After tragedy, Montgomery Gentry marks 25th anniversary on WTOP: ‘No better way to celebrate’

WTOP's Jason Fraley celebrates 25 years of Montgomery Gentry (Part 1)


Tragedy struck Montgomery Gentry when one half of the country-music duo was silenced.

Troy Gentry was killed in a helicopter crash in 2017, and last week, Eddie Montgomery joined Gentry’s widow Angie at a special CMA Fest ceremony in Nashville, Tennessee, to mark the band’s 25th anniversary. There, the Recording Industry Association of America surprised them with three plaques declaring their song “Something to Be Proud Of” as certified platinum, while “My Town” and “Hell Yeah” were both certified gold.

“It was unbelievable because they surprised me with it at the fan club party,” Montgomery told WTOP. “There’s no better way to celebrate it than with all our friends. They’re the reason we got the plaques. … We don’t call anybody fans, we call them friends. Me and T-Roy have been blessed that we’ve got a lot of friends around the world, so it’s been unbelievable.”

Born in Kentucky in 1963, Montgomery grew up in a musical family traveling between honky tonks.

“My mom was a drummer, my dad was a guitar player and the bartenders were our babysitters,” Montgomery said. “By the time we were 8, we were roadies. … When you walked in the door, they asked if you had a gun; if you didn’t, they’d give you one. When you’d come into our house, we didn’t have living room furniture, you’d sit on a guitar amp or a drum throne. … Me and my brother never understood why kids in school weren’t allowed to come over.”

That younger brother was John Michael Montgomery, who burst onto the country music scene first in 1992 with a string of massive hits, including “Life’s a Dance,” “I Love the Way You Love Me,” “I Swear,” “I Can Love You Like That,” “Sold (The Grundy County Auction Incident),” “Be My Baby Tonight” and “The Little Girl.”

“Me and T-Roy and John Boy actually started the band together in Lexington, Kentucky, pretty much out of high school,” Montgomery said. “We were pushing John Boy, so Troy went to work for his dad and left the band. … I went on the road with John Boy for a while until a guy come up to me and said, ‘Are you John Michael’s brother, the drummer?’ That’s when I told my brother, ‘I’m not gonna play the drums anymore.'”

Instead, Eddie and Troy were back home playing in Gentry’s father’s bar when Sony representatives happened to pop in to listen. They liked what they heard, signing the duo to the label in 1997 as Montgomery Gentry dropped their debut album “Tattoos & Scars” (1999), featuring the hit single “Lonely and Gone.”

“Dave Gibson and Blue Miller wrote that song, they played with [Bob Seger’s] Silver Bullet Band,” Montgomery said. “We kept going all over Nashville hunting for songs and of course nobody knew who we were at the time and didn’t know what style we were. At the time it was John Boy and all the love songs coming out … I knew we wanted to be a little more rocking, so we were like, ‘That’s not us, we’re more Skynyrd, Merle Haggard, stuff like that.'”

Their second album “Carrying On” (2001) delivered another hit with “She Couldn’t Change Me.”

“That’s what we were about,” Montgomery said. “We used to hear stories all the time when people would come into the bars and they might be celebrating a new promotion or celebrating because they got fired or they might be celebrating because they got married or they might be celebrating because they got divorced — you never knew. So we decided that everybody that came in or people we’d run into, we were gonna write songs about.”

Their third album “My Town” (2002), featured a title track about their small-town roots.

“Our little small town that we grew up in, well, if you’d blink, you’d miss it. But everybody knew everybody and everybody had each other’s backs,” Montgomery said. “It was awesome growing up and, I tell ya what, that’s why I never moved to Nashville. I’m the last holdout, me and my brother are. We still live in our same little small town up here in Kentucky and we either have the bus pick us up or we drive down to Nashville to meet it.”

The same album also featured the infinitely singable “Speed” and the raucous bar anthem “Hell Yeah.”

“We took (‘Speed’) into Sony and they were like, ‘Nah, you’re not gonna cut that song’ … but we fought for that song and it was a big hit,” Montgomery said. “They were like, ‘Ain’t no radio station ever gonna play ‘Hell Yeah.’ Well, look how big it ends up being, it’s one of our biggest hits. … We sang about the good, the bad, the ugly and the party on the weekend. When you’re making ends meet every day, sometimes you gotta let go of that stress.”

Montgomery Gentry’s fourth album “You Do Your Thing” (2004) kept the hits coming with “If You Ever Stop Loving Me,” “Gone” and the aforementioned platinum hit “Something To Be Proud Of,” which salutes military veterans.

“This is the greatest country in the world,” Montgomery said. “We can say and be and dream as big as we want to in this great country. We just don’t give it up enough for all of our great American heroes. I’m named after my uncle, Edward Montgomery, who was a fifth Marine that got killed on Iwo Jima. We forget our freedoms, especially when you go around to all the other countries, you see why people are dying to get into America, not get out of it.”

Their 2005 “Greatest Hits” compilation included the brand new bonus track “She Don’t Tell Me To,” which was a smash hit ironically as the inverse of “She Couldn’t Change Me.” This time, it was a love song about respecting your wife, not because she tells you to, but because it’s simply the right thing to do.

“I always told the label and T-Roy, ‘Boys, I ain’t singing no damn love song,’ and of course, I ended up writing one about my wife, so there you go,” Montgomery said.

Their fifth album “Some People Change” (2006) had a powerful title track saying, “His old man was a rebel yeller, bad boy to the bone, he’d say: ‘Can’t trust that other fella,’ he’d judge ’em by the tone of their skin. He was raised to think like his Dad, narrow mind full of hate, on the road to nowhere fast, till the grace of God got in the way, then he saw the light and hit his knees, cried and said a prayer, rose up a brand new man, left the old one right there.”

“America is going to work itself out,” Montgomery said. “It’s too free and too great not to be.”

The same album also featured hits like “What Da Ya Think About That” and my favorite “Lucky Man.”

“It’s unreal, that song (‘Lucky Man’),” Montgomery said. “We don’t slow it down much, but when we do, we feel like we’ve got something to say. One of my great buddies wrote that song, and when I heard it, I was like, ‘Man, I gotta cut that song.’ It’s as country as dirt, boy, and I love it. I sing it every day when I get on stage. … I can be at Walmart and people come up and go like, ‘Hell yeah, turn it up,’ or go, ‘I’m a lucky man,’ or ‘This is my town!'”

Their sixth album “Back When I Knew it All” (2008) featured another hit title track, as well the catchy tune “Roll with Me,” while their seventh album “Rebels on the Run” (2011) tore up the radio with “Where I Come From.”

Unfortunately, their eighth album “Folks Like Us” (2015) would be the duo’s last together before Gentry’s untimely death, after which Montgomery paid tribute to his lifelong buddy with “Here’s to You” (2018).

“There’s not a day that goes by that we don’t think of him,” Montgomery said. “He was full of life, he loved living life and he loved people. … He was such a big practical joker and he actually had this gigantic wooden spoon on the bus because he liked stirring stuff up! Of course, I know everybody out there, they don’t have to tell me, he was the pretty one, I get it. … As soon as he’d show that big, beautiful smile of his, everything was fine.”

Today, he vows to carry on Montgomery Gentry’s legacy between occasional gigs with his brother, John Michael.

“Me and T-Roy made a promise … if one of us goes down, we want the other one to keep going,” he said. “When everything is said and done, here’s how we’ll know we done anything at all: If you walk over to a jukebox, you’re gonna see a Merle Haggard song, a Waylon and Willie song, a Bob Seger song, a Lynyrd Skynyrd song, a Charlie Daniels song. If we’re in between them somewhere, we can look at each other and go, ‘We’ve done something.'”

Or, as they sang in their platinum hit: “If all you ever really do is the best you can, well, you did it, man.”

WTOP's Jason Fraley celebrates 25 years of Montgomery Gentry (Part 2)

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Jason Fraley

Hailed by The Washington Post for “his savantlike ability to name every Best Picture winner in history," Jason Fraley began at WTOP as Morning Drive Writer in 2008, film critic in 2011 and Entertainment Editor in 2014, providing daily arts coverage on-air and online.

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