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This pregnancy was not a hindrance to her work as Witherspoon believed the gestation had in fact helped her portrayal of Sharp's character: "I love the luminosity that pregnancy brings, I love the fleshiness, I love the ample bosom—it gave me much more to play with", she said.
The film and Witherspoon's portrayal of Sharp received mixed reviews, as The Hollywood Reporter wrote, "Nair's cast is splendid.
Her performance received good reviews and garnered her the Young Hollywood Award for Best Female Breakthrough Performance.
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.
She serves on the board of the Children's Defense Fund (CDF) and was named Global Ambassador of Avon Products in 2007, serving as honorary chair of the charitable Avon Foundation.
she was instead cast for the lead role of Dani Trant, a 14-year-old country girl who falls in love for the first time with her 17-year-old neighbor.
as Nicole Walker, a teenage girl who starts dating a man with obsessive tendencies, and the black-comedy thriller Freeway, alongside Kiefer Sutherland and Brooke Shields, where she held the lead role. Among them was the San Francisco Chronicle, with Mick La Salle commenting, "Witherspoon, who does a Texas accent, is dazzling, utterly believable in one extreme situation after the other." In Pleasantville, she starred with Tobey Maguire in a tale about 1990s teenage siblings who are magically transported into the setting of a 1950s television series.
She portrayed Jennifer, the sister of Maguire's character who is mainly concerned about appearances, relationships and popularity.
The sequel was not as financially successful as the first film and it generated mostly negative reviews.
USA Today considered the movie "plodding, unfunny and almost cringe-worthy", but also noted that "Reese Witherspoon still does a fine job portraying the fair-haired lovable brainiac, but her top-notch comic timing is wasted on the humorless dialogue." In 2004, Witherspoon starred in Vanity Fair, adapted from the 19th-century classic novel Vanity Fair and directed by Mira Nair.