Eddie Montgomery Thinks Late Montgomery Gentry Bandmate Troy Gentry Is Playing Pranks on Him

by Clayton Edwards

If you were listening to country radio in the late 90s and early 2000s, you remember Montgomery Gentry. They dropped their first record Tattoos and Scars in 1999. Then, they released five more albums over the next nine years. Chart-toppers like “If You Ever Stop Loving Me,” “Lucky Man,” and “Roll With Me” were all over the radio. Unfortunately, one half of the dynamic duo, Troy “T-Roy” Gentry died in a helicopter crash in 2017. However, he and Eddie Montgomery made a pact before his passing. They swore that if one of them died, the other would keep the band alive. Montgomery stayed true to his word.

Eddie Montgomery didn’t just keep his and Gentry’s band alive. He also set to work on crafting a solo album. Ain’t No Closing Me Down hit shelves on October 29. The album sees Montgomery opening up about the pain of losing two sons as well as a bandmate and close friend. Additionally, he collaborated with 90s icon Tanya Tucker for a track on the album. That’s not the only collaborative effort behind the record, though. Montgomery says that Gentry was there with him every step of the way.

In an interview with Taste of Country, Eddie Montgomery said, “As I was writing the songs, I think [Troy Gentry] was helping me. I think he’s always helping me.” It makes sense that Troy’s spirit would be there with him. They were close friends. So, why wouldn’t Gentry’s spirit help guide Montgomery through the process of opening his heart through his songwriting?

Eddie Montgomery Says Troy Gentry Pranks Him

Eddie Montgomery added that there are times when T-Roy is a little less helpful. However, he’s not complaining. He’s just glad to know that his old buddy is still around. He gave Taste of Country an example of Gentry’s jokes from the Great Beyond.

Eddie Montgomery still plays live shows under the Montgomery Gentry banner. That’s when Gentry’s activity really picks up. “While we’re on the shows, I mean I’ve had stuff happen, man, I’m going ‘Okay, that’s T-Roy pulling a prank,” he said. “Like going out and the PA just shuts off. I’m going ‘What? Ah, that’s T-Roy, man, letting us know.”

From the outside looking in, something like shutting off the PA system during a show doesn’t seem like help. However, we have to take into consideration how Eddie Montgomery has to feel when he takes the stage under the MG banner. He’s spoken several times about how much he misses his late bandmate and friend. So, standing on the stage with their band singing their old songs has to bring back countless bittersweet memories. With that in mind, having some sign that Gentry is still there, watching over him, must be comforting.