In 1996, the striking, dark-haired performer made her film debut with a one-line role as a former girlfriend of "Jerry Maguire" (Tom Cruise) in Cameron Crowe's hit romance. She followed up with a guest role on "Seinfeld" (NBC) and a turn in the supernatural ABC TV-movie "Devil to Pay" the following year. Still a relative unknown, Milicevic returned to the big screen with a small role in the spy thriller "Enemy of the State" in 1998, the same year that she had her first series regular role. Unfortunately, Milicevic debuted in "The Army Show", an uninspired sitcom that had a short run on The WB. Later in 1998, she began a recurring role on the network's college-set drama "Felicity". The next year, two of her feature acting roles skipped the theater and bowed on cable ("Postmortem" on Cinemax and "Kiss the Sky" on The Movie Channel), but by 2001 she was back with a memorable turn as a Russian model in the unimpressive romantic mystery "Head Over Heels". Milicevic reteamed with Crowe and Cruise for "Vanilla Sky" later in 2001 but her regular role on the highly-touted HBO series "The Mind of the Married Man" (2001- ) would prove the boost Milicevic's career needed, the actress becoming instantly notable thanks to the eyebrow-raising role her character plays in her boss' fantasies.