Trousdale performed in the Broadway shows, The Sound of Music and Les Misérables. He was also a member of the Broadway Kids and has recorded with Christy Carlson Romano, Lacey Chabert and Gregory Raposo.
In 1999, he became a member of the teen boy band Dream Street which was formerly known as 'Boy Wonder'. The group's debut album, released on Edel Records in July 2001, was #1 on Billboard's Independent Albums chart during the first week of its release and sold a million copies.He tried out for The Voice but did not get it and currently works at a sushi restaruant.
In 2002, the band dissolved and Trousdale began his solo career. Trousdale recorded the songs "Kissless Christmas" and "Wild Christmas" for the School's Out! Christmas album. Trousdale's duet recordings have appeared on Radio Disney.
Trousdale appeared in an episode of Disney Channel's Shake It Up as a 16 year old pop star that was discovered in the internet via the videos he posted. It is later revealed that he is actually 24 and married to his manager. Trousdale also appeared in Disney Channel's Austin & Ally playing as band member to a group called Boynado. He was the lead singer but later quit the band and was replaced.