Over the past 25 years, Reese Witherspoon has become one of the great movie stars of her generation. Since first emerging on the scene in a series 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 over the course of her decades of stardom.
Few actresses are more versatile or charming than she continues to be to this day, and these are the five movies you should start with if you’re looking to catch her best work.
Walk the Line (2005)
The movie that Witherspoon won her Oscar for, Walk the Line is really more about Joaquin Phoenix’s Johnny Cash than it is about Witherspoon’s June Carter.
While Phoenix may get more screen time, though, it’s hard to deny that Witherspoon packs the bigger punch, perfectly playing every scene as the chemistry between the two of them grows. Walk the Line has been lampooned as a conventional biopic, but there’s real emotion in Witherspoon’s performance, and she also proves that she’s a pretty decent singer.
Election (1999)
Perhaps the movie that first proved that Witherspoon was a legit star, Election follows a strange, perverse feud between a successful high school student who is running for class president and the History teacher who wants to make sure that she doesn’t succeed.
Election feels like a remarkably prescient movie about male rage, but it’s also an acidic comedy that’s hugely entertaining from front to back. Alexander Payne has gone on to prove that he’s one of the great directors working today, and Election was the movie that put both him and Witherspoon firmly on the map.
Legally Blonde (2001)
Witherspoon’s full-blown movie star role, Legally Blonde was also definitive proof that Witherspoon can play broad comedy. Telling the story of Elle Woods, a recent college graduate who was a sorority queen, and decides to apply to Harvard Law School, the movie is certainly a little ridiculous, but it’s also incredibly satisfying.
What’s more, this is a movie that is entirely carried 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)
An adaptation of a 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 downward trajectory by hiking the Pacific Crest Trail, even though she has basically no outdoor experience. Wild is a movie all about isolation, and Witherspoon carries it off beautifully.
The movie also features an excellent supporting turn from Laura Dern (Jurassic World Dominion) as Strayed’s mother. Wild‘s depiction of Strayed’s turmoil, and the beauty of its outdoor scenery, make this one of the most compelling movies that Witherspoon has ever made.
Pleasantville (1998)
One of Witherspoon’s best early roles, Pleasantville tells the story of two modern teenagers who find themselves transported into a sitcom from the 1950s. Witherspoon and Spider-Man actor Tobey Maguire are excellent as two teenagers who find themselves at turns charmed and disturbed by the way this world is set up.
Pleasantville is a world almost entirely devoid of conflict, and the movie’s ostensible point is that its rose-tinted nostalgia may seem great, but only because it covers up a lot of what makes life wonderful. Its central metaphor may feel a little heavy-handed, but Pleasantville still holds up 25 years later.
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