Montgomery Gentry's 10 Best Songs: Critic's Picks

Eddie Montgomery and Troy Gentry of Montgomery Gentry
Stephen J. Cohen/Getty Images

Eddie Montgomery and Troy Gentry of Montgomery Gentry performs during the Kentucky Cares Tornado Relief benefit concert at Busters Billiards & Backroom on May 9, 2012 in Lexington, Kentucky.  

The shocking news of the death of Montgomery Gentry co-founder Troy Gentry Friday (Sept. 8) brings to a close the career of one of the biggest country duos of the past two decades. The guys could wring pure emotion by weaving a lyric about the simple pleasures of home and a good woman, yet they could also turn up the tempo with a lively rocker designed to make the fan tap their toes or nod in agreement.

Here are ten great moments that will continue to live on in the hearts of “T-Roy” and Eddie -- forever. Each track serves as a reminder of just how special that talent blend was. Our thoughts and prayers are sent ot Gentry’s family at this time.

10. Montgomery Gentry - "She Don’t Tell Me To"

The lone single from their 2005 compilation CD Something To Be Proud Of, this tender Montgomery Gentry love song details a man who takes pride in doing the little things to express his feelings for his significant other -- but not out of obligation, simply because it’s the emotion that he feels. To promote the song, Troy and Eddie traveled north to Iceland to film the video for the song.

9. Montgomery Gentry -- "Roll With Me"

Gentry sang lead on this effective number, which reached the pinnacle of the Country Songs chart during Christmas week of 2008. The record featured a guest vocal appearance from Five For Fighting. The duo invoked plenty of wisdom in the lyrics, all about learning their lessons from the life the subject of the song has lived.

8. Montgomery Gentry -- "Hillbilly Shoes"

Neither Troy Gentry nor Eddie Montgomery had any idea what was about to happen in their careers when their debut single hit the airwaves in the late winter of 1999. This lively song -- about paying tribute to one’s roots notched their first hit on the charts, peaking at No. 13 that year, kicking off a career that definitely stood the test of time.

7. Montgomery Gentry -- "Where I Come From"

Ace songwriters Rodney Clawson and Dallas Davidson penned the song that would become the duo’s final major hit, about a man who was proud of his southern heritage. The track was from their Average Joe’s release Rebels On The Run, and also their second Gold-selling single.

6. Montgomery Gentry -- "My Town" 

In a sense, this 2002 single mined a lot of the same musical and lyrical ground as Song #7, as the singer is showing a visitor around the area that they grew up -- and what makes it so special. Even so, there was a charm about this song, which took pride in everything in a community from the water tower to Sunday morning worship services to the local diner. The song served as the title track from their third studio album.

5. Montgomery Gentry -- "Back When I Knew It All"

You’re never as smart as you are when you are in your younger years -- or so we all think. This 2009 masterpiece rings with plenty of truth about a man who realizes just how much he didn’t know when he was starting out on his own. Both members took their turn on the song, which became their fourth chart-topper.

4. Montgomery Gentry -- "Gone"

Perhaps the hardest-rocking song in the Montgomery Gentry song catalog, Gentry summoned quite a bit of swagger on this track about a man lamenting the fact that his lover has left him. While the song actually sounds too upbeat at times to be a song of heartbreak, the duo made this one simmer through the verses -- and turned everything up in the chorus.

3. Montgomery Gentry -- "Hell Yeah"

There was definitely a feeling of nostalgia with this 2003 single from My Town -- which featured a man and a woman looking back on their lives in a bar. The man came from the “Haggard Generation,” and had lived his life in a true old-school fashion, while the woman in the song came of age during the “Me Generation.” Both wanted to escape the pressure of life in the present day, and go back to a time period where “love was easy.” Funny, that’s how we feel today.

2. Montgomery Gentry -- "Something To Be Proud Of"

One of the more meaningful compositions that the group cut during their two-decade run together, this emotional song documented the fact that a son had made his father proud by simply doing the best that he could have done with what he had at the time. As it turned out, it was the simple things - like taking care of one’s family -- and serving your country -- that was the true mark of a man.

1. Montgomery Gentry -- "Some People Change"

This powerful Montgomery Gentry song was unusual in that the band was actually not the first -- or the second -- to record it. The song was originally cut by Kenny Chesney in 2004, and then again the next year by Nashville Star contestant George Canyon. But, the third time was the charm -- and it ended up making an unlikely fan of the duo. As it turned out, Maya Angelou was a huge fan of this song, and invited the duo to perform the song at an event she was a part of at the Tennessee Performing Arts Center in 2007 with the Fisk Jubilee Singers. The poet (just like the rest of America) was drawn to this song about a man coming to terms with his past, and the social evolution that the singer of the song, has underwent over the years. Whether it be addiction or racism, it was possible to turn a new page and start completely anew, a message that resonated with the legendary poet -- and millions of others!