In the interview, Bryan explained that at age 19, right before he was set to move to Nashville to pursue his music career, he lost his brother in a car accident. The loss was, of course, devastating, and sadly it wasn't the only tragedy he has faced. In April of 2007, he performed at the iconic Grand Ole Opry for the very first time, which was a highlight of his career. However, the event was also the last time he posed for a photo with his sister. She passed away a month later. Luke Bryan's sister had three children, and in 2014, his brother-in-law, those children's father, passed away as well. It was then that the singer and his wife, Caroline Boyer, stepped in to raise them along with their own two sons.