A willingness to take less attractive roles has earned blond, athletic Big strong character parts like the misguided bully or the sympathetic class clown in lieu of the romantic lead, setting him apart from the pack of young heartthrobs. The Minnesota native moved to Los Angeles following his high school graduation and after a talent search ended with a failed audition for the Abcsoap "All My Children", Scott landed a guest stint on The WB's sitcom "Unhappily Ever After" in 1997. That same year he made his TV-movie debut with a supporting role in the NBC fact-based drama "Born Into Exile" and was featured the following year in an episode of the Abcsitcom "Something So Right".

Although he was in his twenties, Scott possessed youthful looks that allowed him to be cast convincingly in teen roles, a definite asset to the up and comer while the industry was in the midst of a millennial teen film boom. In 1999, Scott made his big screen debut with a breakthrough role in the popular teen sex comedy "American Pie". He played Stifler, a crass, loutish senior whose luck with the ladies and constant taunting of his less fortunate peers leads the group to resolve to lose their virginity before graduation. He excelled as the bad guy, playing the despicable part with aplomb, skillfully handling his character's overconfidence and the appropriately graceless ways he reacted to his comeuppance. The next year Scott returned to the big screen with an engaging portrayal of class clown Billy Hitchcock in the high school-set thriller "Final Destination". Narrowly escaping a plane crash, Hitchcock and his fellow survivors find that death isn't accepting this change of plans without a fight, and the actor brought a much-needed comic relief to the harrowing events. Here Scott proved a charming screen presence, with a sweetly awkward role much more likable than his "American Pie" character. He followed up that same year with a co-starring turn as one of a group of college guys from Ithaca, New York who accompany a friend (Breckin Meyer on a "Road Trip" (2000) to Texas in an attempt to retrieve an explicit and incriminating videotape before it falls into the wrong hands.