didn’t Know Now,” a tearjerker of a ballad about a man who would rather not know that his partner was unfaithful than have to deal with the pain of missing her.

And over the course of his 3-decade career, Toby continued to mix these incredible ballads in with hits like “How Do You Like Me Now?” and “Red Solo Cup.”

It’s impossible to list all of the incredible ballads in Toby’s catalog, from “Who’s That Man,” a song about seeing your ex-wife happy with her new family, to “Does That Blue Moon Ever Shine On You,” which tells the story of a man who wonders if the love he lost still thinks about him the way he misses her.

“Does that blue moonEver shine on you?I want to hold you close to meAnd feel just like it used to be andBaby, if you feel like I doYou can come to meDoes that blue moonEver shine on you?”

And of course who can forget another solo write from Toby with “You Shouldn’t Kiss Me Like This?”

And even after 9/11 when Toby’s music took a noticeably patriotic turn, he continued cranking out the incredible heartbreakers – even if they didn’t get the attention that his more pro-America anthems were getting.

Songs like “Big Blue Note,” “She Never Cried In Front Of Me,” and the incredible “Cryin’ For Me (Wayman’s Song)” proved that Toby never lost his versatility – or his talent for writing ballads. And they also showed the foolishness of trying to paint him as an artist solely interested in capitalizing on the feelings that dominated our country post-9/11.

Of course most recently, Toby was widely praised after his 2019 song “Don’t Let The Old Man In” got new life when he performed the song on the People’s Choice Country Awards in the midst of his cancer battle, a poignant moment that reminded everybody of the talent and versatility that Toby’s shown throughout his career.

So I’m sure there will be a lot of people cranking up “Courtesy of the Red, White and Blue” or “Should’ve Been a Cowboy” today. But when you dig a little deeper into his catalog, that’s when you’ll realize how truly brilliant Toby Keith was as an artist and a songwriter.

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