It was a true celebration at the Grand Ole Opry on Wednesday, Jan. 9, as multiple generations of country music united to pay homage to their friend, the late Troy Gentry of the duo Montgomery Gentry, at the C’Ya on the Flip Side tribute concert.
The Opry house was filled to capacity with fans–or as Montgomery Gentry calls them, friends–who dedicated their time to honor the memory of Gentry, who was tragically killed in a helicopter crash in 2017. An expansive lineup that featured co-hosts Blake Shelton and Storme Warren, Dierks Bentley, Rascal Flatts, Chris Janson, Jimmie Allenand Dustin Lynch all entertained the loyal crowd with the hits that made Montgomery Gentry one of the genre’s iconic acts.
The event honored Gentry’s legacy not only in music, but in service. The inaugural concert served as a fundraising event for the Troy Gentry Foundation instituted by his wife Angie Gentry, benefiting causes they’ve long harbored a passion for including the TJ Martell Foundation, Make-A-Wish Foundation and the Journey Home Project. “Behind that smile was a huge loving heart and he loved to give to other people,” Angie said glowingly of her late husband. “He was very humble, and I think this would have floored him, all of the outpouring and emotional support and the people that called and wanted to be a part of it.”
In addition to covering their favorite Montgomery Gentry songs, the artists also dedicated their own numbers to Gentry’s memory. After an honorable rendition of “Drink Along Song,” Bentley delivered a moving performance of “I Hold On,” bringing new meaning to the lyrics. “When I did my very first motorcycle Miles & Music events, they were the first ones to say yes to that,” Bentley said of the duo’s participation in his charity ride. “And Troy, he rode with me every year. For 10 years, he had his bike out there on a Sunday, giving up time at home to be there to help raise money for the Vanderbilt Children’s Hospital.”
One of the most stirring moments of the show came when Shelton offered a poignant reflection of his 17-year friendship with Gentry, looking back on the joyful moments and hardships they endured. “He was literally like a family member to me,” Shelton described. “He was one of my heroes.” He followed the sentiment with a haunting performance of “Over You,” the CMA Award-winning song he wrote with Miranda Lambert about his late brother, recalling the sincere impact the song had on Gentry.
Allen is another artist who knew what it meant to have Gentry as a close friend. The burgeoning star, who brought the audience to its feet with a lively cover of “Hell Yeah,” shared how he met his future mentor at the gym in 2008. Upon learning about Allen’s musical aspirations, Gentry offered him his phone number, and they remained friends that day onward. “He told me, ‘man, just stay true to who you are as a person, who you are as a musician. Eventually, you’ll find your way…it’s about your moral beliefs and who you are as a person,’” Allen recounted of Gentry’s words of advice and belief in him as an artist. “That really helped me, my confidence, for a long time.”
Brice offered another one of the evening’s powerful moments with “I Drive Your Truck.” He was inspired to perform the moving song about losing a loved one by an event that occurred in the days following Gentry’s passing, when a group of his friends took his black Camaro on a joy ride to one of his favorite bars. “Everything about Troy is something to look up to,” Brice reflected. “He was humble, but he was also fun and funny. Life is so short, obviously, and he made the most of it. We all wanna try to be like that.”
The evening came to a somber, yet celebratory close when Montgomery silently walked on to the stage, kissing Gentry’s guitar before placing it in the legendary Opry circle with a single spotlight shining on it. As Gentry’s personal triumph song “Better Me” played in the background, a slideshow of his life unfolded through personal photos with family, friends and on stage alongside his longtime music partner.
“I just wanna keep his legacy alive here, man, and make sure it stays alive in Nashville, and I’m gonna make sure it stays alive on the road,” Montgomery vowed. When he returned to the stage, Montgomery was joined by all of the performers for an all-star sing-along of one of the duo’s defining hits, “My Town.” It was a moment that not only honored the Montgomery Gentry legacy, but Gentry’s timeless spirit, which could be felt in the hallowed Opry house filled with pure musicianship and the fulfilling friendships he spent his life surrounded by.