On Wednesday, Jan. 9, the foundation hosted a star-studded C-Ya On The Flipside benefit concert at the Grand Ole Opry in Nashville, with some of Music City's biggest stars coming together to help raise money for the foundation as well as organizations including the TJ Martell Foundation and The Journey Home Project, causes that Gentry's family has long supported.
"He just wanted to help people and he wanted to have fun doing it," Angie said backstage of her husband. "It was things that were personal that mattered to him, that touched his heart, that touched our families, touched both of us."
The event was hosted by Blake Shelton and Storme Warren, with The Voice coach remembering Gentry as he and Warren made their first appearance on stage.
"I don't know that I ever saw him without a smile on his face, and a cup in his hand," Shelton told the crowd. "He loved life, and he was one of my heroes."
"He's the reason that I turned out like I did," he added, with Warren jokingly chiming in, "Explains a lot, doesn't it folks?"
Before the curtain rose on the concert, the theme from The Dark Knight could be heard playing over the speakers, the choice of music paying homage to Gentry's love of Batman. Warren and performer Jimmie Allen also made a nod to the character, wearing Batman t-shirts in honor of Gentry.
"T-Roy was just a big kid," Ira Dean said backstage when asked about his friend's love of Batman. "He was just into Batman and I think he liked just being a big kid. If it could have been Halloween every day, he'd love it."
Jon Pardi opened the show with a rendition of one of Mongtomery Gentry's first hits, "Hillbilly Shoes," followed by Dustin Lynch, Chris Janson and Darryl Worley, who performed his song "Second Wind" to an emotional audience.
Worley explained backstage that he had been playing "I Miss My Friend" at his shows in tribute to Gentry, but this time, he got a nudge to do something different.
"I prayed about this, because in a situation like this, you want to do the right thing," he said. "And it was almost like I heard [Gentry] say, 'Hey, you know what? I'm OK. It's good over here. But I've still got family and loved ones back there that are struggling. So don't do a song for me tonight. Do a song for them.'"
While Worley's performance marked one of multiple poignant moments throughout the night, the show was meant to be a celebration, with the audience happily obliging as they cheered, stood up and even exchanged some banter with the artists on stage.
Other performers on the nearly 20-strong lineup included Dierks Bentley, Rascal Flatts, Lee Brice and Shelton, who surprised the crowd with a rendition of "Over You," a song he wrote for his late brother. Gentry's bandmate, Eddie Montgomery, closed the show with Montgomery Gentry's "My Town," calling the night "unbelievable" backstage.
"If T-Roy was here, he'd be smiling his butt off," he said. "Man, he'd be right in the middle of it. If you ever got around him and seen that smile, you never forget it."
Photo Credit: Getty / Jason Kempin