Election (1999): Witherspoon will always be Tracy Flick — the balance she finds here is so delicate and difficult. She's playing an essentially unlikable character: a prim, scheming know-it-all who will do whatever it takes to be voted president of her high school's student government. Adorable and annoying at once, Witherspoon makes us ultimately sympathise with her.
Walk The Line (2005): Witherspoon as Johnny Cash's lifelong love, June Carter, pretty much steals the movie right out from underneath Joaquin Phoenix. This was the first truly grown-up, womanly role she'd played at this point, and she got to be not just an engaging on-stage performer but also a wife, mother, caretaker and no-nonsense family backbone. This earned her the Academy Award for best actress.
Legally Blonde (2001): Witherspoon is the ebullient Elle Woods, a pampered campus princess who finds her true voice in the unlikeliest of places: Harvard Law School. She is just irresistible here in the classic ditzy-blonde mode. As the saying goes, you have to be pretty smart to play dumb.
Freeway (1996): She stars as Vanessa, a trashy teenager who ends up hitching a ride with a youth counsellor named Bob in the hope of finding her grandmother. She opens up to him but eventually realises he's a serial killer. High-spirited and foul-mouthed, the sight of Witherspoon pistol-whipping and berating Kiefer Sutherland in her girlish Southern twang is a hoot.
Pleasantville (1998): She uses her comic timing to great effect here as a sassy and subversive teenager who gets unwittingly sucked into the television set with her twin brother and finds herself in the idyllic, fictional 1950s town of Pleasantville.