Damian has released five albums with eight top 40 hits, including his number-one cover of the David Essex song "Rock On" (from the Dream a Little Dream soundtrack), which was certified gold in 1989. He also won a BMI Song-writing Award for his hit single "Was It Nothing at All". He made his feature film directorial debut with an indie comedy, Hot Tamale, which he co-wrote with his wife Janeen, who is the daughter of actor James Best. Following in the family film genre, he directed the films Moondance Alexander, Flicka 2, Marley & Me: The Puppy Years, Flicka: Country Pride, and A Princess for Christmas. In 2012, he directed and co-wrote, again with his wife, the 90-minute romantic comedy The Sweeter Side of Life. The film premiered on the Hallmark Channel on January 19, 2012.