Heskin' first role came in early 1998, when Director John Woo selected her as the lead in his pilot Blackjack starring Dolph Lundgren and Kate Vernon. Later that year, she replaced Vanessa Dorman as Caitlin Richards Deschanel on the NBC daytime soap opera Sunset Beach. Heskin portrayed the role until the end of the show, December 31, 1999. She later guest-starred on The WB shows include 7th Heaven, Angel, and Charmed. Heskin later returned to daytime television, briefly replacing McKenzie Westmore as Sheridan Crane on Passions in 2006 and 2008, while Actress was on a leave of absence on two separate occasions.

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).