At 18, a friend asked Billings to play one of his songs and sing at his wedding, and he reluctantly agreed.

In 1998, with the encouragement of family and friends, Billings produced and recorded a demo cassette titled The Further I Go, The More I See.

He signed a single song publishing deal with Ralph D. Johnson of Wedge Records.

On October 12, 2009, "21 GUNS (Fallen Soldier Song)" debuted on the TOP 20 on Demand chart on Clear Channel Communications.

The song appeared on the Independent Music Network's Mainstream Chart on December 9, 2009 and stayed in the Top 30 for over four months.