For more than thirty years,Reese Witherspoonhas been at the forefront of Hollywood with incredible roles in comedies, biopics, and dramas. Known for her small stature and large performances, Witherspoon’s incredible likability and onscreen charisma have made her a household name. While Witherspoon has often been associated with lighthearted performances in beloved rom-coms, she’s excelled with impressively poignant and emotional turns in powerful biopics and insightful dramas.
As one of themost iconic actresses of the 1990s, Witherspoon’s career has gone from strength to strength over the past three decades. From impressive early turns in underrated satirical comedies likeFreewayright through to herAcademy Award-winning performance inWalk the Line, Witherspoon has showcased her skills across various genres. Witherspoon has even created her own opportunities through her production company, Hello Sunshine, where she has produced and starred in several female-led productions, such asWild.
Sing (2016)
Although not primarily known for her voiceover work, Reese Witherspoon has had several roles in animated features likeThe Trumpet of the SwanandMonsters vs. Aliens. However, her greatest voice role came as Rosita, the dissatisfied housewife and mother of 25 piglets, in the jukebox musicalSing. This family-friendly film was set in a world inhabited by anthropomorphic animals. The female pig Rosita took part in the movie’s singing competition, where she competed for a $1,000 prize.
With a talented ensemble cast that included the likes of Matthew McConaughey, Seth MacFarlane, and Scarlett Johansson, Witherspoon’s role was the emotional center of the film asRosita found meaning away from her busy life as an overloaded mother in a world of music and excitement. With impressive animation, an infectious sense of humor, and a warm, poignant narrative,Singwas a crowd-pleasing comedy for viewers of all ages. Witherspoon’s role was a particular highlight, and she returned to reprise Rosita forSing 2.
Just Like Heaven
Cast
Just Like Heaven tells the story of a man who begins to fall in love with the spirit of a woman he meets in his apartment. As he grapples with the supernatural elements of their connection, he strives to unravel the mystery surrounding her existence. This romantic comedy blends elements of fantasy with heartfelt moments of human connection.
No genre suits Reese Witherspoon’s unique cinematic charm better than a rom-com, which was proved by her role in the highly underrated 2000s comedyJust Like Heaven. With Witherspoon as Elizabeth, a busy doctor with no time to date, and Mark Ruffalo as David, the man who moved into her apartment, it’s only natural that romance would blossom between the pair. However, things weren’t quite so straightforward, as Elizabeth was in a car accident, and it was her spirit that was haunting the apartment of its new tenant.
This unique concept proved the perfect template for comedic gold as Witherspoon and Ruffalo butt heads, only to soon find themselves falling for one another. With plenty of tongue-in-cheek humor and a self-aware understanding of how ridiculous its story was,Just Like Heavenrose above its outrageous narrative to deliver a heartfelt rom-com. While it may not be as well-known asthe best 2000s rom-coms, it’s well worth checking out for lovers of a good fantasy-based romance.
Freeway
Freeway is a dark comedy thriller that reimagines Little Red Riding Hood in modern-day America. The film follows Vanessa Lutz as Vanessa, a teenage girl who is trying to visit her grandmother in a nearby town. Along the way, she encounters Bob Wolverton, a charming but sinister stranger played by Kiefer Sutherland.
Reese Witherspoon gave a spellbinding performance as Vanessa Lutz in the black comedyFreeway. As a dark retelling of the Brothers Grimm story “Little Red Riding Hood,”Freewaytook things into much darker territory as Witherspoon played an illiterate teenager evading foster care after her drug-addicted mother was arrested for prostitution. On her way to seek refuge with her grandmother, Vanessa meets Bob Wolverton (Kiefer Sutherland), a despicable serial killer who at first seemed helpful before turning sinister and getting shot in the face by Witherspoon.
With many twists and turns,Freewayhad a unique sense of humor as it effortlessly shifted through genres, including coming-of-age teen comedy, serial killer horror, and, eventually, courtroom drama. From writer and director Matthew Bright,Freewaytruly got the best out of Witherspoon, which was an earlier indication of her incredible star power. Although it wasa box office bombupon release,Freewayhas since gained a cult following due to its wicked sense of humor and accomplished campy style.
Cruel Intentions
With a screenplay and direction by Roger Kumble, Cruel Intentions is a Romance and Teen Drama film that stars Selma Blair, Sarah Michelle Gellar, Reese Witherspoon, and Ryan Phillippe. The plot revolves around a group of teens, with a man betting one of them that he can seduce a girl successfully.
The steamy teen romanceCruel Intentionswas a modern telling of Pierre Choderlos de Laclos' 1782 novelLes Liaisons Dangereuses, a story of deep corruption and depravity. With a star-studded cast including Sarah Michelle Gellar, Selma Blair, and Reese Witherspoon, this cult film saw two vicious step-siblings conspiring to ruin an elite Manhattan headmaster’s daughter who staunchly opposes sex before love. As Annette Hargrove, Witherspoon perfectly captured the girl-next-door charm of the seemingly eternally virginal object of Ryan Phillippe’s underhanded desires.
With hormones raging and a wonderfully twisted story,Cruel Intentionswas the kind of erotic-fueled movie that isn’t really produced for mainstream audiences anymore. While Laclos’s novel had already been adapted asDangerous Liaisonsin 1988 with Glenn Close and John Malkovich, this teen reimagining added to its sensual appeal. With a sequel, prequel, and even a jukebox musical,Cruel Intentionsalso led to the development of an unlikely franchise.
Pleasantville
Pleasantville is a drama that explores themes of change and self-discovery, as two modern teenagers find themselves transported into a 1950s television show. The movie delves into social issues and individual freedoms, highlighting the contrast between the idealized past and the complexities of the real world. With its unique premise, Pleasantville offers a thought-provoking narrative on the impact of transformation on a seemingly perfect society.
While the domestic bliss portrayed in 1950s sitcoms likeLeave It To BeaverandI Love Lucylook aspirational, the truth behind these portrayals was explored in the 1990s teen fantasyPleasantville. With Reese Witherspoon and Tobey Maguire as twin siblings transported into a black-and-white 1950s TV sitcom, this unique film addressed the stark difference between fact and fiction and the drawbacks of romanticizing a fantasy world. Addressing themes of personal and political repression,Pleasantvillewas a tongue-in-cheek look at contemporary American society.
Witherspoon’s performance as Jennifer, the hot-headed sister who takes the place of the timid good girl Mary Sue Parker in Pleasantville,was the perfect contrast to the repressed tendencies of the idyllic fictional town. By flaunting her modernity andrefusing to conform toPleasantville’sstifled sexual expectations, she brought color to the black-and-white world and shook the community’s values to their core. Witherspoon was perfectly cast as Jennifer and carefully walked the fine line between 1950s faux innocence and modern rebellion.
Inherent Vice
Based on Thomas Pynchon’s novel, Inherent Vice is a noir-crime film that puts viewers in the perspective of private eye Doc Sportello during the 1960s, who fully embraces the hippie lifestyle while trying to do his job. When his former girlfriend and her new billionaire boyfriend go missing, Doc immerses himself in the depths of Los Angeles’s crime-laden underworld to solve the cases.
Reese Witherspoon reunited with herWalk the Lineco-star Joaquin Phoenix for Paul Thomas Anderson’s outrageous neo-noir mysteryInherent Vice. Based on the book by the notoriously dense and cryptic writer Thomas Pynchon,Inherent Vicesaw Phoenix portray the stoner hippie private detective Doc Sportello trying to uncover three disappearances in 1970 Los Angeles. Witherspoon played the district attorney with a soft spot for hippies having a fling with Doc, who provided him with confidential files to help with his case.
While it must be admitted thatInherent Vicemade for convoluted and confusing viewing, like the best film noirs, it was the journey and not the destination that mattered in this complex and slowly unraveling mystery. From director Anderson,Inherent Viceonce showcased his ability to capture the 1970sas he had done previously inBoogie Nightsand would later achieve withLicorice Pizza.Inherent Vicewas truly weird, uniquely funny, and one of the most underrated movies of the 2010s.
Wild
Wild follows a woman embarking on a transformative journey along the Pacific Crest Trail. Driven by the desire to overcome her troubled past, she undertakes a solo hike of over a thousand miles, facing personal challenges and gaining introspective insights along the way.
The biographical dramaWildwas based on Cheryl Strayed’s memoir of adventure, grief, and recovery as she embarked on a 1,100-mile hike on the Pacific Crest Trail to overcome her difficult personal problems. As Cheryl, Witherspoon captured the longing and searching within her character as she struggled with the death of her mother and tried to numb her pain with heroin use and mindless sex.Wildshowcased how renewed determination and an adventurous spirit helped Cheryl rose out of her difficult circumstances to once again find purpose in life.
Witherspoon also acted as a producer onWild, which was the first film made with her production company Pacific Standard, now known as Hello Sunshine. Witherspoon describedWildas “the hardest movie I’ve ever made in my life” (viaVulture) as they filmed in remote locations while she and the crew “pulled each other up the mountains and carried each others' equipment.” However, it was these natural settings that gaveWilda realistic and believable feeling, which, mixed with the emotional intensity of Witherspoon’s performance, made for a truly effective story.
Election
Directed by Alexander Payne, 1999’s Election is a Dark Comedy involving a high school election, focusing on the president of the student body. The film stars Matthew Broderick as a High School Social Studies teacher that ends up heading a scheme to disparage a popular girl (played by Reese Witherspoon) from winning the election.
With a combination of dark humor and some truly intelligent writing,Electionwas one of the most underrated comedies of the 1990s. With Reese Witherspoon as the overarching high schooler Tracy Flick and Matthew Broderick as her teacher determined to sabotage her candidacy for student government president, this engaging political satire showcased how the cutthroat nastiness of politics can easily find their way into the realm of high school elections.
Boasting one of Withspoon’s very best performances,Electionwas not a commercial hit upon release. However, it fared better with critics and achieved an Academy Award nomination for Best Adapted Screenplay. Director Alexander Payne has also revealed (viaHuff Post) that President Barack Obama told himElectionwas his favorite political film. With so many accolades and recommendations to consider, it’s clear thatElectionwas a must-watch entry in Witherspoon’s impressive filmography.
Walk The Line
Walk the Line is a biographical drama film that tells the story of Johnny Cash, a legendary musician, and his tumultuous relationship with June Carter, a country singer. The film stars Joaquin Phoenix as Cash and Reese Witherspoon as Carter, and explores their romance, as well as Cash’s struggles with addiction and fame.
The life story of country music legend Johnny Cash was told in the unmatched biopicWalk the Line,starring Joaquin Phoenix and Reese Witherspoon. The star-crossed lovers Johnny and June Carter had a whirlwind romance with plenty of ups and downs made all the more difficult by the country icon’s excessive use of drugs and alcohol. As June, Witherspoon captured the emotional turmoil of watching Johnny destroy himself and the challenges of trying to reconcile their fractured relationship.
Walk the Linewas as much the story of June’s hardships loving Johnny, and Witherspoon earned the Academy Award for Best Actress for her extraordinary performance. A country legend in her own right, it was thrilling to watch how Johnny’s personal issues and their tumultuous relationship inspired June to write one of his most famous songs, “Ring of Fire.”Walk the Linewas the perfect example of what a great biopic can achieve, as it turned new listeners on the legacy of Johnny Cash and pleased longtime lovers of the Man in Black.
Legally Blondes
Legally Blondes is a 2009 family comedy spin-off from the Legally Blonde film series. Directed by Savage Steve Holland, the film follows British twin sisters Izzy and Annie Woods, played by Camilla and Rebecca Rosso, as they navigate the challenges of attending a prestigious private school in California. The twins face social and academic obstacles that test their ingenuity and resilience. The movie centers on themes of fitting in and standing up for oneself.
Reese Witherspoon was perfectly cast as Elle Wood inLegally Blonde, her definitive movie and her most recognizable character. As the story of a seemingly ditzy and underachieving sorority girl attempting to win back her boyfriend by gaining a Harvard Law degree, this beloved rom-com addressed the stereotype of dumb blondes and the idea that just because someone is interested in beauty and fashion that does not mean they’re automatically dumb. While pursuing her degree, Elle confounded everybody’s expectations of her to prove she was anything but dim.
The success ofLegally Blonderested firmly on Witherspoon’s performance, which exuded sunny energy and made her character impossible not to like. With a clever and engaging script,Reese Whitherspoonelevated this material through a cheerful performance and impeccable comedic timing. A sequel titledLegally Blonde 2: Red, White & Blondewas released in 2003 and an upcoming prequel series titledElleis set for release in 2025, proving interest inLegally Blondehas not waned in the more than 20 years since it was released.
