His father is a former basketball star who set scoring records at the University of Missouri and was drafted by the Cleveland Cavaliers.

He was also the basketball coach, biology teacher, and assistant principal at Kennett High School.

In his junior year of high school, Tomlinson reached the finals for "You Can Be a Star," a television talent show on The Nashville Network (now Spike TV), in which Trent placed second.

Two additional singles were also released from the album: "One Wing in the Fire" and "Just Might Have Her Radio On," the former is a song about Tomlinson's father.

On December 15, 2008, it was announced that Tomlinson would be the second artist signed to Lyric Street's subsidiary label, Carolwood Records.

A third single, "Angels Like Her" (a re-recording of a song on his debut), was released on October 26, 2009, shortly before the closure of Carolwood.