Jordan Runtagh
November 15, 2017 01:30 PM

Years ago, Troy Gentry and Eddie Montgomery had a difficult discussion: what to do if the other died first. More than just buddies, their musical bond forged the hit-making country duo Montgomery Gentry. They had a musical legacy to protect and fans to consider. “We said to each other, ‘Hey, we want Montgomery Gentry to keep going,’” Montgomery says. “It’s weird, I always thought it was going to be me that went down first.”

His premonition was not to be. On Sept. 8, hours before they were due onstage at the Flying W Airport and Resort in Medford, New Jersey, Gentry opted to board one of the venue’s helicopters for a preshow joyride. “They texted us about a week before saying, ‘We have helicopter rides!’ We wanted to do it,” Montgomery remembers. Minutes after takeoff, the two-seater craft became crippled by engine problems. It tumbled out of the sky just before 1 p.m., crashing into a wooded area short of the runway. Pilot James Evan Robinson was killed on impact, but the gravely injured Gentry was rushed to nearby Virtua Marlton hospital. He died later that day at age 50, with his friend of 30 years by his side.

“A little piece of my soul got lost there,” Montgomery, 54, tells PEOPLE exclusively in this week’s issue. “It was a horrific day; my world changed as much as the band did. It’s something that you never get over. It’s going to be in my mind and my soul for the rest of my life.”

Wreckage from the helicopter crash that killed Troy Gentry and pilot James Evan Robinson
COURTESY NBC10 News Philadelphia

It was the tragic end of a partnership that began decades earlier in the honky-tonk clubs of Kentucky. “Me and T, we’ve known each other longer than we’ve known our wives,” he says. “Nashville didn’t put this duo together, we did. We were friends before we were ever in the music business.” The pair began playing together alongside Montgomery’s brother John Michael. Today, Montgomery laughs at his first impressions of his future partner: “I thought he was a pretty boy and he could sing.”

Montgomery Gentry perform in the early '90s
Courtesy Montgomery Gentry

After briefly pursuing solo ventures, they joined voices — and names — in 1999, scoring No. 1 smashes like “My Town,” “Hillbilly Shoes” and “Something to Be Proud Of.” Even when they weren’t sharing a stage, they often spent time together.

“We were outdoors guys. We’d hunt and fish. Mostly we’d go around and listen to a lot of bands and think how we could make ourselves better.” Mischief was regularly on the agenda. “There’s a lot of things that went on after 1 a.m. that I can’t talk about,” he says with a chuckle.

Troy Gentry and Eddie Montgomery
Kristin Barlowe

Gentry brought his wicked sense of humor on tour. Even in the middle of a concert, he couldn’t resist cracking a joke on the talkback mic, reducing the group to helpless hysterics.

“He’d say something that would be plum off the wall. You had to just stop and laugh your ass off. I know damn well that everybody was out there going, ‘What in the world are they laughing about?’” The singer also displayed a penchant for dressing up as his favorite super hero. “Troy was a Batman nut!” Montgomery recalls. “He’d walk around and mess with people.”

Troy Gentry
Ed Rode/AP

For more on how Eddie Montgomery is moving forward after the loss of his longtime musical partner Troy Gentry, pick up the latest issue of PEOPLE, on newsstands Friday.

Days before the crash, Montgomery Gentry were in the studio, putting final touches on their new album Here’s to You, due out Feb. 2. One song, “Better Me,” touched them both. The lyrics depict a man whose youthful fire is starting to dim. The opening lines, sung by Gentry, would take on an eerie prescience given what fate had in store. I’m getting older, finding myself and God getting a little bit closer. “It’s probably the best I’ve heard him sing,” Montgomery says proudly. It was released as a single just after Gentry’s death — a musical eulogy.

Montgomery credits his wife, Jennifer, and colleagues in the country music community with helping him cope with his grief.

“We never called anyone fans — we called them friends,” he tells PEOPLE. “And me and Troy have been blessed over the years to have a lot of friends.” On Sept. 14, 1,500 these friends gathered at the Grand Ole Opry to remember Gentry. The star-studded memorial service included performances by Trace Adkins, Charlie Daniels, Little Big Town and a stirring speech from Vince Gill. “He told me: ‘Man, don’t shut down on us. The best way to keep Troy alive is to keep going.’”

RELATED VIDEO: Troy Gentry’s Eulogy Delivered at the Grand Ole Opry

He plans to do just that. On Nov. 8, Montgomery made a surprise appearance at the 2017 CMAs, where he performed “My Town” alongside Dierks Bentley and Rascal Flatts. In late January, he hopes to head out on tour and share the songs he and Gentry loved so much.

“I’ve never done anything else but play music,” he says of moving forward. “It’s all I’ve ever known.” Even though Gentry’s place on the stage will now stand empty, Montgomery says he’ll carry the memory of his friend with him each night. “He was more than just a singer. He was a brother and he was always there. As far as I’m concerned, we’re still making music together.”

Montgomery Gentry’s Here’s to You Tour Dates:

January 19 – Sioux Falls, SD at Denny Sanford Premier Center (with Alabama)
January 20 – St. Charles, MO at The Family Arena (with Alabama)
February 9 – Columbia, MO at The Blue Note
February 10 – Springfield, IL at Boondocks
February 23 – Indianapolis, IN at 8 Seconds Saloon
March 2 – Clifton Park, NY at Upstate Concert Hall
March 3 – Lynchburg, VA at Phase 2
March 9 – Jordan, NY at Kegs Canalside
March 10 – Warrendale, PA at Jergel’s
March 16 – Medina, OH at Thirsty Cowboy
March 17 – Columbus, OH at The Bluestone
March 22 – Augusta, GA at Country Club Dance Hall and Saloon
March 23 – Birmingham, AL at Iron City
June 2 – Marion, KS at Chingawassa Days Festival
July 6 – Ft. Loramie, OH at Country Concert at Hickory Hill Lakes
July 13 – New Salem, ND at ND Country Fest
July 14 – Pierz, MN at Pierz Freedom Fest
July 20 – Hillsboro, MO at Jefferson County Fair
July 21 – Springville, IN at The Boogie
July 27 – Ridgefield, CT at Ridgefield Playhouse
July 28 – Bar Harbor, ME at Criterion Theater
August 2 – West Allis, WI at Wisconsin State Fair
August 17 – Zanesville, OH at Muskingum County Fair
September 8 – Manistee, MI at Little River Casino
September 15 – Ventura, CA at Boots and Brews

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