A Biography and Song List of Duo Montgomery Gentry

All About the Rowdy, Rockin' Country Duo

Montgomery Gentry
Montgomery Gentry. Rick Diamond/Getty Images Entertainment/Getty Images

Musicians Eddie Montgomery and Troy Gentry are the band Montgomery Gentry.

Gerald Edward Montgomery was born on September 30, 1963, in Danville, Kentucky. He began performing with his parents' band, Harold Montgomery, and the Country River Express, as a child. He joined the band full time when he was 13, replacing his mom on the drums. 

Troy Lee Gentry was born on April 15, 1967, in Lexington, Kentucky where he spent his teenage years performing guest vocals with local bands and eventually started a group with Eddie Montgomery and Eddie's younger brother, John Michael.

The First Band 

The country duo's first band together was called Young Country, but Troy decided he wanted a solo career after two years. He left the band in 1994 and entered the Jim Beam National Talent Contest. He won and got to open for Patty Loveless and Tracy Byrd. But nothing ultimately came of his solo career. Troy eventually paired up with Eddie again and they formed a duo they called Montgomery Gentry.

They took to the honky-tonks and the bars of Kentucky to build their fan base before heading to Nashville where they were signed by Columbia Records in 1999.

Career Overview

Montgomery Gentry released their debut album, Tattoos & Scars, in 1999. The first single, "Hillbilly Shoes," hit the Billboard charts two weeks before it was scheduled to and it peaked at number 13. The album was released a month early because there was such high radio demand for the song. Montgomery Gentry won the Country Music Award for Best Vocal Duo of the Year in 2000, an award that had been held by Brooks & Dunn for eight consecutive years. Tattoos & Scars, noted for its Southern rock influences, was certified platinum in 2001.

Montgomery Gentry's sophomore release, Carrying On, was released in 2001. It cracked the country chart's Top 10 and produced hits like "She Couldn't Change Me," which marked the duo's first Hot 100 appearance. Carrying On wasn't as well-received as Tattoos & Scars, possibly due to the album's noticeably edgier sound, but it went gold regardless.

My Town was released in 2002, earning the duo their third Top 5 single with the album's title track. A new producer and new musicians contributed to My Town's invigorating rock sound, and the album was certified platinum. You Do Your Thing came out in 2004, another platinum album, followed by Something to Be Proud Of, a greatest hits compilation, in 2005. Some People Change was released in 2006 and Back When I Knew It All appeared in 2008. This string of albums amounted to a great deal of success. At least a dozen of Montgomery Gentry's singles, as well as their albums, made it to the Top 10.

Then the duo hit a rough patch. Their 2009 album Freedom was scrapped and their label, Columbia, decided to release Hits and More: Life Beside a Gravel Road instead. It was another greatest hits album that included three new songs. A day before Gravel Road was to be released, Montgomery Gentry exited the label due to creative differences and the album was shelved.

They signed to Average Joes Entertainment and released their seventh studio album, Rebels on the Run, in 2011. The album features the duo's classic sound and critics noted its similarities to their works like Some People Change. Coming off of an extensive tour in 2012 and 2013, the pair signed to Blaster Records and released Folks Like Us in June 2015.


  • Tattoos & Scars (1999)
  • Carrying On (2000)
  • My Town (2002)
  • You Do Your Thing (2004)
  • Something to Be Proud Of - The Best of 1999-2005 (2005)
  • Some People Change (2006)
  • Back When I Knew It All (2008)
  • Folks Like Us (2015)

Popular Songs:

  • "Roll With Me"
  • "Lucky Man"
  • "What Do Ya Think About That"
  • "Back When I Knew It All"
  • "Where I Come From"
  • "Hillbilly Shoes"