At the age of 20, Mary guest starred in a season one episode of the hit televison series
"Tru Calling", about a woman who could relive days to save future potential homicide victims. She plays the na”ve role of Bridget Elkins in the episode
"Closure". Later that year, Mary appeared in a low-budget, made-for-TV, MTV production movie,
"Monster Island" alongside Carmen Electra and Nick Carter. She plays the role of Maddison, one of the unlucky students of a summer vacation who finds herself trapped in an island inhabited by giant monsters. The film was not received well by critics and fans alike, but it had at least improved Mary's resume.
Mary further concentrated on roles in movies. When 2005 arrived, Mary started the rise to spotlight. She appeared in the horror sequel to the American remake of
"The Ring". She plays an almost non-existent role of 16-Year-Old Evelyn (having only appeard in the unrated edition and had an approximate screentime of seventeen seconds), in Hideo Nakata's 2005 horror,
"The Ring Two". "I had to cry and be very emotional, but it had to be creepy at the same time," Mary says about the role. The movie, again, received negative reviews, and Mary's career goes on.
Instead, Winstead tried her hand in comedy and nabbed a role in the independent film,
"Checking Out". In the movie, she plays Lisa Apple, a member of a dysfunctional Jewish family. Although the film did not succeed financially, the film won several nominations and at least, Mary had found her silver screen debut.
Among heavyweights in Sky High.
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Nevertheless, the star received her big break in the superhero comedy
"Sky High", which was released later the same year. She was given the role of Gwen Grayson, both a loved and hated high school persona. Gwen was a technopath and was able to control technology. Undoubtedly, Gwen Grayson was Mary's most convoluted and complex role to date. She says, "She is the quintessential girl next door and evolves throughout the movie into something else. There are a lot of complexities in her character which made it so much fun". Mary starred alongside distinguished stars, Kurt Russell and Kelly Preston. "I had a scene with both of them the first day that I was on the set and I was struck by how funny and down to earth they both were," Mary recalls. "It was funny seeing Kurt in his super hero costume, then chatting normally, asking everybody if they want a tuna sandwich." The film was a success, both critically and financially, and from the on, Mary's career went uphill.
