After completing "Scream 2", Gayheart was cast in a lead role in the slasher film "Urban Legend" (1998), in which she portrayed the best friend of a college student (Alicia Witt) who suspects their friends are being murdered according to urban legends. The same year, she appeared onstage at Toronto's Canon Theatre in a production of "The Last Night of Ballyhoo", opposite Rhea Perlman and Perrey Reeves. In 1999, Gayheart also starred in the black comedy film "Jawbreaker" with Rose McGowan, Julie Benz, and Judy Greer as girls in an exclusive clique in their high school who inadvertently kill their friend. Though the film was a box-office failure, it went on to earn a cult following in subsequent decades.