My Toby Keith Deep Dive Disaster
Okay guys, so this week I got obsessed. Like, really obsessed. For no dang reason, Toby Keith’s old song “Should’ve Been a Cowboy” popped into my head while I was cleaning the grill. Boom. Suddenly, I needed to remember all his best hits.

Figured I’d google “best Toby Keith songs” real quick before dinner, right? Wrong. Every single list I clicked on felt… off. Either too short, missing stuff I knew was huge, or including weird deep cuts I never heard of. And the order? Made no sense. Left me more annoyed than informed.
That’s when my stubbornness kicked in big time. Decided, screw it, I’ma make my own dang Top 10 list. The real must-hears, based on what actually ruled the radio and my own dusty CDs. But first, gotta remember ’em all. My memory ain’t what it used to be.
Dug around my music stuff – mostly streaming now, but I found a couple old compilation CDs and a USB drive labeled “Country Stuff.” Got everything into one big chaotic Spotify playlist. Started just playing it all, chronologically. Man, some songs… the memories flooded back!
- How Do You Like Me Now?! blasting during senior year… yeah, felt rebellious.
 - Courtesy of the Red, White and Blue EVERYWHERE after 9/11… still powerful.
 - That Beer for My Horses duet with Willie… pure bar jukebox magic.
 
But man, trying to rank ’em? Pure torture. Spent hours listening, skipping, replaying. Arguments with myself: Is “I Love This Bar” really top tier, or just super fun? Does “As Good As I Once Was” belong in the top? This was way harder than I thought!
Finally, just had to call it. Picked ten that felt essential – the ones everyone knew, the ones that defined his sound and attitude. Created a new playlist called “Toby’s Big Guns.” My rough list:

- “Should’ve Been a Cowboy”
 - “How Do You Like Me Now?!”
 - “Courtesy of the Red, White and Blue (The Angry American)”
 - “Beer for My Horses” (with Willie Nelson)
 - “I Love This Bar”
 - “As Good As I Once Was”
 - “American Soldier”
 - “Whiskey Girl”
 - “God Love Her”
 - “Made in America”
 
You agree? Probably not! Could argue swaps all day – maybe “Get Drunk and Be Somebody”? Maybe “You Shouldn’t Kiss Me Like This”? That’s why these lists drive you nuts. But honestly, forcing myself to listen through it all again was worth the headache. Forgot how many jams he truly had. Blasted my playlist while finishing up that grill cleaning – way better than any algorithm playlist I’d found.
