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The 10 Best Toby Keith Songs, Ranked

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It’s easy to assume that a lot of folks expect the worst from Toby Keith songs. Before “bro-country” became a thing, most thought of Keith’s post-9/11 output as the epitome of lowbrow country songs.

Even if he didn’t come across as the most eloquent patriot then with “The Taliban Song,” “American Ride” and others, it’s unfair to dismiss Keith as a bad guy or skip over any album in his discography. Respectively, those songs are on the same albums as the underappreciated “Baddest Boots” and “Gypsy Driftin’.” Even beyond his more political material, if you don’t care for the macho bravado of “How Do You Like Me Now?!,” skip ahead to the gorgeous, more traditional-sounding “New Orleans.”

From his early ’90s output, known mostly for debut single Should’ve Been a Cowboy,” to present day, Keith has consistently cranked out quality singles. In between, he’s done it all– dueting with Sting, hanging out with Wayman Tisdale and cutting the fun holiday album Christmas to Christmas (featuring the amazing song titles “Hot Rod Sleigh,” Bethlehem in Birmingham” and “Jesus Gets Jealous of Santa Claus”).

10. “American Soldier”

Instead of falling back on political sloganeering, Keith celebrates the common men and women doing uncommon things for their country.

9. “Does That Blue Moon Ever Shine On You?”

Sustained greatness in ’90s Nashville pretty much required not just energetic songs worthy of a stage show, but also tender love ballads like this, “Victoria’s Secret,” “Upstairs Downtown” and others that sounded ready-made for the airwaves.

8. “She Ran Away With a Rodeo Clown”

Keith always does great with songs about the rodeo, be it the serious “Rodeo Moon” or this light-hearted deep cut from 1997. It’s from the same “hat act” phase that brought us “Dream Walkin” and “Double Wide Paradise.”

7. “Jacky Don Tucker (Play By The Rules Miss All the Fun)”

How this one didn’t create a beloved outlaw character is beyond us. It’s fast, furious and fun, from back when that formula worked so well for John Michael Montgomery and others.

6. “A Little Too Late”

The influence of old Mexico, a place that long inspired Marty Robbins and numerous other greats, adds a touch of class to this co-write with Dean Dillon and frequent Keith collaborator Scotty Emerick.

Read More: Toby Keith and Blake Shelton Perform ‘Should’ve Been a Cowboy’ at 2018 ACM Awards

5. “Red Solo Cup”

If someone like Jerry Jeff Walker had gotten to this loose, funny barroom sing-along off the Clancy’s Tavern album first, we’d all sing its praises louder.

4. “I Love This Bar”

This song tells of all sorts of characters you’d find in most any small town, bound by geography and a desire to drink beer and Jack Daniels out of Mason jars.

3. “Beer For My Horses” (With Willie Nelson)

When this song came out, the widespread appeal of Willie Nelson forced even the sternest Keith skeptic to share a good laugh with these two close friends.

2. “Should’ve Been a Cowboy”

The song that started it all was this classic ’90s country single that’s normally brought up first when explaining why Keith is way better than some want to admit.

1. “Who’s That Man”

Although it’s less celebrated now than “Should’ve Been a Cowboy,” this gorgeously written and sung composition epitomizes all of the good qualities of Toby Keith, a country music superstar with a tender heart to go along with his rough exterior.

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The 10 Best Toby Keith Songs, Ranked