A Look Back At Toby Keith’s 5 Most Underrated Heartbreak Ballads

Toby Keith Country Music
Toby Keith

It’s been a tough few years for 90’s country legend Toby Keith.

After announcing his cancer diagnosis and taking some time away from public performances to undergo treatment, things have been seemingly on the upswing for the Big Dog Daddy.

He shared an update with fans at the People’s Choice Country Awards back in September before a laying down a powerful performance of “Don’t Let The Old Man In”:

“I’ve walked some dark hallways. The Almighty’s riding shotgun. But I feel pretty good. You have good days and bad days, but it’s a little bit of a rollercoaster. But I’m doing a lot better than I was this time last year.

I’ve always wrote with a prayer, and as long as I have Him with me, I’m cool. You just have to dig in, you don’t have a choice.”

He admits that you’re never really out of the woods when battling cancer, but it’s been awesome to see Toby back in action and in honor of that, I think we should take a trip down memory lane and look back at some of his best work.

While the rowdy, patriotic, boot-in-your-ass songs that Toby is best known for are great (I’ve had many a night belting out “Made in America” Bud Heavy in hand), when I first heard “She Never Cried in Front of Me,” I was absolutely floored.

Growing up on my dad’s 80’s music, I was accustomed to synth-rock ballads, but the combination of Toby’s big voice, country instrumentation, and right-to-the-heart lyrics opened my eyes to a whole new style of music.

Here’s five of his best (and most underrated) country heartbreakers.

5. “Cryin’ For Me (Wayman’s Song)”

Written as a tribute to his late friend Wayman Tisdale, “Cryin’ For Me” is a certified tearjerker, one that caught fans off guard when it followed up “American Ride.”

4. “Does That Blue Moon Ever Shine On You”

A classic for loyal Toby fans and easily deserving of a spot on this list. Plus, check out the head of lettuce on that man. With the fading video cuts and white cowboy hat, this might be a top music video as well.

3. “Who’s That Man”

Losing the wife, the kids, the house, the dog… Toby does a great job carrying on this country music tradition.

2. “Wish I Didn’t Know Now”

Toby’s 1994 hit single “Wish I Didn’t Know Now” tells heartbreaking story of a guy finding out that his lover is cheating on him, and rather than knowing the truth and breaking up, he’d just prefer to continue on not knowing. Ignorance is bliss, right?

1. “She Never Cried In Front Of Me”

Easily the best Toby Keith song, in my humble opinion, and the best example of a real country ballad. Grab the tissues, these one cuts deep.

A beer bottle on a dock



A beer bottle on a dock