A native of Danville, Kentucky, Eddie Montgomery was born on September 30, 1963. He began playing drums in the family band Harold Montgomery and the Kentucky River Express when he was 13. Eddie's familial bond continued in Early Tymz, an early-'90s outfit that featured his younger brother John Michael as well as Troy Gentry. This trio continued as Young Country after Early Tymz split. Following John Michael Montgomery's pursuit of a solo career -- he released his debut Life's a Dance in 1992 -- Troy Gentry also attempted to fly on his own, but once that dream didn't pan out, he reunited with Eddie Montgomery to form Deuce. By the time they'd signed to Columbia Nashville, the duo had changed their name to Montgomery Gentry.
Columbia released "Hillbilly Shoes," the first single from Montgomery Gentry's debut album, Tattoos Scars, early in 1999. Later in the year, "Lonely and Gone" gave the duo their first Billboard Country Top Ten, its peak of number five eclipsed in 2001 by the number two placement of "She Couldn't Change Me," the first single from the pair's second album, Carrying On. Montgomery Gentry's hot streak officially started with My Town in 2002, with the record generating three Top Ten hits ("My Town," "Speed," "Hell Yeah"). They first topped the charts with "If You Ever Stopped Loving Me" in 2004, reaching that pinnacle again a year later with "Something to Be Proud Of," both singles pulled from 2004's You Do Your Thing. The 2006 album Some People Change kept the group's streak alive with the 2007 number one "Lucky Man," while 2008's Back When I Knew It All delivered back-to-back number ones with "Back When I Knew It All" and "Roll with Me."
Montgomery Gentry left Columbia Nashville after Back When I Knew It All, moving to Average Joes Entertainment for Rebels on the Run in 2011. The album gave Montgomery Gentry their last Country number one with the anthemic rallying call "Where I Come From," which reached eight in 2011. The duo moved to Blaster Records for 2015's Folks Like Us. Montgomery Gentry returned to Average Joes in 2017 and were working on a new album when Troy Gentry died in a helicopter crash in 2017. Eddie Montgomery completed the album, now titled Here's to You in tribute to his departed colleague; it was released in February 2018.
Montgomery revisited the duo's songbook on 20 Years of Hits, a 2018 album featuring new recordings of old tunes cut while Gentry was still alive; many tracks featured such guests as Brad Paisley, Jimmie Allen, and Darius Rucker. Montgomery was inducted into the Kentucky Country Music Hall of Fame in 2018. In 2019, he closed the books on Montgomery Gentry with Outskirts, a record featuring previously unreleased recordings with Gentry. That same year, Montgomery released the digital solo singles "Lucky Scars" and "Be a Cowboy (PBR Anthem)."
Eddie Montgomery continued to tour as Montgomery Gentry into the 2020s. His solo debut album, Ain't No Closing Me Down, arrived via an exclusive retailer in October 2021; it received a wider release in January 2022. Later that year, Montgomery published Police Officers, Our Friends!, a children's book written in collaboration with Randy Graham. ~ Stephen Thomas Erlewine, Rovi