Skye got an early start in the business, beginning her acting career in community theater at the age of three. By age 11 she had had taken her show on the road, touring Europe with the Santa Monica Playhouse theater group. The actress made her TV debut in the 1997-1998 season with guest roles on "Touched by an Angel" and "Chicago Hope" (both CBS) and a featured part in the Showtime TV-movie "Horton Foote's Alone". In 1998, Skye co-starred in the ABC children's thriller "R.L. Stine's Ghosts of Fear Street", playing Cricket, an insect enthusiast whose father metamorphoses into a bug whenever hit with undue stress. Later that year, she played a young runaway alongside screen legend Maureen O'Hara in the touching family film "Cab to Canada" (CBS).
Skye made her big screen debut with a small role in Ron Howard's media satire "EDtv" (1999). Next, she was featured in "Town & Country" (2001), a romantic comedy with Warren Beatty and Diane Keaton and "28 Days", a rehab-set feature starring and produced by Sandra Bullock.
The young thespian continued to find herself cast in a wide range of projects. She appeared in Barry Levinson's heist drama "Bandits" (2001) and starred in the well received TV movie "Confessions of an Ugly Stepsister" (2002). In addition to a guest appearance on the popular new series "Smallville" in 2002, she also had a small part in the indie sleeper "The Salton Sea."