Luke Bryan Opens up About His Late Brother, Sister and Brother-in-Law 'Guardian Angels'

Luke Bryan is one of the biggest country stars of his generation, overcoming a series of personal tragedies along the way. "I've had so many tragedies in my life," he told PEOPLE, "it's almost like you don't want to tell the story because you don't want to feel like you're out there craving sympathy."

In 1996, Bryan's older brother, Chris, was killed in a car crash at age 26, and in 2007, his older sister, Kelly, died suddenly from natural causes that are still unexplained. In 2014, her husband, Ben Lee Cheshire, died of a heart attack, and Bryan and his wife Caroline took in Kelly and Ben's three children, Jordan, Kris and Til. "You truly never get over it," Bryan said of the loss he has experienced. "You truly never settle in your mind that it's happened. I mean, it's always there."

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Bryan now considers Chris, Kelly and Lee his guardian angels and feels a "deep connection" to them. "Maybe Chris and Kelly and Lee have moved some puzzle pieces around to make my life so fortunate," he said. "When I say my prayers at night, I have to say, 'Thank y'all for looking after us down here.'"

The singer's personal tragedies are part of the story of his upcoming docuseries Luke Bryan: My Dirt Road Diary, a five-part IMDb TV Original docuseries that will begin streaming on Aug. 6. "If I can inspire people to move on from tragedy, hopefully by my behavior," he reflected, "that's what life's all about for me."

The docuseries was directed by Michael Monaco and will include original home videos, interviews and personal footage and is expected to air this summer. Bryan shared during a visit to The Ellen DeGeneres Show earlier this year that Monaco "was capturing my life." "And there's A) the challenges of trying to navigate the music business," he said. "But then the challenges of all of the loss of some of my siblings and my family members."

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The Georgia native added that he and his team "felt like, 'Let's put this thing out.' ... It's been a tough year for everybody and if people see my challenges and the things I've kind of had to go through in life, maybe it'll inspire some people, certainly in these times, to dust themselves off and keep rocking," he said, adding, "I tell people, if you've lived this life long enough, life's gonna get you. You can't be living this long, beautiful life without some ups and downs and challenges. And we've certainly had those. I think this documentary really shows the struggles and stuff that you have to deal with from time to time."