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In 1999, Witherspoon starred alongside Alessandro Nivola in the drama thriller Best Laid Plans ; she played Lissa, a woman who schemes with her lover Nick to escape a small, dead-end town.

In this same year, she 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.

Her performance as Annette Hargrove was praised by the San Francisco Chronicle: " 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.

" Coincidentally, she appeared in a music video by Marcy Playground for the film's soundtrack.

In the same year, Witherspoon and Matthew Broderick starred in the film adaptation of the 1998 novel Election by Tom Perrotta.

She portrayed Tracy Flick, a competitive and ambitious over-achiever who runs for student body president.

She received vast critical acclaim for her performance 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 also received a rank on the list of 100 Greatest Film Performances of All Time by Premiere.

Academy Award – winning director Alexander Payne praised her: " She's got that quality that men find attractive, while women would like to be her friend.

But that's just the foundation.

Nobody else is as funny or brings such charm to things.

She can do anything.

" In spite of her successful performance, Witherspoon noted in an interview that she struggled to find work after completing the film, due to typecasting.

When analyzing the reasons behind her difficulty to find work, Witherspoon commented " I think because the character I played was so extreme and sort of shrewish – people thought that was who I was, rather than me going in and creating a part.

I would audition for things and I'd always be the second choice – studios never wanted to hire me and I wasn't losing the parts to big box office actresses but to ones who I guess people felt differently about.