She began her acting career in the late 1990s, guest starring in episodes of the CBS dramas Touched by an Angel and Promised Land, before being cast as Jessica Bennett in the NBC soap opera Passions, a role she played from 1999 to 2000. She subsequently appeared in the short-lived CBS drama series Wolf Lake (2001-2002), and in the made-for-television film Monster Island (2002).

Trying her hand at comedy, she went the independent film route as the Jewish daughter of a large, zany family in the indie feature Checking Out, but her screen time fared better in the more mainstream Walt Disney Pictures confection Sky High, which was both financially and critically successful. She starred as Gwen Grayson, the in-disguise alter ego of the supervillain Royal Pain.

After the Read more...

In 2007, she appeared in a pair of high-profile event films. Quentin Tarantino cast her as a well-intentioned but vapid and naïve actress in his high-speed segment of Grindhouse titled Death Proof, his half of a double-billed feature. The film failed to produce ticket sales, but drew critical acclaim. The same summer, hot off the heels of its release, Winstead received another shot at action Read more...