In 1999, Montgomery Gentry signed their first record deal. Between then and when Troy Gentry was killed in a helicopter crash on Sept. 8, 2017, the duo released eight studio albums. Although the majority of their songs came from outside songwriters, Gentry and duo partner Eddie Montgomery did occasionally help co-write their material; Gentry specifically co-wrote eight of the songs that Montgomery Gentry released during his lifetime.

Below, readers can listen to the eight Montgomery Gentry songs that Gentry himself helped write. The first came on the duo's 2001 album Carrying On; the songs are arranged chronologically, so that listeners can hear how Gentry's writing progressed.

ACM Top New Vocal Duo or Group and CMA Vocal Duo of the Year winners and Grand Ole Opry members, Montgomery Gentry earned three platinum albums and five No. 1 singles. They last released an album, Folks Like Us, in 2015, though their current label, Average Joes Entertainment, says that Gentry and Montgomery had completed a new album shortly before Gentry's death.

Flip through the photo gallery above to re-live some of Montgomery Gentry’s biggest career milestones.

  • "Lucky to Be Here"

    From 'Carrying On' (2001)

    Written by Troy Gentry, Kenny Beard and Eddie Montgomery

  • "Talking to My Angel"

    From 'You Do Your Thing' (2004)

    Written by Troy Gentry, Michael Dulaney and Jason Sellers

  • "Takes All Kinds"

    From 'Some People Change' (2006)

    Written by Troy Gentry, Neil Thrasher and Michael Dulaney

  • "If You Wanna Keep an Angel"

    From 'Some People Change' (2006)

    Written by Troy Gentry, Tom Shapiro and Rivers Rutherford

  • "Simple Things"

    From 'Rebels on the Run' (2011)

    Written by Troy Gentry, Wendell Mobley and Neil Thrasher

  • "Work Hard, Play Harder"

    From 'Rebels on the Run' (2011)

    Written by Troy Gentry, Jim Collins and Rivers Rutherford

  • "Freedom Never Goes Out of Style"

    From 'My Country, Vol. 2: Smash Hits' (2011)

    Written by Troy Gentry, Eddie Montgomery, Gary Hannah and Phil O'Donnell

    This song was meant to be on Freedom, what would have been Montgomery Gentry's seventh studio album with Columbia Nashville; however, the duo left the label before the record could be released. In 2012, Jackson Delaney released a version of "Freedom Never Goes Out of Style" on his self-titled album.

    Audio of "Freedom Never Goes Out of Style" is unavailable for embedding.

  • "Titty's Beer"

    From 'Mud Digger, Vol. 4' (2013)

    Written by Troy Gentry, Tim Nichols and Craig Wiseman

    Colt Ford also released a version of this song, on his Every Chance I Get album, featuring Trent Tomlinson.