Luke Bryan has had immense success with his career, but he's also had his share of tragedy throughout his journey to fame.

In 2000, just as he was about to leave his home in rural Lessburg, Georgia to pursue his dreams in Nashville, his older brother, Chris, was unexpectedly killed in a car accident.

Bryan, the youngest of three children, put his aspirations aside so he could stay home and support his family after their loss. He went to college, worked on his father's farm, and sang at bars at night.

His father, Tommy, knew that Bryan's sense of duty forced him to stick around and the only way to get him to finally work on his musical career was to fire him.

"I said, 'You know, if you're going to pursue your music career, you need to pack your truck up and move to Nashville,'" Tommy told 20/20.

Seven years later, Bryan started to find his footing in the music industry and was even invited to perform at the Grand Ole Opry. His sister, Kelly, gathered over 120 people from Bryan's hometown to attend his Opry debut.

A few days later, she suddenly died in her home and the cause was never determined.

"Just when we started picking up the pieces with my brother, then my sister "” we lose my sister," said Bryan in an interview with Good Morning America.

Just when the Bryans started to catch a break, they were struck with another tragedy. In 2014, Kelly's widower, Ben, died leaving behind their three children.

Bryan's sense of duty once again came into play, and he stepped up to the plate in a major way. He and his wife, Caroline, took in his sister's kids.

Now, in a new candid interview with Robin Roberts, Bryan is opening up about overcoming loss and what it is like to raise his nieces and a nephew.

Bryan, 41, has previously been silent about his many losses, but in the last few years he hasn't shied away from talking about it.

The That's My Kind of Night singer and his wife are now the guardians of his late sister's children, 15-year-old Til and his college-aged sisters, Jordan and Kris.

"We never thought twice about it," Caroline told Roberts. "You know, it was never something that he and I had to sit down and talk about. "˜Should we take this on?' We just did that."

Bryan admitted that it took him a while to get used to raising a teenager, but it got easier as time passed.

"We're buddies now, though, kinda," Bryan joked. "Until he makes me ... that's when I get onto him, I'm like, 'Alright, you're making me be an adult, don't make me be an adult!'"

Bryan also told Roberts that pain of losing his siblings and brother-in-law is something he will always carry with him.

"I've watched my family go through ebbs and flows where we get mad at God and we get mad at why this happened," said the singer.

He then admitted that faith, love and music played big roles in helping him cope with the tragedies.

"Me and my family have gotten together and celebrated and cried over winning entertainer of the year," he explained. "It certainly makes it special when we're all together and we know that people are smiling down, and they're, they're with us, celebrating these amazing moments ... music has certainly helped us through this old, this old crazy ride of life."

"Well, you keep going and you try to, try to be as positive as you can, and you try to appreciate every day," he added. "You'll never get back to 100 percent. You'll always be working to get back to 75 percent."

Did you know about Bryan's story?