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The following year, she starred in the romantic comedy Sweet Home Alabama, which emerged as her biggest live-action commercial success.

Witherspoon's breakthrough role was playing Elle Woods in the 2001 film Legally Blonde, for which she received her second Golden Globe nomination.

Also that year co-starred with Sarah Michelle Gellar and Ryan Phillippe in the drama film Cruel Intentions, a modern take on the 18th-century French novel Les Liaisons Dangereuses.

The San Francisco Chronicle praised her performance as Annette Hargrove: "Witherspoon is especially good in the least flashy role, and even when called upon to make a series of cute devilish faces, she pulls it off." She also appeared in a music video by Marcy Playground for the film's soundtrack.

The film became a box office success and a cult classic.

Next came perhaps Witherspoon's career-defining role: starring with Matthew Broderick in Election, based on Tom Perrotta's novel; for her portrayal of Tracy Flick, she received vast critical acclaim and won the Best Actress Award from the National Society of Film Critics and the Online Film Critics Society, a first Golden Globe nomination and an Independent Spirit Award nomination.

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