You can rewind and review his career. You can reminisce about his formative years, the pre-celebrity era, spent in Lexington. You can even admire the combination of performance stamina and mainstream popularity that kept the band that bore his name popular for close to two decades. But when the parting is so sudden and tragic, the impact of the exit winds up being what — for the moment, at least — sticks with you.
That was the feeling that hit when I got a call late Friday afternoon that started with the three words you don’t want to hear in lieu of hello.
“Have you heard…”
That’s when the news began to quickly spread about the New Jersey helicopter crash that took the life of Troy Gentry, the Lexington-born half of Montgomery Gentry. Gentry had long ago relocated to Nashville, but for most any Lexington country music fan, he will always be a local hero. It was here that he played weekends at the Austin City Saloon with siblings John Michael and Eddie Montgomery. When John Michael’s career took off in the early 1990s, Gentry re-teamed with Eddie and forged a duo act through steady gigging at the Tates Creek Centre nightspot known as The Grapevine. By 1998, Montgomery Gentry was formed, signed and on its way to stardom.
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At the height of the duo’s commercial popularity, around the time its third and fourth albums — 2002’s “My Town” and 2004’s “You Do Your Thing” — were nearing platinum status, Montgomery Gentry became a regular at Rupp Arena. One could only imagine the sense of accomplishment that must have come from singing the hit title tune to “My Town” in the big house of their hometown first at a show opener for Kenny Chesney and then as headliner for several New Year’s Eve performances.
Blending Southern rock inspiration with ample country bravado, Montgomery Gentry relished its role as a leading Central Kentuckv voice for contemporary country music. While the hits began to get sparser in recent years and the returns to their hometown became less frequent, the two never lost their popularity as a national touring act or as a local success saga.
“Playing the clubs then, you had The Greg Austin Band, Doug Breeding, Larry Redmon,” Gentry told me of his early club dates with the Montgomery brothers, in a 2014 interview. “Lexington was booming with live music. On the weekends you weren’t working or in between breaks on nights that you were, you would try and zip over to one of the other clubs and check out some of the other music.
“Then John Michael was discovered. But what was really fascinating was the fact that Eddie and I kept playing together. We were fortunate enough that we had something unique and different that Nashville heard about. So it’s pretty cool that we all played together in one band, split up and still make a career out of doing what we love to do.”