Reese Witherspoon is undoubtedly one of the most well-known and successful actresses of our time. Named the world’s highest-earning actress in 2021, Witherspoon has spent her thirty-some-year career showcasing her talents as an actress and producer. Recipient of an Academy Award, an Emmy, and two Golden Globes, Reese Witherspoon is a cut above the rest.
Because Witherspoon has had such a long career, many of her best movies have fallen out of public consciousness for a focus on new releases. However, her filmography is extensive, impressive, and nostalgic for long-term fans. Here are twelve of the best Reese Witherspoon movies that deserve a rewatch — and we don’t just mean Legally Blonde, although that will always have a special place in our hearts.
12. How Do You Know (2010)
In this lighthearted romantic comedy, Reese Witherspoon stars alongside Paul Rudd, Owen Wilson, and Jack Nicholson as a young softball player caught in a love triangle. Wilson and Rudd act as foils of one another, a baseball player and businessman, respectively, in pursuit of Witherspoon’s affections. Though this is one of Witherspoon’s lesser-known films, it stands out for its star-studded cast, high-budget production, and fun plot. If you’re in search of a comforting film with charm, this is one of the best Reese Witherspoon movies and deserves rewatch.
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11. Sweet Home Alabama (2002)
A nostalgic, classic romcom, Sweet Home Alabama stars Reese Witherspoon alongside Patrick Dempsey and Josh Lucas. Witherspoon owns the stage as a powerful fashion designer engaged to the NYC mayor’s prominent and attractive son, only to return to her Alabama home and confront her ex-husband for a legal divorce. This film is lighthearted, humorous, and romantic, sweeping the best parts of the genre into one film.
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10. Monsters vs. Aliens (2009)
The only animated film to make this list, Monsters vs. Aliens stars Reese Witherspoon as Susan Murphy, a local weatherman’s fiancee, before she is struck by a meteorite that turns her into a 50-foot tall giantess, Ginormica. As she is whisked away to a top-secret government facility for monsters, she encounters several other creatures and builds a familial relationship with each of them, eventually culminating in a battle between the monsters and an extraterrestrial overlord, Gallaxhar, who plans to invade Earth.
Witherspoon brings Ginormica to life in this performance, bolstered by the talents of co-stars Seth Rogen, Paul Rudd, Rainn Wilson, Keefer Sutherland, Hugh Laurie, Will Arnett, and Stephen Colbert.
9. Inherent Vice (2014)
In this Paul Thomas Anderson film, Reese Witherspoon joins an impressive ensemble cast alongside Joaquin Phoenix, Josh Brolin, Owen Wilson, Benicio del Toro, Martin Short, and more. Portraying Penny, one of the Doc’s lovers in the film, Witherspoon acts as a driving force. Her character, as an assistant district attorney, provides Doc with confidential files that expose the LAPD for funding a hitman. Though Witherspoon is not the star of this film, her performance stands out among the ensemble, especially as one of the only actresses in the cast. Praised by critics but low-earning at the box office, this is an underrated gem in Reese Witherspoon’s filmography and is worth the two-hour commitment.
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8. Freeway (1996)
This black-comedy crime adaptation of “Little Red Riding Hood” stars Reese Witherspoon alongside Kiefer Sutherland and Brooke Shields. Its low budget, brief theatrical release, and positive reviews garnered the film cult status. Witherspoon plays an illiterate teen in South LA whose mother and stepfather are arrested, leading her to steal a social worker’s car and escape to avoid entering the foster care system.
When the car breaks down and Witherspoon is picked up by Bob Wolverton (Sutherland), she begins to trust him, culminating in the revelation that he is a serial killer. As the film ends with Wolverton posing as Witherspoon’s grandmother in her trailer, this “Little Red Riding Hood Adaptation” is clever, funny, intense, and enjoyable the whole way through.
7. Cruel Intentions (1999)
Reese Witherspoon stars alongside Sarah Michelle Gellar and Ryan Phillippe in this teen romantic drama. A cult classic, this film focuses on Kathryn, a manipulative, wealthy high schooler in New York City who dares promiscuous playboy Sebastian to seduce Annette (Witherspoon), the headmaster’s chaste daughter, with the promise of a sexual reward.
When Annette and Sebastian begin to fall in love, Kathryn sabotages their relationship, manipulating Sebastian to lie about his feelings and reject Annette after sleeping with her. When Kathryn is finally exposed, Annette and Sebastian confess their love for each other.
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6. Wild (2014)
This riveting screen adaptation of Cheryl Strayed’s 2012 memoir features a star-studded cast, with Reese Witherspoon taking the lead, who embarks on an 1100-mile hike across the Pacific Crest Trail without any previous hiking experience, searching for clarity and a second chance at becoming the woman her mother raised. Witherspoon proves her versatility in this role, portraying a wayward addict and her impulsive decision to revamp her life with the wilderness as a spiritual guide.
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5. Election (1999)
In this black comedy film, Witherspoon stars alongside Matthew Broderick as a relentlessly ambitious high schooler with student body presidential aspirations. Witherspoon gives a stunning performance as Tracy Flick, and the film’s satirization of high school politics alongside its inappropriate student-teacher relationship vaults this film to the top of Witherspoon’s filmography. Coming at the heels of Broderick’s other successes, Election sets Witherspoon up for success and rightfully garnered critical acclaim both for her acting and the film’s screenplay.
4. The Good Lie (2014)
In this 2014 film, Witherspoon stars as Carrie Davis, an employment counselor who helps a group of Sudanese refugees build their lives in the US, eventually helping them to retrieve another one of their siblings and the Lost Boys of Sudan. Though the plot does not center on Witherspoon’s character, Carrie Davis, binds the siblings together and determines how their lives in the US play out. An underrated member of Witherspoon’s filmography, The Good Lie showcases her versatility and genre-bending.
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3. Pleasantville (1998)
Witherspoon stars in this teen fantasy dramedy alongside Tobey Maguire, with the two portraying siblings who are transported into a 1950s sitcom, Pleasantville. In this alternate reality, Jennifer and David are forced to act as the characters from the show, with Jennifer’s revelations of new information eventually bringing new ideas to the town and turning some of the black-and-white elements to full color.
These changes bring about backlash and a string of arrests, with the black-and-white town leaders curtailing these new changes. However, the town eventually changes and becomes more accepting, prompting Jennifer to stay in Pleasantville when David goes home, only to discover that just half an hour has passed.
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2. American Psycho (2000)
Though Witherspoon does not have a large part in American Psycho, it is a notable film to place on the best Reese Witherspoon movies list. In the film, twenty-seven-year-old Wall Street worker Patrick Bateman surrounds himself with a small group of egotistical and narcissistic people. Bateman holds a high standard for himself, always needing to be superior to those around him. His friends create masks for themselves, but Bateman’s is slightly different, because it hides the greed and disgust within. When those feelings manifest in people surrounding Bateman, he will try to rid them of the world, becoming the American psycho.
1. Walk the Line (2005)
Our last film on the best Reese Witherspoon movies list is Walk the Line, which came out in 2005 and stars Joaquin Phoenix, Reese Witherspoon, and Ginnifer Goodwin. Based on the life of Johnny Cash, the film travels through his life joining the Air Force, proposing to his first love Vivian, and eventually realizing his power with music. While on tour he meets famous singer June Carter (Witherspoon) and starts to fall in love with her, but his addiction to drugs and current wife complicates things, leaving him stranded.
When he convinces June to tour with him again they become even closer, and Cash divorces his first wife, learning to overcome his drug usage with help from June, and proposes to her in front of an audience. Witherspoon’s heartfelt portrayal of June Carter propelled the relationship between Cash and Carter and made this movie memorable and swoon-worthy.
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