Over the past 25 years, Reese Witherspoon has become one of the greatest movie stars of her generation. Since first appearing in a string of comedies, Witherspoon has definitively proven that she can be funny and dramatic in equal measure, and she’s created a number of indelible roles throughout her decades of fame.
Few actresses are more versatile or captivating than her to this day, and here are five films you should start with if you want to get her best work.
Walking the Line (2005)
The film for which Witherspoon won her Oscar, Walk the Line it’s actually more about Joaquin Phoenix’s Johnny Cash than Witherspoon’s June Carter.
While Phoenix may get more screen time, it’s hard to deny that Witherspoon packs a bigger punch, perfectly nailing each scene as the chemistry grows between the two of them. Walk the Line has been lampooned as a conventional biopic, but there’s real emotion in Witherspoon’s performance, and she also proves she’s a pretty good singer.
Election (1999)
Perhaps the film that first proved Witherspoon was a legitimate star, Election follows the strange and twisted feud between a successful high school student running for class president and a History teacher who wants to make sure he doesn’t succeed.
Election feels like a coming-of-age film about male rage, but it’s also a highly entertaining acid comedy from front to back. Alexander Payne has proven that he is one of the great directors working today, and Election was the film that put him and Witherspoon firmly on the map.
Legally Blonde (2001)
Witherspoon’s complete film star roles, Legally blonde is also definitive proof that Witherspoon can play broad comedy. Telling the story of Elle Woods, a college graduate who becomes a sorority queen, and decides to enroll at Harvard Law School, this film is certainly a little silly, but also very satisfying.
What’s more, this is a film carried entirely by Witherspoon. It wouldn’t have worked with any other actress, and it remains one of the biggest hits of Witherspoon’s entire career.
Wild (2014)
Adapted from the memoir of the same name, Wild tells the story of Cheryl Strayed, a woman who finds her life spiraling out of control and decides to halt her decline by hiking the Pacific Crest Trail, despite having essentially no outdoor experience. Wild is a film about isolation, and Witherspoon displays it beautifully.
The film also features a wonderful supporting role from Laura Dern (Jurassic World Domination) as Strayed’s mother. WildStrayed’s depiction of chaos, and the beauty of the outdoor scenes, make this one of the most compelling films Witherspoon has ever made.
Pleasantville (1998)
One of Witherspoon’s best early roles, funville tells the story of two modern teenagers who find themselves transported into a sitcom from the 1950s. Witherspoon and Spider Man Actor Tobey Maguire is superb as two teenagers who find themselves fascinated and disturbed by the way the world is set up.
funville is a world almost entirely devoid of conflict, and the point of the film is that rose-tinted nostalgia may seem great, but only because it glosses over much of what makes life beautiful. The main metaphor may feel a bit heavy-handed, however funville still holds up 25 years later.
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