Remembering Montgomery Gentry’s Troy Gentry + What He Spoke For

Has it really been five years since Troy Gentry died?

On September 8, 2017, Gentry took a helicopter ride before a show in Medford, N.J. Pilot error and a failure by maintenance personnel were eventually blamed for a crash that killed the 50-year-old Montgomery Gentry guitarist.

Eddie Montgomery was waiting for his longtime friend at the airport. "There’s not a day that I don't see it," he'd later tell Taste of Country.

Gentry left behind wife Angie and two children. He also left behind millions of broken-hearted fans who identified with songs like "Something to Be Proud Of," "Hell Yeah" and "Hillbilly Shoes."

To acknowledge the anniversary, we put together a short video of interview clips that show what Gentry preferred to talk about above all else. He was not a perfect human being, but he had a big heart. Watch the video at the top of this article.

In the months that followed, Montgomery was quiet, but in early 2018, he began to talk about the tragedy and his friend, whom he considered a brother. He'd tell ToC that he and Gentry talked about what the other should do if one of them died unexpectedly — the marching orders were to keep the Montgomery Gentry music alive, so that's what he did. A tour and a new album followed, and then even more new music.

Now 58 years old, Montgomery is touring as Montgomery Gentry and a solo artist, having released his first solo album in 2021. He recognized Gentry's death on social media on Thursday (Sept. 8).