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The 10 Best Montgomery Gentry Songs, Ranked

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Eddie Montgomery and Troy Gentry found magic in the late 1990s when they founded country music duo Montgomery Gentry. Over the next 18 or so years, they carved out their unique place in the scene that nobody duplicated.

For nearly two decades, Montgomery Gentry owned their brand of unabashed country rock, with equal parts party and southern etiquette. They both hailed from Kentucky before moving to Nashville, Tennessee, which helps explain some of their rock ‘n roll tendencies. The “Bluegrass State” is also well known for a respectable southern rock scene.

They gained plenty of love early on, winning Vocal Duo of the Year and unseating Brooks & Dunn for the first time in eight years at the 2000 CMA Awards. They even helped Charlie Daniels earn his first Top 40 single in a decade when Daniels sang on their single “All Night Long.”

Montgomery Gentry released six albums on first record label Columbia records before making a switch to Average Joes Entertainment. Though Montgomery Gentry didn’t see a whole lot of radio love or appear much on the country songs chart in the later part of their career, their records and shows kept selling thanks to a loyal fanbase they built up over the years.

On Sept. 8, 2017, Troy Gentry passed away in a tragic helicopter crash in Medford, New Jersey. After a few months of uncertainty, Montgomery confirmed that he would continue the group without his longtime partner, which has a studio album finished and ready for 2018. In honor of the band, let’s take a look at the 10 best Montgomery Gentry songs.

10. “Where I Come From”

Country music has plenty of small town America anthems, but most don’t come close to what Montgomery Gentry came out with. “Where I Come From” may not be Shakespeare by normal standards, but its one of the best unapologetically red blooded, chest-beating tiny town love tunes of the past 20 years.

9. “Tattoos & Scars”

The title track off their debut record, “Tattoos & Scars” is the type of song that made Baby Boomers fall in love with the group. It features a cocky youngster showing off his tattoos and a wiser old-timer showing his natural scars and explaining the difference.

8. “One In Every Crowd”

One thing Montgomery Gentry does really well is sing songs that make their fans say, “That’s about me!” Their track “One In Every Crowd” is a perfect example of that.

7. “Speed”

A Top 5 single from 2002, “Speed” is a great twist on the cliché truck song. In it, the protagonist trades in his truck for a fast car to try and outrun the memory of an ex-girlfriend. It’s simple but executed brilliantly.

6. “Hell Yeah”

The stadium-ready “Hell Yeah” is an unmistakable song that seems to grace the radio in particular during Spring Break season.

5. “Better Me”

Montgomery debuted new song “Better Me” at the Grand Ole Opry House after Gentry’s memorial service, but the song doesn’t just make the list because of how emotional it is. It’s a really well-written tune with a tender sentiment that the band doesn’t show all that often. Expect their new album to land on the country charts again thanks to songs like this one.

4. “Lucky Man”

Speaking of sentimental, this stellar song earned the duo its only Grammy nomination in 2008.

3. “If You Ever Stop Loving Me”

The duo’s first No. 1 single on country radio, “If You Ever Stop Loving Me” from 2004 remains a fan favorite. The carefree tune gets stuck in your head for days.

2. “My Town”

Probably the only small town anthem that tops “Where I Come From,” “My Town” is kind of the original version of their tiny town pride tune back from 2002.

1. “Something To Be Proud Of”

“Something To Be Proud Of” is a No. 1 single from 2005 that perfectly encapsulates what Montgomery Gentry is all about. A lot of pride, some elderly wisdom, a little rowdiness and plenty of country sensibility.

WATCH: Remembering the Life and Music of Troy Gentry

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The 10 Best Montgomery Gentry Songs, Ranked