Trousdale began his Broadway career when he was eight years old, touring with the production of Les Misérables, where he starred alongside Ashley Tisdale. He was later cast as Friedrich von Trapp in the 1998 Broadway revival of The Sound of Music. After a successful run, he moved to New York City at the age of ten, to join the Broadway production of the play with Ricky Martin and Lea Michele of Glee. While in New York, he joined the well known children’s group The Broadway Kids (past members include Christy Carlson Romano, Jenna Ushkowitz, Gregory Raposo, and Lacey Chabert) and performed in popular plays such as Beauty and the Beast (musical), The Wizard of Oz (1987 musical), and the Radio City Christmas Spectacular.

When he was 14 years old, Trousdale caught the attention of two producers who were putting together a boy band in New York City. Consisting of five members, including former Sugar Beats member Jesse McCartney and former Broadway Kids bandmate Greg Raposo, he joined Dream Street in 1999. Chris Trousdale met Greg Raposo during their time in The Broadway Kids. They were later reunited for Dream Street. Dream Street released their debut album Dream Street (Dream Street album) in 2000. They released their finale album “The Biggest Fan” in 2002. After releasing The Biggest Fan Dream Street broke up.

Trousdale went on to record “Kissless Christmas” and “Wild Christmas” for School’s Out! Christmas album in addition to the popular duets with the girl group Play (rendition of “I’m Gonna Make You Love Me”) and solo artist Nikki Cleary (remake of the Grease track “You’re the One That I Want”), which were huge hits on Radio Disney. However, shortly after his solo career started to take off, Trousdale put his career on hold in 2006 and moved back home to Michigan to take care of his ailing mother.

On June 30, 2014, Trousdale announced via Twitter that he had joined the Spectra Music Group to work on his solo album.

On June 2, 2020, Trousdale died at a hospital in Burbank, California, at the age of 34 due to complications from Covid-19.

On June 11, 2020, what would have been his 35th birthday, his former Dream Street bandmates reunited online for a virtual acoustic performance of their hit song “It Happens Every Time” in Trousdale’s memory.