A small role in the film "Gattaca" (1997) marked the actor's feature debut, well-cast as the younger incarnation of Loren Dean's lawman character. Scott's enviable onscreen presence helped him make the most of smaller supporting roles, shining in his subsequent two big screen outings. He was featured in Don Roos' acclaimed "The Opposite of Sex", and the New York-raised actor did a fine job of recreating a decidedly Southern twang as Randy, the hometown boyfriend of manipulative DeDee (Christina Ricci). He continued his big screen ascent with a supporting role in the sleeper "October Sky" (1999). In this 1950s-set story based on NASA scientist Homer Hickman's autobiographical book "Rocket Boys", Scott played Roy Lee Cook, the physically abused resident charmer of a group of teenagers joined by their collective interest in space travel and their drive to break free of their oppressive small mining town life. While James Toback's "Black and White" proved a feature misfire, the improvisation-heavy performance offered the actor a unique challenge and a chance to showcase his developing talents with his role as a young man obsessed with black culture who ends up on the wrong side of the law although his estranged father is a Manhattan district attorney.

Scott's notoriously candid interviews and scathing comments about former co-workers from Oprah Winfrey to Claudia Schiffer certainly wouldn't land him a position as a diplomat and might have been expected to hurt his career, but following his incendiary statements, he managed to land sought-after roles in the anticipated Dominic Sena remake "Gone in 60 Seconds" (2000) and Michael Bay's World War II epic "Pearl Harbor" (lensed 2000) which promised to raise his profile considerably.