After gaining some local fame as Early Tymz, the Montgomery brothers and Troy Gentry parted ways when John Michael began his own solo career. Gentry won a talent contest sponsored by Jim Beam in 1994, and reunited with Montgomery. The two signed to Columbia Records in 1999 and had a breakout success with "Hillbilly Shoes" that year. Following it was "Lonely and Gone", their first Top 5 hit. Their debut album, Tattoos & Scars, earned a platinum certification.
The duo continued through most of the 21st century's first decade with steady chart presence and album sales, culminating in their first #1 hit "If You Ever Stop Loving Me" in 2004. Other big hits during the first stretch of their career included "She Couldn't Change Me", "Hell Yeah", "Speed", "If You Ever Stop Loving Me" (their first #1), "Something to Be Proud Of", and "Gone". Although most of their big hits were country-rock uptempos, they began adding a few ballads into the mix over time, particularly on Some People Change, whose title track was a cover of Kenny Chesney. Additional #1 hits came from Back When I Knew It All with the title track and "Roll with Me", which featured guest vocals from Five for Fighting.
After an unreleased album on Columbia, they moved to Average Joes Entertainment for one last hit in "Where I Come From", followed by a string of unsuccessful independent albums. Gentry died in a helicopter crash in September 2017, right before the release of Here's to You. Montgomery continued to tour under the Montgomery Gentry name in 2018, using members of their road band to compensate.
The duo is known for its country-rock edge mixed with passionate ballads, along with the contrast between Montgomery's and Gentry's singing voices.
- Tattoos & Scars (1999)
- Carrying On (2001)
- 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)
- Rebels on the Run (2011)
- Folks Like Us (2015)
- Here's to You (2018)
- Accent On The Wrong Syllable: "Speed" has "Can it get me / O-ver her quickly".
- Blah Blah Blah: "What Do Ya Think About That" has the line "Sayin' blah blah blah, just jackin' their jaws"
- Cheap Heat: "Lucky Man" did this with the lyric "Last Sunday, when my Bengals lost, Lord, it put me in a bad mood". Depending on the market, "Bengals" was replaced with the local NFL franchise.
- The City vs. the Country: "Daddy Won't Sell the Farm" is about a farmer who refuses to sell his land, even when suburbia crops up around him.
- Country Rap: Minor example, as "If You Ever Stop Loving Me" has a turntable scratch.
- "Humoresque" Progression: "Where I Come From".
- Past In The Rearview Mirror: In "Speed", the narrator mentions that he's tearing the rearview off the car he's buying to put distance between him and his ex.
- Rearrange the Song: "Gone" had Eddie's backing vocals amplified on the verses, and made several abrupt cuts in the instrumentation (such as the organ solo before the last chorus, and the fadeout).
- Singer Name Drop: Eddie sings "A few close friends, Charlie, Troy, and me" in "All Night Long", a duet with Charlie Daniels. He also sings "Maybe later on, me and ol' T-Roy will show you 'round our town" in "My Town".
- Taking the Kids: "I'll Keep the Kids" has the narrator telling his wife that she can take whatever she wants, including his favorite shirt that he hopes fits old what's-his-name, but that he'll keep the kids.
- Vocal Tag Team: Most of their big hits are duets between the two, usually with one on the verses and the other on the chorus, although some songs feature only one of the two singing lead and the other harmonizing. Interestingly, this was averted early on: Troy sang their debut single "Hillbilly Shoes", but Eddie sang every other single until "My Town", which established the "one sings the verses, the other sings the chorus" pattern used on most of their subsequent releases.