9 Milestones in the Evolution of Reese Witherspoon

Pleasantville (1998)

After Fear, Reese Witherspoon scored the role of Jennifer in Gary Ross's retro fantasy drama. As a shallow high schooler, she (and her twin brother played by Tobey Maguire) becomes trapped inside the fictional 1950's sitcom Pleasantville where her modern values influence (and literally discolor) the town's old-fashioned ideals.

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Election (1999)

Witherspoon's role as pathological small town overachiever Tracy Flick earned the actress her first Golden Globe nod in Alexander Payne's Oscar-nominated script. Starring opposite Matthew Broderick (as an embittered high school teacher who views Flick as his mortal enemy), the actress demonstrates her ability to play potently perky, naive, lonely and emotionally damaged in one powerhouse performance.

Election (1999) by m0vietrailerpark

Legally Blonde (2001)

After proving that she could play the complicated outcast, Reese Witherspoon went mainstream for the highest grossing movie of her career at the time. In Legally Blonde, Witherspoon plays Elle Woods, a ditsy sorority girl who tries to win back her boyfriend by getting a Harvard Law degree -- only to realize that she, her true friends and a standoff-ish attorney deserve priority in her decidedly "Marilyn" life. Here, Witherspoon proved that she could carry a film and that brainy blondes who know how to accessorize are inspiring. Legally Blonde would spawn a sequel, a musical and a made-for-TV-movie produced by Witherspoon, Legally Blondes.

Sweet Home Alabama (2002)

Witherspoon starred in her first official romantic comedy a year later. As Melanie Smooter, a successful fashion designer who has to divorce her childhood sweetheart (Josh Lucas) so that she can marry the mayor's son (Patrick Dempsey) -- Melanie returns home only to revert to her stubborn Southern personality and, you guessed it, fall back in love with her first husband. This film, which is still Witherspoon's biggest commercial film success, would be the first in a string of romantic comedies for her including Just Like Heaven, Four Christmases and How Do You Know.

Walk the Line (2005)

Witherspoon made the leap from rom-com to biographical drama for her Oscar-winning turn as June Carter Cash in James Mangold's Walk the Line. She sang, she danced, she nursed Joaquin Phoenix's Johnny Cash back to health and she proved to be the strongest piece in this onscreen collaboration.

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