In July 2024, Luke Bryan honored the late Toby Keith with a rendition of Keith’s breakout hit “Should’ve Been a Cowboy.” Taking the stage at Nashville’s Bridgestone Arena, the five-time Entertainer of the Year swapped out his trademark baseball cap for a more traditional black cowboy hat. The gesture went beyond a simple wardrobe change—it was a tribute to Bryan’s late sister, Kelly, who died unexpectedly in 2007. Now, the “Rain Is a Good Thing” crooner is opening up about what caused her death.
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Luke Bryan’s Sister’s Death Was “Tragic Beyond Words”
“I’ve never really explained what happened to my sister,” Luke Bryan said during an appearance this week on All There Is with Anderson Cooper. “You know, there’s some misinformation out there on the Internet.”
Bryan’s older sister, Kelly, was just 39 years old when she died on May 8, 2007. Tragically, Kelly’s husband, Ben Lee Cheshire, suffered a fatal heart attack seven years later in 2014. Bryan and his wife, Caroline, adopted the couple’s three children and raised them as their own.
The American Idol judge explained that his sister was part of “a very, very small percentage of people that die for no reason in the world.” Medical professionals described the cause as “sudden death syndrome.”
“She was in her home doing her laundry and… Anderson, it was like, you know, somebody just turned the switch off on her,” Bryan said. “And… it was just tragic beyond words.”
[RELATED: Luke Bryan Gets Choked up During Toby Keith Tribute, Honors His Late Sister]
On Grief, Loss, and Family
By that time, the Georgia native was no stranger to tragedy. In 1996, as he was preparing to move to Nashville in pursuit of a country music career, Bryan’s older brother, Chris, died in a car accident. He was just 26 years old. Still, this loss felt different.
“She was everything in our lives. She was a mother of three children, and she was, I mean, the best mother you could ever dream of,” Luke Bryan told the CNN anchor. “And we all leaned on her for so many things, and it’s hard to really wrap your brain around. And it was so different than my brother, because my brother, you can conceptualize a car accident, but you can’t really conceptualize someone that was 5’11”, 130 lbs., healthy as a horse—and she’s just gone.”
Despite the seemingly insurmountable grief, the “Drink a Beer” singer didn’t have to look far for silver linings. “Being able to have her children and look into their eyes and see my sister has been a much more helpful process,” he said. “I can see her in them. I can see mannerisms in them, I can see so many tangible things.”
Featured image by Jason Kempin/Getty Images for ACM








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