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In 1995, during his junior year of high school, Bass received a call from Justin Timberlake and his mother, Lynn Harless, who asked Bass if he would be interested in auditioning for the pop group NSYNC after the group's original bass singer, Jason Galasso, had quit.

According to an episode of VH1's Driven, Jan Boltz, president of BMG's German division, offered NSYNC a recording contract under the condition that they replace Bass, whose dancing, he felt, "wasn't at the same level as all the others." The group's first single, "I Want You Back" began receiving major radio play in the United States, and NSYNC soon found themselves becoming an "overnight sensation", a period which Bass describes in his autobiography as "the death of my own innocence".

The film also featured a soundtrack which included previously unreleased songs by NSYNC and Britney Spears.

Bass collaborated with Joey Fatone, Mandy Moore, Christian Burns and True Vibe (as the "On The Line Allstars") for the film's theme song, "On The Line".

NSYNC's success led Bass to work in film and television.