In July, 2006, Troy Gentry was lounging shirtless near a wading pool outside Montgomery Gentry’s bus in Fort Loramie, Ohio, soaking up some sun before the duo hit the stage that night at Country Concert.
Nearby were two signs tacked to a fence: “Do Not Cross This Fence” and “This Means You, Troy.” The second sign had a figure on horseback with a slash through it, a reminder of the band’s previous trip to Fort Loramie, when Gentry hopped on a horse for a ride after a few drinks. The ride ended badly when Gentry’s horse reared and sent man and horse rolling down a hill. Gentry broke an ankle and tore knee ligaments.
But that was Troy Gentry. He was always up for an adventure. One day, he would run around in his Batman costume and tell anyone who would listen: “I’m Batman.” The next he might goof off with his daughter, Kaylee, or raise a glass at a campsite with fans. He carried around a wooden spoon because he was always stirring stuff up, his longtime pal Eddie Montgomery says.
So, it was not surprising when Gentry, 50, accepted the offer of a helicopter ride before the band’s show in New Jersey on Sept. 8. It was just another adventure for the Lexington, Ky., native. But the helicopter encountered engine problems and crashed, killing Gentry and the pilot, James Robinson.
“I feel his presence all the time,” Montgomery said last week in an interview with The Blade. “If you ever met T-Roy, you never forgot him. He always had that big smile.”
For almost 35 years, the two men were nearly inseparable. Both grew up in the honky-tonks of Kentucky. Montgomery was playing drums in his parents’ band at the age of 13. He later formed the Lexington band Early Tymz with his younger brother, John Michael Montgomery, and the local kid, Troy Gentry.
“When I first met him, my thought was, ‘What a pretty boy.’ He just had that GQ look,” Montgomery said, chuckling. “I told him, ‘You look pretty, but can you sing?’”
Their on and offstage antics became legendary around Lexington. And, they were a breath of fresh air when they broke through in Nashville with their 1999 debut single, “Hillbilly Shoes.” Their post-show parties on their bus became a challenge for fans to figure out how to get to, and many of them figured it out. It was not unusual for more than 50 people to cram aboard the bus. Montgomery and Gentry never called them fans. They were “friends.”
“There are some videos out there that I hope never surface,” Montgomery said with a hearty laugh. “We had some wild times. You hear about those guys at the end of their life who say, ‘I wish I had tried that.’ For me, it will be, ‘Maybe I shouldn’t have tried that.’”
Two days before the accident, Gentry and Montgomery wrapped the production of the band’s newest album, Here’s to You. It was originally envisioned as a 20th anniversary celebration of the breakthrough of the southern rock-influenced Montgomery Gentry. But Gentry’s death jeopardized the project and sent Montgomery into an emotional tailspin.
On Sept. 14, Nashville came together to remember Gentry at an emotional memorial at the Grand Ole Opry. It was a who’s-who of Music City. Vince Gill, Charlie Daniels, Travis Tritt, Trace Adkins, Little Big Town, and others eulogized Gentry or performed.
“We have the fondest memories of Troy,” Karen Fairchild of Little Big Town said. LBT and Montgomery Gentry became close during a 2010 tour. Gentry’s big smile, graciousness, and zest for life left an impact on Fairchild. “It is such a tragic loss for the country music family. I can’t imagine the pain of losing a band mate, a partner. Troy was a special man.”
For Montgomery, the pain was numbing. The days after the accident were a blur. The last thing on his mind was the album.
“I mean, everything hit me like a ton of bricks. I didn’t know where I was at. But then the label began asking me about the CD. I was asking myself: ‘Do I keep touring? Do I put the CD out?’”
When Montgomery finally got away from the well-wishers and the never-ending news cycle about the accident, he remembered a late-night conversation with his friend that they had years ago over a few drinks.
“We agreed that if anything ever happened to us, that we wanted the other person to keep the Montgomery Gentry brand going,” Montgomery said.
So he has. Montgomery Gentry has opened a few shows for Alabama. Longer gigs, including a return to Fort Loramie in July, are going to follow. Here’s to You was released on Feb. 2 — now a celebration and a tribute.
Montgomery said he believes that the album has the best vocals of Gentry’s career. It reminds him of the duo’s debut album, Tattoos & Scars. It is hard-charging, at times patriotic, and faithful to the Montgomery Gentry sound. “Drink Along Song” was a festival favorite in the summer, even before it was recorded. The catchiness and attitude of “Shotgun Wedding” and “What’cha Say We Don’t” will appeal to longtime fans.
But, for Montgomery, one song will always be Gentry’s.
“There have been songs over the years where I can hear T-Roy singing it or he can envision me singing it. When we got ahold of ‘Better Me,’ he said: ‘Man, I really want to sing that song.’”
The lyrics captured Gentry’s emotional journey from wild man to family man:
“I might cuss and fight, tell a few lies/Break a few rules, making promises I can’t keep/But I’ve turned the page on wilder days/I’m writing all this down hoping you’ll see/I ain’t saying I’m perfect, but I’m working on a better me.”
“It’s the man he ended up being. He was a great father to Kaylee and a husband to Angie,” Montgomery said. “He taught me to be a better dad.”
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