In 2001 the young actor scored his first feature starring role, playing half of a brother-sister team who stumble upon a mysterious horror than feeds on humans in the eerie thriller "Jeepers Creepers"—Long would also be spotted in an uncredited cameo in the 2003 sequel. Somewhat lighter was "Happy Campers," a teen comedy set at a summer camp in the midst of anarchy that screened at Sundance 2001. He followed with a brief but hilarious co-starring turn opposite teen diva Britney Spears in the drama "Crossroads" (2002). Although he had long since perfected the role of awkward, nerdy teen, Long offered up a fresh variation when he appeared as the catcher-cum-cheerleader Justin, hoping to impress his dream girl, in the sports comedy "Dodge Ball" (2004).

For his next role, he played a friendly mechanic who rebuilds the famed animated Volkswagen Bug in the G-rated Disney sequel-cum-remake, “Herbie: Fully Loaded” (2005). In the low-budget comedy “Waiting” (2005), he played a waiter who suddenly beings to fret over his dead-end life after learning about an old high school classmate making good with a lucrative engineering career.