Best: 'Election' (1999): This film saw Reese Witherspoon nominated for several major awards including American Comedy Awards for Funniest Actress in a Feature Film.
Election' (1999): The film garnered a positive reaction from critics, with the Washington Post noting.
Election' (1999): The film was nominated for an Oscar for Best Adapted Screenplay and drew praise from The New York Times.
Worst: 'Best Laid Plans' (1999): not the best film associated with the actress, the plot revolves around Kathy (Witherspoon), a young girl who approaches Bryce.
Best Laid Plans' (1999): Indeed, The Guardian bemoaned the fact that a promising cast and some good performances were completely wasted on the film.
'Little Nicky' (2000): The actress appeared in this comedy starring Adam Sandler, who plays the devil's son.
Little Nicky' (2000): The Washington Post panned the film as more silly than inventive, with just a sprinkling of slightly amusing jokes.
Little Nicky' (2000): Furthermore, Rolling Stone insisted that despite the attempt to make a successful film based on the profitability of Adam Sandler.
Legally Blonde' (2001): A defining role for Witherspoon, and the one for which she is best remembered. Her performance garnered a Golden Globe nomination for Best Actress in a Musical Film or Comedy.
Legally Blonde' (2001): The film in general divided critics, but Witherspoon's performance was highly praised. TV Guide Magazine.
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