When Montgomery Gentry, the duo made up of Eddie Montgomery and Troy Gentry, released their first album, Tattoos & Scars, in 1999, very little was known about the two men other than they were both from Kentucky and that Montgomery was the younger brother of '90s superstar John Michael Montgomery.

But over the next two decades, Montgomery Gentry became one of the most successful acts in country music, selling millions of albums, charting more than 25 songs and ending Brooks & Dunn's eight-year run as the reigning CMA Awards Vocal Duo of the Year in 2000. Although Montgomery suffered an incredible loss when Gentry died in a helicopter crash in September of 2017, he's continuing to tour and share new music -- what Gentry would have wanted, he says.

While Montgomery Gentry have far too many hits to list, The Boot has culled together our picks for their Top 10. Read on to see what makes the list:

  • 10

    "If You Ever Stop Loving Me"

    From 'You Do Your Thing' (2004)

    "If You Ever Stop Loving Me" was the debut single from Montgomery Gentry's fourth studio album, and their first No. 1 hit. Written by hitmakers Rivers Rutherford, Tom Shapiro and Bob DiPiero, the song promises that any storm can be weathered as long as romance stays alive.

    "I think Rivers and Tom and I were totally in the same place when we sat down to write this song," DiPiero told The Boot. "We're really unique individuals, and to have a wife and someone who gives day in and day out ... we realized how lucky we are. I think we were all in that same universal space of 'I'm all right, I'm okay / Ain't nothing but another day / But only God knows where I'd be / If you ever stop loving me.'"

  • 9

    "Roll With Me"

    From 'Back When I Knew It All' (2008)

    Neither of the Montgomery Gentry guys wrote "Roll With Me" -- the song was penned by Gary Hannan, Phil O'Donnell and Trent Willmon -- but they both felt like the message of the song was one they could relate to. The pair knew that they could easily sing the lyrics "Back when a pitcher of beer and a couple shots made me bulletproof / Back when God was a name I used in vain to get a point across when I got ticked off / Lord, I'm learning so much more / Than back when I knew it all" every night.

    “When we heard the song, we knew it was a hit for Montgomery Gentry off the bat,” Gentry said. “A buddy of ours, Trent Willmon, a writer on that song, brought the song to us and we just kinda knew it was a hit. In listening to the song, it just reminds us of the days growing up -- it reminded me of all the do’s and don'ts coming from Mom and Dad -- you know, the path of life that shoulda been taken.”

  • 8

    "Lucky Man"

    From 'Some People Change' (2006)

    Montgomery Gentry wrote this song together, along with Rutherford and Mark Wright. The song, which features lines such as, "I got supper in the oven, a good woman's loving / And one more day to be my little kid's dad / Lord knows I'm a lucky man," encourages focusing on the good parts of life, even among the trials -- and apparently it's a song that resonated with listeners. "Lucky Man" stayed at the top of the charts for two weeks and earned Montgomery Gentry their only Grammy nomination to date, for Best Country Vocal Performance By a Duo or Group.

  • 7

    "Daddy Won't Sell the Farm"

    From 'Tattoos & Scars' (1999)

    "Daddy Won't Sell the Farm" was written as a story about a farmer who refuses to give in to the urban growth in his hometown. With lines such as, "You can't roll a rock up a hill that steep / You can't pull roots when they run that deep / He's gonna live and die in the eye of an urban storm / Daddy won't sell the farm," the song resonated with fans all over the country, making it a mainstay at MG's concerts almost 20 years later.

  • 6

    "She Couldn't Change Me"

    From 'Carrying On' (2001)

    "She Couldn't Change Me" was the only Top 20 song from Montgomery Gentry's sophomore album, Carrying On. Written by Gary Nicholson and Chris Knight, the song tells the story of a man who lost, then found, love when his significant other realized she couldn't change his cowboy ways. With lines that include "She called and said she'd been thinkin' about / All those quiet country nights / And whatever she thought was so wrong with me / Suddenly seemed all right," the tune became a Top 40 hit on the all-genre Billboard 100 chart as well.

  • 5


    From 'My Town' (2002)

    Written by Jeffrey Steele and Chris Wallin, "Speed" was driven into the Top 5 in part by its attention-getting video. Directed by Trey Fanjoy, Montgomery Gentry sang the song for the video while standing on a two-lane road in the middle of the night.

  • 4

    "My Town"

    From 'My Town' (2002)

    The title track of Montgomery Gentry's third studio album, the anthemic "My Town" was perfect for the two Bluegrass State natives. With lines that say, "Where I was born, where I was raised / Where I keep all my yesterdays / Where I ran off 'cause I got mad / And it came to blows with my old man / Where I came back to settle down / It's where they'll put me in the ground / This is my town," "My Town" became the battle cry for fans all over the country who were proud of their small-town heritage.

  • 3

    "Where I Come From"

    From 'Rebels on the Run' (2011)

    Much like "My Town," Montgomery Gentry felt compelled to record "Where I Come From" as a way to pay tribute to their rural roots.

    "This says, 'Don’t you dare talk about my town until you’ve been around the block with me. Let me show you what’s going on here,'" Gentry explained to The Boot. "It’s a pretty cool tune, a well-written tune."

    "It’s ‘My Town’ with an attitude," adds Montgomery. "I love the song. It doesn’t matter where you go in this world, you always take a little piece of your home with you."

  • 2

    "Hell Yeah"

    From 'My Town' (2002)

    A song bound to get the crowd on their feet -- or at least be turned up loud on the radio -- "Hell Yeah" summarizes what fans love about Montgomery Gentry. It features lyrics such as "Hell yeah / Turn it up / Right on / Hell yeah / Sounds good / Sing that song / Guitar man playin' all night long / Take me back to where the music hit me / Life was good and love was easy" and includes a chorus of people chanting "hell yeah!" that was recorded at least in part by employees at MG's then-record label, Columbia Nashville.

  • 1

    "Something to Be Proud Of"

    From 'You Do Your Thing' (2004)

    This is the song that sums up everything Montgomery Gentry believes in, and it's authenticity paid off: It became their second chart-topping single. "Something to Be Proud Of" says, in part, "You don't need to make a million / Just be thankful to be workin' / If you're doing what you're able / And putting food there on the table / And providing for the family that you love / That's something to be proud of," hearkening back to Montgomery and Gentry's blue-collar roots, which have served as their inspiration for much of their career. "Something to Be Proud Of" was also the title track of the duo's first compilation album, Something to Be Proud Of: 1999-2005.

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