His second feature-film performance was a major role in the 2000 film Coyote Ugly. Later in 2000, he played the role of Sean in Bootmen. In 2003, he voiced the title character in the film Kangaroo Jack. In 2004, he also played alongside Lindsay Lohan and Megan Fox in Confessions of a Teenage Drama Queen, as the character Stu Wolff, a drunk rock star, who is part of the band Sidarther and is, in Lola's words, "a greater poet than Shakespeare".