Reese Witherspoon has been appearing in feature movies since 1991 and some of her best movies cover popular comedies to critically acclaimed Academy Award winners. Whether it's depicting real-life figures, completely original and relatable protagonists, or bubbly women who are never caricatures, Witherspoon has proven herself to be a talented actor with incredible range. Many may remember Witherspoon first from her appearance in The Man in the Moon as Dani Trant and since then, she has been frequently working and producing multiple projects a year. It’s a testament to her ability that she can jump in and out of demanding parts with little time in between.
Witherspoon has worked in rom-coms to hard dramas with notable directors and actors and has earned a trove of awards. She has been nominated twice for Academy Awards (winning once in 2006), four times for Golden Globes for acting in film (winning in 2006), and twice at the SAG awards for movie roles (again, winning in 2006). Witherspoon’s movies often put her in the role of a typical type A who proves to be more than capable despite what those around her think. She seems like someone everyone would want to be friends with and is effortlessly charming. Witherspoon’s best movies are the ones that lean into those strengths.
12 Monsters Vs. Aliens (2009)
Witherspoon starred in Monster vs. Aliens, an animated comedy from DreamWorks, that has led to a successful franchise (including Monsters vs. Aliens: Mutant Pumpkins from Outer Space, in which Witherspoon returned). This animated movie follows Susan Murphy, voiced by Witherspoon, an everyday woman whose life is turned upside down when she transformed into Ginormica, a super-sized human. She and a secret team of monsters join together to stop an alien invasion. It isn’t the strongest DreamWorks offering in memory, with a 74% on Rotten Tomatoes, but it's a fun comment on Witherspoon’s own persona and a pseudo-Suicide Squad movie before the DCEU took interest.
11 Inherent Vice (2014)
Paul Thomas Anderson’s Inherent Vice is one of the more divisive movies in his filmography with some finding the complicated plot difficult to follow and connect with. The movie depicts Larry "Doc" Sportello (Joaquin Phoenix), a private eye who is embroiled in a criminal underworld as he tries to solve multiple interconnected crimes. Witherspoon plays DA Penny Kimball, Doc’s on-again, off-again girlfriend. The movie is in the vein of Anderson’s Licorice Pizza and Magnolia with its chaotic story and large cast. Witherspoon’s Kimball is well-picked as the smart, ambitious attorney opposite Phoenix's paranoid, messy private eye. Her squinting apprehension at Doc also adds to the mystery of Anderson’s caper.
10 Freeway (1996)
Freeway is a dark comedy fantasy movie that’s a take on the “Little Red Riding Hood” fairy tale. With character names like Robert “Bob” Wolverton (Kiefer Sutherland), Chopper Wood (Bokeem Woodbine), and Vanessa Julia Lutz (Witherspoon), the film could have easily been a schlocky, B-movie. Instead, thanks to Witherspoon’s performance, Freeway is a captivating and ridiculous movie that revels in its tropes. Everyone involved knows what sort of movie they’re in and Witherspoon’s unpredictable acting helps deliver a captivating performance. It was not a box office hit, but Freeway is acclaimed with a 77% on Rotten Tomatoes, and the chemistry between Sutherland and Witherspoon makes it a surprising success.
9 The Good Lie (2014)
Witherspoon has the impressive ability to make premises that might be overly sentimental feel real. The Good Lie, a movie about a family of refugees from Sudan trying to survive in America, could have run into several controversial issues if the filmmakers weren’t careful. Instead, it’s an honest look at a terrible trauma and brutality of the situation, but also doesn’t forget that there is humor and warmth in even the worst situations. Witherspoon plays Carrie Davis, an overworked employment counselor who helps the refugees find work, and she deftly steps into the background whenever possible in order to let the story of the Sudanese survivors take center stage.
8 The Man In The Moon (1991)
The Man in the Moon Witherspoon's first movie and with 91% on Rotten Tomatoes, it can now be looked back at as a portent of how successful the young actor would go on to be. Witherspoon plays Danielle "Dani" Trant, a 14-year-old teenager from Louisiana who starts to develop feelings for a boy who moves next door. It is a poetic coming-of-age drama that is bittersweet and honest. Witherspoon’s ability to hold up the film alone in a difficult role (and at a young age) was an early sign of the fearless way she would take on future parts.
7 Cruel Intentions (1999)
A modern retelling of Pierre Choderlos de Laclos' 1782 novel Les Liaisons dangereuses, Cruel Intentions stars Witherspoon, Ryan Philippe, and Sarah Michelle Gellar, which involve a love triangle of rich, bored high schoolers who intermix sex, romance, and jealousy. Like the novel, Gellar and Phillipe’s characters make a bet on how soon Phillippe’s character can seduce Witherspoon’s. Cruel Intentions is, at times, shocking and ridiculous but the movie has since grown in appreciation for that very same reason and is currently something of a cult classic. It’s a time capsule of the '90s and a lot of fun to revisit, not least because of Witherspoon’s earnest portrayal of Annette Hargrove.
6 Pleasantville (1998)
Pleasantville is a high-concept fantasy that thrusts siblings David (Tobey Maguire) and Jennifer (Witherspoon) into the 1950s - literally. David and Jennifer are magically transported into their favorite television show, Pleasantville, a black-and-white 1950s sitcom about a small, idyllic town. David and Jennifer introduce real-world emotions and concepts to the one-dimensional figures and the world slowly switches from black-and-white to color (and is better for it). It’s a very original idea, and it was nominated for three Academy Awards at the 71st Oscars. Witherspoon is wide-eyed and smiling, necessary to depict the optimistic Jennifer, who leads the charge to bring life to a muted town.
5 Mud (2012)
As one of the first movies in the “McConaissance”, Mud is most famous for adjusting the world to the idea that Matthew McConaughey was about to become a serious and critically acclaimed actor. What might be forgotten in the 98% Rotten Tomatoes scoring film is that Witherspoon plays the critical role of Juniper, Mud’s (McConaughey) girlfriend, and the reason he is a fugitive in the movie. Juniper is a much less self-possessed character than Witherspoon usually plays. The actor shows her incredible range as the nervous, emotional, but ultimately strong Juniper (gelling well alongside McConaughey in one of his favorite roles).
4 Wild (2014)
Wild is a biopic based on Cheryl Strayed’s memoir about her solo trip along the Pacific Crest Trail (PCT). Witherspoon produced the movie and plays Cheryl, who takes on the hike in order to reconnect with her dead mother. Much of the movie depicts Cheryl alone, and it's at these times Witherspoon shows some of her best acting. Appearing beleaguered and unsure, Witherspoon use her facial expressions and mannerisms depict a woman struggling to reckon with her past and her future. For her work, she was nominated in the Best Actress category at the SAGs, Golden Globes, and Academy Awards.
3 Legally Blonde (2001)
Witherspoon’s Elle Woods may be the most quotable character of her career. Legally Blonde follows Woods as she attends Harvard in order to earn a law degree and impress her ex-boyfriend. There, Elle’s valley-girl mentality clashes with the East Coast elite ethic, and she learns what she’s capable of when she applies herself. Most people underestimate Woods for her blonde hair and sorority girl personality, but she proves to be a kind, popular, and most of all intelligent lawyer by the end of the movie.
2 Walk The Line (2005)
Walk the Line follows the story of Johnny (Joaquin Phoenix) and June Carter (Witherspoon) Cash. For her part as the real-life singer, Witherspoon won the SAG, Golden Globe, and Academy Award for Best Actress. Witherspoon learned to sing for her role as the hugely recognizable June Carter and brings key excitement and energy to a movie that is often filled with depression and sadness. While the movie does depict Johnny Cash’s struggles with sobriety, the movie also shows the raw and emotional love story between Carter and Cash, and Witherspoon’s radiant smile no doubt mirrors what Johnny saw when he realized he was in love with June Carter.
1 Election (1999)
Alexander Payne’s second movie, Election, is a dark comedy told via voiceover of teacher Jim McAllister (Matthew Broderick) and students Tracy Flick (Witherspoon), Paul Metzler (Chris Klein), and Tammy Metzler (Jessica Campbell). Tracy is an iconic antagonist, an overachieving, good-at-everything, aggressive, and ruthless high school student set on not only winning, but beating everyone around her (even up until the end of Election). This was Witherspoon’s first foray into comedy and opened up a whole second career for the actor who earned a Golden Globe nomination for her work. Reese Witherspoon perfectly plays the all-too-relatable uptight student with a clipped speech pattern and physical tightness of her face and posture.