Montgomery Gentry: 10 Prime Hits

It’s hard to believe that it’s been just over 20 years ago that Montgomery Gentry’s Eddie Montgomery and Troy Gentry made their world debut with “Hillbilly Shoes;” their first of many signature songs.

Although it peaked at No. 13 in 1999, the loud and proud country rocker immediately stood out on the airwaves and reintroduced authentic outlaw attitude back into the mainstream in a year when songs like Lonestar’s “Amazed,” Kenny Chesney’s “How Forever Feels” and Martina McBride’s “I Love You” were more the trend.

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The duo won the CMA for vocal duo of the year in 2000 and joined the Grand Ole Opry in 2009. Tragically, Gentry died in a helicopter crash that was caused by a pilot error on Sept. 8, 2017.

In a 2018 interview, Montgomery detailed the duo’s plan to continue making music in the event one of them died, saying, “There’s never going to be another T-Roy. He was so full of life. And I want to make sure nobody ever forgets Troy, and I want to make sure nobody ever forgets Montgomery Gentry.”

Gentry’s memory is eternal because of Montgomery Gentry’s music. Today, on what would have been his 52nd birthday, the staff revisits 10 of its favorite performances:

  1. “Hillbilly Shoes”

    Songwriters: Mike Geiger, Woody Mullis and Bobby Taylor

  2. “Lonely and Gone”

    Songwriters: Greg Crowe, Dave Gibson and Bill McCorvey

  3. “She Couldn’t Change Me”

    Songwriters: Chris Knight and Gary Nicholson

  4. “My Town”

    Songwriters: Reed Neilson and Jeffrey Steele

  5. “Hell Yeah”

    Songwriters: Jeffrey Steele and Craig Wiseman

  6. “Gone”

    Songwriters: Bob DiPiero and Jeffrey Steele

  7. “Something to Be Proud Of”

    Songwriters: Jeffrey Steele and Chris Walin

  8. “Lucky Man”

    Songwriters: David Lee and Dave Turnbull

  9. “Back When I Knew It All”

    Songwriters: Gary Hannan, Phil O’Donnell and Trent Willmon

  10. “Roll With Me”

    Songwriters: Clint Daniels and Tommy Karlas

Lauren Tingle is a Tennessean and storyteller who eats music for breakfast, lunch and dinner. When she’s not writing or rocking out, she enjoys yoga and getting lost in the great outdoors.