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In 1999, Cook starred her breakout role in the sleeper hit film She's All That, a romantic comedy that adapted George Bernard Shaw's Pygmalion and so far the most financially successful film in her career.

In 2000 she starred opposite Elijah Wood in the well-received The Bumblebee Flies Anyway.

She took the lead role in 2001's Josie and the Pussycats, which turned out to be a box office failure.

After that Cook mainly focused her work in independent films, resulting in some nicknaming her the next " Indie Queen " after Parker Posey.

She also appeared as a main cast in the 2005 television miniseries Into the West produced by Steven Spielberg and Dreamworks.