Montgomery Gentry were a country music duo compromised of vocalists Eddie Montgomery and Troy Gentry, both hailing from Kentucky.

The duo have released six albums for Columbia Records' Nashville division: Tattoos & Scars (1999), Carrying On (2001), My Town (2002), You Do Your Thing (2004), Some People Change (2006), and Back When I Knew It All (2008) as well as a Greatest Hits album. Tattoos and Scars, My Town and You Do Your Thing are all certified platinum.

The duo have had more than 20 singles on the Billboard Hot Country Songs charts (USA), including five #1 singles (If You Ever Stop Loving Me, Something To Be Proud Of, Lucky Man, Back When I Knew It All and Roll With Me).

Montgomery Gentry left Columbia Records in 2010 and signed to Average Joes Entertainment, a label co-owned by country rap singer Colt Ford. With this label, the duo released Rebels on the Run, their seventh album.

As of 2014, the duo are signed to Blaster Records, and released their eighth album, Folks Like Us, on June 9, 2015.

The duo won the 1999 AMA for Favorite New Artist – Country. They also won the CMA award for Duo of the Year in 2000, an award for which they were nominated every year between 1999-2009. Montgomery Gentry were nominated for a Grammy for Best Country Vocal Performance by a Duo or Group for their song Lucky Man in 2008. The duo were inducted into the Grand Ole Opry in 2009. The duo were also nominated every year between 2001-2009 for the Academy of Country Music’s Top Vocal Duo. On Sept 8-2017 Troy Gentry passed away in a helicopter crash in Medford Township, NJ