To finance tuition at his private high school, Strait worked as a model for such top photographers as Bruce Weber, Herb Ritts, Steven Klein, and Tony Duran while pursuing theatre roles.

Born and raised in Greenwich Village, Strait was planning a move to Southern California to pursue film work, when he was cast in Sky High. While in Los Angeles with the sole objective of finding an apartment, Strait’s agent insisted he go on just one audition. Sky High marked Strait's first film role. Strait is also the lyricist and lead singer for the band Tribe.