Toby Keith’s Heartbreak Ballads Are Incredibly Underrated

Country Music

Can we get a petition going to bring pack some Toby Keith heartbreak anthems? I mean, what do we gotta do to get this kind of stuff back on the radio?

While the rowdy, patriotic, boot-in-your-ass songs that Toby is best known for are great (I’ve had many a night singing “Made in America” at karaoke, 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 ’80s 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.

When you think of Toby Keith, you generally think of his rowdy party songs and his American pride, but I’m here to tell you that his tear-in-your-beer ballads are the best songs of his long and successful career.

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

6. “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.”

5. “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. Throw in the fading video cuts and white cowboy hat and this might be a top music video as well.

4. “Who’s That Man”

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

3. “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?

2. “You Shouldn’t Kiss Me Like This”

That moment right between “just friends” and “we’re together.” The limbo, the questions, the wanting, all wrapped up into one song.
Also, the music video gives off some strong Garth Brooks “That Summer” vibes…

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.

Bonus: “Upstairs Downtown”

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