In the 1990s, Kentucky natives Eddie Montgomery and Troy Gentry formed a band together, dubbing themselves Montgomery Gentry after their respective surnames. Releasing six albums, Montgomery Gentry specialized in “blue-collar anthems” celebrating “the good, the bad, the ugly and the party on the weekend.” Following Gentry’s tragic death in 2017, his bandmate continues performing all their beloved hits in his honor, including No. 1 songs like “Something to Be Proud Of” and “Lucky Man”. Today (April 5), we’re remembering Troy Gentry on what would have marked his 59th birthday.
Troy Gentry First Tried His Hand as a Solo Artist
Born April 5, 1967, in Lexington, Kentucky, Gentry graduated from Lexington Community College before attending the University of Kentucky.
Becoming a fixture on the local club scene as a teenager, he joined the band Early Tymz in 1990 with brothers Eddie and John Michael Montgomery. After that group’s split, they formed a new group, Young Country, with John Michael at the helm.
Eventually, the “Be My Baby Tonight” crooner left for a solo career. Troy Gentry briefly pursued the same path. However, despite winning the Jim Beam National Talent Contest in 1994 and landing opening gigs for Patty Loveless and Tracy Byrd, he never managed to secure a record deal.
Reuniting with former bandmate Eddie Montgomery, the newly-minted Montgomery Gentry signed with Columbia in 1999.
The duo’s debut single, “Hillbilly Shoes”, enjoyed such widespread radio success that Montgomery Gentry wound up releasing their freshman album, Tattoos & Scars, a month early.
After several more successful singles and a platinum album, Eddie Montgomery and Troy Gentry dethroned Brooks & Dunn as the Country Music Association’s Duo of the Year in 2000.
Their No. 1 hits included “If You Ever Stop Loving Me,” “Something to Be Proud Of,” “Lucky Man,” “Back When I Knew It All” and “Roll With Me.” In 2009, the duo punched their ticket to the Grand Ole Opry.
“A Horrific Day”
Montgomery Gentry’s days as a duo came to a tragic end on Sept. 8, 2017. Hours before a scheduled show at the Flying W Airport and Resort in Medford, New Jersey, Troy Gentry joined pilot James Evan Robinson on a Schweitzer 269 helicopter for a sightseeing flight.
Engine problems led the plane to crash into a wooded area short of the runway, killing Robinson on impact. Rushed to a nearby hospital, Gentry died later that day. He was 50 years old.
Recalling the “horrific day” in an interview with People, Eddie Montgomery said, “A little piece of my soul got lost there… It’s something that you never get over.”
The country musician left behind wife Angie Gentry and two daughters, Taylor and Kaylee.
Featured image by Frazer Harrison/ACMA2010/Getty Images for ACMA