[5] Music has been an important aspect of his family for several generations, especially on his mother's side: his great-grandmother, Kitty Cora Cline, was one of the first female members of the Grand Ole Opry; her daughter, Gladys Cline Graves, wrote songs and poetry, but did not pursue a career, as she had eleven children and chose to focus on raising them instead.
He won several talent shows during grade school, and when he was eleven years old, he performed the National Anthem at a Vanderbilt University basketball game.
[4][6] In second grade, Briley was inspired by the devotion that he felt for his younger sister, Mary Meggan, to request that his school observe a special holiday for siblings.
[4] His primary musical influence is Johnny Cash, and his style encompasses a wide variety of genres, including country, gospel, bluegrass, southern rock, R&B, and blues.
He continued to pursue music during college, performing with multiple bands in coffee houses and joining a gospel group called "25 Drive".
[15][16] Holly Tong wrote in the Lebanon Democrat that Outlier "showcases [Briley's] individuality and versatility".