Leerhsen made her film debut in the short film "Junior Creative" (2000), as Sarah, and shortly afterwards, she appeared in the horror sequel "" (2000), though she originally auditioned for the part that eventually went to Kim Director. Upon its premiere, the sequel received extremely negative reviews by critics, but grossed US$26.4 million in North America, and went on to gross US$47.7 million globally. She was nominated for the Fangoria Chainsaw Award for her supporting role in that movie. Leerhsen's profile raised significantly and her work in the film was followed by a number of appearances on television. In 2001, she guest-starred in an episode of the third season of "The Sopranos", where she played a lesbian tennis instructor who falls for Drea de Matteo's character, and became a member of the cast of the television series "The Guardian", where she played Amanda Bowles, an ambitious but caring associate, who leaves midway through season one. She played a supporting role in Woody Allen's "Hollywood Ending". Screened out of competition at the 2002 Cannes Film Festival. the film garnered a mixed critical response while it grossed a lukewarm US$14.5 million at the end of its theatrical run.