Eddie Montgomery is a bona fide country music star, but he doesn’t forget where he came from.
In fact, he still lives there, outside of Lexington, Kentucky. Montgomery and his longtime friend and bandmate Troy “T-Roy” Gentry got their start playing together at the Lexington bar that Gentry’s father owned. “I am the last holdout. Everybody else lives in Nashville, [Tennessee],” Montgomery says, referring to Gentry and younger brother John Michael Montgomery, who became the first country music standout in the family. “T-Roy lives in Nashville. He is better with the business end of things. Nashville is only three hours away. If they need me, I can come up there.”
Eddie, who just turned 52, learned how to be tough growing up poor with divorced musician parents. The blue-collar life served Eddie and Gentry well, as they have both encountered personal hardships throughout their journey to stardom.
Eddie was diagnosed with cancer in November 2010. Shortly after, his ex-wife, Tracy, filed for divorce. The two had been married for 20 years and had four children. “I am going to tell you if you don’t live life, nothing is going to happen. If you live life, you are going to have adversity,” Eddie says. “You have to live life and have as much fun as you can.”
Eddie, who married his second wife, Jennifer, in 2014, was again dealt another tragic blow Sept. 27 when his 19-year-old son, Hunter, died after an accident.
Music was an important part of the Montgomery family. The Montgomery boys grew up in area honky-tonks while their parents played in a band. Eddie joined his parents’ band, playing the drums at 13. “There was the joke that [Mom and Dad played], and the bartenders were the babysitters,” he says. While the family’s situation was less than ideal, Eddie says he has fond memories of childhood.
“I think we grew up so poor that one thing we always had was music and our friends,” he says. “At Christmas, we didn’t have a lot of toys, but we had music and a bunch of friends around. We lived life and learned that there are going to be ups and downs, but the main thing is to love life and have fun and embrace it. It is very short, so you need to live it.”
As they got older, Eddie and Gentry played music with John Michael as part of Early Tymz, the house band at Austin City Saloon in Lexington. When John Michael headed to Nashville in 1991, the friends continued to play and tour regionally. In 1994, Gentry won the Jim Beam National Talent Contest and tried to forge a solo career. He opened for acts such as Patty Loveless and Tracy Byrd. However, after Gentry failed to earn a record deal, the two friends reunited and formed Montgomery Gentry in 1999. John Michael convinced record execs to scout the duo, and in 1999, Montgomery Gentry had its first record deal.
The album Tattoos & Scars’ debut single, “Hillbilly Shoes,” entered the Billboard country charts two weeks before its scheduled release date. It hit No. 62 on the Billboard Hot 100. “Lonely and Gone” was the second single and peaked at No. 5 on the Hot Country Songs chart by the end of the year.
The instant success of the album won the duo Top New Vocal Duet or Group from the Academy of Country Music in 1999 and Favorite New Artist-Country at the 2000 American Music Awards.
After all those years playing honky-tonks in Kentucky, Montgomery Gentry had arrived. They followed up the debut with the successful 2000 album Carrying On and then released My Town with the successful single of the same name.
Montgomery Gentry have released six studio albums and have produced 20 chart singles. The group also produced five No. 1 hits on the Hot Country Songs chart: “Back When I Knew It All,” “If You Ever Stop Loving Me,” Lucky Man,” “Roll With Me” and “Something to be Proud Of.”
“We have been so lucky,” Eddie says. “We have some great songs, but I would say ‘My Town,’ ‘Lonely and Gone’ are sung back louder [from the audience]. The feeling gets through.”
Montgomery Gentry released their seventh album, Folks Like Us, in June, their first since 2012.
“I love it. It is still the way we feel about America, family and faith,” Gentry says. “[Producer] Michael Knox has given us a fresh sound, but we are singing about all of the things we have grown up singing about.”
Decades later, the friends are still playing music, recording albums and touring. Their latest tour stops Friday at the Arkansas State Fair as a headlining act for the two-week event.
“We are road dogs and grew up in the nightclubs. I have been off four days in the last 40,” Gentry says. “We love playing music and hanging out and having fun.”
A lot has changed since they started playing together with John Michael in that band, but the one thing that remains the same for the two: their close relationship.
“We have put our friendship before the whole thing. We have known each other longer than we have known our wives, Eddie says. “I reckon it is because of the stuff we have gone through together in the nightclubs and the things that have happened. We have always been there for each other, and things have always worked out.”
Montgomery Gentry play 8 p.m. Friday on the Wendy’s Main Stage.