Dec. 14, 2021, would have been Troy Gentry's 22nd wedding anniversary. Gentry, one-half of the award-winning duo Montgomery Gentry, wed Angie McClure on Dec. 14, 1999, in Maui, Hawaii.

Gentry and McClure's union came just as Gentry's career was taking off: Montgomery Gentry's freshman album, Tattoos & Scars, was released the same year. The record's first three singles, "Hillbilly Shoes," "Lonely and Gone" and "Daddy Won't Sell the Farm," each landed in the Top 20. Gentry received a belated wedding gift thanks to the project as well: The duo's album was certified platinum, for sales of one million copies, three months after he tied the knot.

In 2002, the Gentrys welcomed daughter Kaylee into the world, which Troy Gentry said made him, and their family, stronger.

"I've grown up," he once told Nashville Parent magazine. "I’m more responsible now. Before children, the social scene was more important to me. Now, I’d rather be home with my family than out all night. Angie and I have date nights, of course. But I travel a lot for work, so I find comfort here at home."

The Gentrys' marriage was tested in 2014, when Angie was diagnosed with breast cancer. Her illness inspired Montgomery Gentry to launch the Check Your Headlights campaign for breast cancer awareness.

"As you know, we launched this 'Check Your Headlights' campaign for breast cancer awareness in early October," Gentry shared on his Facebook page at the time. "What you didn't know is that right before we launched, my beautiful Angie got a diagnosis from her doctor that has rocked our world a bit over the last few weeks. She has breast cancer -- and we wanted you to hear it from us first. She is currently going through chemo treatments, and her prognosis is very good. We’d love for you to keep her in your prayers over the next few months."

Thankfully, Angie's cancer was caught early, but Gentry admitted that it was a lot to handle.

“It’s devastating just to hear the word cancer,” he told The Boot, “but with today’s technologies, medicines, all that, and having the support of people who have defeated cancer, it’s great to have in your corner."

Sadly, three years later, Gentry died in a helicopter crash on Sept. 8, ahead of a Montgomery Gentry show in New Jersey. In February of 2018, Angie filed a wrongful death lawsuit against the manufacturers of the aircraft.

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