Music has always been an important part of Wiley’s life. Wiley's great-grandfather played guitar and performed in juke joints in Alabama. Wiley’s grandfather, along with his grandfather’s brothers, sang together as a group, and performed for church congregations throughout Alabama. Wiley’s cousin, the late Avery Richardson, was a gifted singer and is an inductee in the Alabama Jazz Hall of Fame. Wiley began playing the piano at the age of five, and had his first recital at the age of six. Although Wiley enjoyed playing the piano, there was always a constant “tugging” at his heart to sing. After being baptized in 1994, and joining the church choir, Wiley soon realized that God had gifted him with the ability to sing. It was then that he finally realized the “something special” God had planned for him. In 2004, Wiley's recording, On My Knees, made the 46th Grammy Entry List in the category of Best Male Pop Vocal Performance.