Eddie Montgomery looks at the 20 years he and Troy Gentry spent as Montgomery Gentry not as a timeline of a career, but a party. The duo's journey is commemorated on Montgomery Gentry: 20 Years of Hits, a project that highlights the songs that made them one of the most celebrated acts in the country music.

The album features 12 of their most notable hits, several of which are retooled into new versions featuring Brad Paisley, Darius Rucker, Jimmie Allen, Logan Mize and more.


The album brings to life the memory of Gentry, who was tragically killed in a helicopter crash in 2017. The songs were re-recorded before his untimely death. "When we picked songs, we were pretty hardcore on them," Montgomery describes to Taste of Country about how he and Gentry selected their career-defining hits. "They've always to me meant life or part of my life that I've been through."

Montgomery Gentry made it to Music City by way of their native Kentucky when representatives from the city saw the talent the two singers possessed, and took them out of the bars where they performed nightly and into the Nashville machine. But those days performing for hometown crowds served as a crucial part of the journey, one where Montgomery gathered inspiration for songs and the people they sing about.

"That's just the way it was, playing six nights a week in a honky-tonk four or five hours a night. You hear stories when people come in, and you go, 'I'm going to sing your story,'" Montgomery says.

And the duo did exactly that, establishing an expansive catalogue of songs that often celebrate life and express gratitude. "Hell Yeah," "My Town" and "Something to be Proud Of" are among the defining tracks that earned the duo longtime fans and the endurance of a career spanning 20 years.

Performing these songs over the course of two decades means new memories are created each time they sing them. Montgomery recalls a July 4 show in Gulf Shores, Ala. when a fan stormed the stage, fittingly during "One in Every Crowd." The man attempted to swan-dive into the audience—a decision that left him face-down on the concrete and sent him home with 300 stitches.

"Of course when he was going out, they're carrying him out on a gurney, he just put his thumb up," Montgomery laughs of the memory. "I know I'll never forget it...I'll bet you he don't ever forget it either."

Rodney Atkins is a featured vocalist on "One in Every Crowd" on 20 Years of Hits, along with the many other guests who wanted to lend their voices to songs by a duo they've admired for years. Rucker sings on "Lucky Man," while Paisley adds his touch to "Back When I Knew it All." Allen and his father were friends of Gentry's, and the up-and-comer chose to be a part of "Hell Yeah."

But the album's purest moment comes with "Better Me." One of the final songs on the project, it finds Gentry on lead vocals, offering an autobiographical look at a person working to improve themselves. It originally appears on their 2018 album Here's To You, and is symbolic of Gentry's state of mind in the months leading up to his passing. 

"I think that's where T-Roy was in his life, he was getting there and that's what he wanted to be," Montgomery reflects. "When that song come up, that's the first song that he ever really come to me and was like 'Eddie, man, if you don't care, I'd like to sing this song.'"

Montgomery says he thinks of his loyal friend daily. He recently revisited the storage unit that houses old memories and memorabilia from all facets of their career, including photos from their days in the bars before they made it big; one of them posing in front of a limousine that was taking them to Nashville, where they'd eventually leave their mark on country music.

"T had a big ole wooden spoon and he carried that around because he was always stirring up stuff and going to pull something. We always was doing crazy stuff and just living life," Montgomery reflects. "When I get in the storage units or when I hear the songs—hear T's voice—I just think of that big smile."

Montgomery Gentry: 20 Years of Hits is available now.

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