In 2000, Heskin played the female lead role in the thriller film Held for Ransom. The movie was released direct-to-video, never gaining a theatrical release in the United States. She later had small parts in Tomcats, Planet of the Apes and Catch Me If You Can, before leading role in the independent comedy film Pride & Prejudice: A Latter-Day Comedy (2003). In 2005, she had role in the box office bomb comedy Dirty Love starring Jenny McCarthy. The following year, she was cast as Paige Morgan (replacing Julia Stiles) in the romantic comedy film The Prince & Me 2: The Royal Wedding, a sequel to the 2004 film The Prince and Me. She later has starred in The Prince and Me 3: A Royal Honeymoon (2008), and The Prince and Me 4: The Elephant Adventure (2010).