Skye made her first television appearance on the show Total Security in 1997. Then she played a couple of smaller parts on Touched by an Angel and Chicago Hope, and made appearances in a number of television movies before she was cast for the role as "Jane" in Zoe, Duncan, Jack and Jane in 1999. Zoe..., as the show was renamed for the second season, was a short-lived (two seasons) sitcom about four teenagers - Skye's character being one of them. In 2000, the same year that Zoe... ended, Skye's first major movie production premiered. In 28 Days, she starred alongside Sandra Bullock and Viggo Mortensen.