1999 would prove to be Coughlan's breakthrough year, starring alongside Katie Holmes in Williamson's directorial feature "Teaching Mrs. Tingle", a much-awaited black comedy. She cemented her "one to watch" status with a featured role in the ensemble of the college campus set psychothriller "Gossip" (2000). After appearing in a pair of poorly performing comedies in 2001 ("Freddie Got Fingered" and "Super Troopers"), Coughlan again returned to more independent-minded features when she appeared in 2002's "Pumpkin" with Christina Ricci, Hank Harris and Dominique Swain.