The film became a box office success and a cult classic. 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.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.
She can do anything." 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 still hate her.' So we had to make sure she was the kind of person you just can't hate." Meanwhile, the Seattle Post-Intelligencer concluded, "Witherspoon is a talented comedian who can perk up a scene just by marching in full of pep and drive and she powers this modest little comedy almost single-handedly." For her work, Witherspoon garnered her second Golden Globe Best Actress nomination and an MTV Movie Award for Best Comedic Performance.
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." The 2001 film Legally Blonde marked a turning point in Witherspoon's career; she starred as Elle Woods, a fashion-merchandising major who decides to become a law student in order to follow her ex-boyfriend to Harvard Law School. In 2002, after the success of Legally Blonde, Witherspoon starred in several roles, such as Greta Wolfcastle in The Simpsons episode "The Bart Wants What It Wants", and as Cecily in the comedy The Importance of Being Earnest, a film adaptation of Oscar Wilde's play in which she received a Teen Choice Award nomination.
She said that it gave her "a sense of family and tradition" and taught her about "being conscientious about people's feelings, being polite, being responsible and never taking for granted what you have in your life." 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.
According to The Guardian, her performance made an early impression.
In 2003, Witherspoon followed up the success of Legally Blonde by starring in the sequel Legally Blonde 2: Red, White & Blonde.