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The young actress began starring in a string of MOWs. She had the lead role in “Airspeed” (HBO, 1998), an adventure-thriller about a spoiled 13 year-old forced to fly her father’s private jet after a bolt of lightning knocks everyone else onboard unconscious. Next was “Time at the Top” (Showtime, 1999), where Cuthbert—then 16—played a 13 year-old who discovers a time machine and travels back to 1881 in order to help a young girl and her family. In “Mail to the Chief” (ABC, 1999), Cuthbert continued playing the good girl in the Wonderful World of Disney production about the President of the United States striking up a friendship with an eighth-grader in order to get back in touch with real people.
As she got older, Cuthbert’s growing sex appeal became too pronounced to ignore, so she took on more adult roles. In “My Daughter’s Secret Life” (Lifetime, 2001), Cuthbert played a 17 year-old girl living a privileged existence who suddenly develops a serious gambling addiction. Cuthbert won a Gemini Award for Best Actress in a Dramatic Program or Mini-Series, an honor bestowed by the Academy of Canadian Cinema & Television.
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Cuthbert got her chance to star in a feature in “The Girl Next Door” (2004), playing a young teen's sexy house-sitting neighbor who turns out to be a porn star who wants out of the business. At first the idea of playing a porn actress didn’t appeal to the actress, but her agent encouraged her to read the script anyway. Half-way through the read, Cuthbert knew she wanted to make it--she only half-joked that she and her agent went through a rigorous back-and-forth negotiation with the filmmakers over exactly how much of the actress' body would be revealed on-screen--in the end the film revealed more of Cuthbert's easy warmth and charisma than her skin. Always serious about her craft, Cuthbert did extensive research by thumbing through Playboy and Hustler, while hanging out with stars of San Fernando Valley’s chief export.
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Meanwhile, Cuthbert’s work on “24” continued through its third season (the actress earned a nomination for the 2002 Teen Choice Award for Breakout TV Actress), but her character was not a part of the fourth season in 2005, which freed her to seek out more big screen roles. First up was the sub par horror remake "House of Wax" (2005), playing an all-too-typical slasher flick heroine, this time with a brooding twin brother, whose road trip with pals is disrupted when they visit a creepy wax museum in an isolated town. Her next film, “The Quiet” (2006), proved to be an emotionally trying experience—she played a sexually abused teenager whose familial secrets are divulged when her parents (Edie Falco and Martin Donovan) adopt a recently orphaned girl (Camilla Belle). She was next cast to star in “My Sassy Girl” (lensed 2006), a remake of the South Korean romantic comedy of the same name about an awkward shy guy who falls in love with a free-spirited girl he meets on the subway.