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The 10 Best John Michael Montgomery Songs, Ranked

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John Michael Montgomery songs represent pretty much every mainstream country music trend from the ’90s. Starting with his 1992 debut album, he added to the musical discourse on line dancing, hat acts, surprisingly decent holiday songs about Santa and Rudolph, traditionally-grounded storytelling and pop crossovers.

A native of Danville, Kentucky, Montgomery inherited the same same heaven sent helping of talent as older brother Eddie Montgomery of Montgomery Gentry fame. Like Eddie, he’s capable of the fiery showmanship Nashville always craves, yet he knows how to put his sensitive side to use. In fact, it’s not the younger Montgomery brother’s ability to sling a guitar and sing Alan Jackson-style honky tonk that led to many of his best songs. Instead, it’s the sentimental country songs, grounded in a real love for faith, family and country, that shook up the country charts then and now best define a varied career.

Check out these 10 songs, plucked from the John Michael Montgomery discography, for a sampling of a tremendous talent who’d make you cry one with one song and then, a couple of tracks later, have you up on your feet dancing a jig.

10. “I Swear”

This one and “I Can Love You Like That” are decade-specific stereotypes at this juncture, but at least they’ve aged gracefully. It’s a reminder that Montgomery’s voice did wonders with sentimental material (see also “Line on Love,” “Little Cowboys Cry” and “Nickels and Dimes and Love”).

9. “Country Thang”

I used to think Charlie Daniels sang this one, based on both vocal delivery and lyrical content. That’s a high complement, considering that not everyone gets confused for a Hall of Famer.

8. “Mad Cowboy Disease”

This might be the best Toby Keith song that never was. It’s a funny yet seriously rocking story about a drunken night on the town. Other examples of clever wordplay in Montgomery’s catalog include the always fun “Paint the Town Redneck.”

7. “Full Time Love”

Once again, Montgomery is all things to all ’90s nostalgia hounds. He’s even got some well-aged songs in the “hat act” mold, including this cut from 1994, plus “If You’ve Got Love” and other tracks worth revisiting.

6. “Weekend Superstar”

When current country singers get it right, it’s often through saluting the common working people in the audience. Here, Montgomery celebrates the guy who’s working for the weekend.

5. “Rope the Moon”

With this love song to fatherhood, Montgomery whips up an analogy to real-life cowboys. It’s a gentle ballad in line with some of George Strait’s later hits.

4. “Cowboy Love”

Back when good singers like Joe Diffie and Ronnie Dunn flaunted their talents with boot-scooting dance numbers, Montgomery joined in on the fun.

3. “Sold (The Grundy County Auction Incident)”

Montgomery joined Leroy Van Dyke as one of the great singers of country songs about auctioneers with one of the most memorable hits of its time, along with the equally infectious “Be My Baby Tonight.”

2. “Letters From Home”

Another great lesson contemporary artists learned from their 20th century predecessors is how to celebrate the brave men and women in our Armed Forces with a touching song.

1. “The Little Girl” (feat. Alison Krauss and Dan Tyminski)

The power and message of this song could be an essay unto itself. With the help of Krauss, Montgomery sang what has to be one of the best statements of unwavering faith in the face of tragedy in modern country or gospel music.

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The 10 Best John Michael Montgomery Songs, Ranked