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Witherspoon owns a production company Hello Sunshine, a clothing company Draper James, and she is actively involved in children's and women's advocacy organizations.

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Witherspoon was raised as an Episcopalian, and has said she is proud of the "definitive Southern upbringing" which she received.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.Witherspoon regarded this as a "personal role" in that it reminded her of experiences she had when she moved from her hometown Nashville to Los Angeles.In 2003, Witherspoon followed up the success of Legally Blonde by starring in the sequel Legally Blonde 2: Red, White & Blonde.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.

Her leading role of Tracy Flick in Election (1999) was nominated for a Golden Globe Award.

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

In 2014, Witherspoon produced the thriller Gone Girl and received critical acclaim for portraying Cheryl Strayed in Wild, for which she earned her second Academy Award nomination for Best Actress and a fourth Golden Globe nomination.

In 2017, she co-produced and starred in the HBO drama series Big Little Lies, for which she received two Primetime Emmy Award nominations for Outstanding Lead Actress in a Miniseries or a Movie and Outstanding Limited Series, winning the latter as a producer.

Director Alexander Payne said of her, "She's got that quality that men find attractive, while women would like to be her friend. Nobody else is as funny or brings such charm to things.