Gone Four Years Now, Troy Gentry of Montgomery Gentry Was All Smiles

by Jim Casey

Troy Gentry was killed in a helicopter crash on Sept. 8, 2017. Of course, Troy was one-half of the award-winning duo, Montgomery Gentry, with partner Eddie Montgomery.

It’s hard to believe it has been four years since Troy, 50, died. It’s even harder for me to believe all of the country stars we’ve lost over the last four years, everyone from Glen Campbell (2017) and Roy Clark (2018) to Kenny Rogers (2020), John Prine (2020), and Charley Pride (2020). However, Troy’s death was especially shocking, not only the manner, but also because Troy was so vibrant in person—always energetic, always smiling. He was a “young 50,” so to speak.

Montgomery Gentry

Eddie and Troy, who had been friends for more than 10 years, formed Montgomery Gentry in 1999. The duo scored a handful of chart-topping hits in the 2000s, including “Something to Be Proud Of,” “Lucky Man,” “Roll With Me,” and more. The tandem also copped the ACM Top New Vocal Duo/Group of the Year in 1999 and CMA Vocal Duo of the Year in 2000.

In fact, Montgomery Gentry is the only tandem not named Brooks & Dunn to win the CMA Vocal Duo of the Year Award in between the years 1992 and 2006. Yep, Kix Brooks and Ronnie Dunn won 14 of 15 CMA Duo of the Year Awards in the aforementioned span. Montgomery Gentry was the hiccup. Fans of country music trivia can store that chestnut for later, because the query pops up from time to time.

I had the opportunity to interview and chat with Troy and Eddie on a few occasions. And I always found them to be earnest, affable, and interesting. It’s always shocking when someone dies suddenly, as Troy did on that September day in New Jersey, only hours before he was scheduled to perform. Troy left behind two daughters and his wife, Angie, among others.

Remembering Troy

Shortly before his death, Troy and Eddie recorded “Better Me,” which was played for the first time at Troy’s celebration of life at the Grand Ole Opry on Sept. 14, 2017. The Grand Ole Opry welcomed Eddie and Troy as members in 2009.

The song was featured on MG’s 2018 album, Here’s to You. After Troy’s death, the touching tune took on a new meaning with Troy’s tenor on lead: “I might cuss and fight, tell a few lies / Break a few rules making promises I can’t keep / But I’ve turned a page on wilder days / I’m writing all this down hoping you’ll see / I ain’t saying I’m perfect, but I’m working on a better me.

Like all of us, I’m sure Troy made some mistakes during his life. He had a well-documented one in 2004 when he illegally harvested a bear. But what I’ll always remember about Troy—in addition to his music—was his dedication to charities like St. Jude Children’s Research Hospital and Make-A-Wish, among others. Troy had a big heart. Maybe bigger than his smile.

While Troy didn’t write “Better Me,” it felt like he embodied the song.

A few months after Troy’s death, Eddie told me, “After that horrific accident, man, the whole world changed. Of course, me and T-Roy had been together almost 35 years. It was losing a brother and a best friend . . . Man, [“Better Me”] is probably the best vocals I’ve ever heard him do.”