For more than thirty years, Reese Witherspoon has 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 the most 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 like Freeway right through to her Academy Award-winning performance in Walk 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 as Wild.

10 Sing (2016)

Reese Witherspoon as Rosita

Although not primarily known for her voiceover work, Reese Witherspoon has had several roles in animated features like The Trumpet of the Swan and Monsters vs. Aliens. However, her greatest voice role came as Rosita, the dissatisfied housewife and mother of 25 piglets, in the jukebox musical Sing. 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 as Rosita 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, Sing was a crowd-pleasing comedy for viewers of all ages. Witherspoon’s role was a particular highlight, and she returned to reprise Rosita for Sing 2.

9 Just Like Heaven (2005)

Reese Witherspoon as Elizabeth

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 comedy Just 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 Heaven rose above its outrageous narrative to deliver a heartfelt rom-com. While it may not be as well-known as the best 2000s rom-coms, it’s well worth checking out for lovers of a good fantasy-based romance.

8 Freeway (1996)

Reese Witherspoon as Vanessa Lutz

Reese Witherspoon gave a spellbinding performance as Vanessa Lutz in the black comedy Freeway. As a dark retelling of the Brothers Grimm story “Little Red Riding Hood,” Freeway took 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, Freeway had 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, Freeway truly got the best out of Witherspoon, which was an earlier indication of her incredible star power. Although it was a box office bomb upon release, Freeway has since gained a cult following due to its wicked sense of humor and accomplished campy style.

7 Cruel Intentions (1999)

Reese Witherspoon as Annette Hargrove

The steamy teen romance Cruel Intentions was a modern telling of Pierre Choderlos de Laclos' 1782 novel Les 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 heaster’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 Intentions was the kind of erotic-fueled movie that isn’t really produced for mainstream audiences anymore. While Laclos's novel had already been adapted as Dangerous Liaisons in 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 Intentions also led to the development of an unlikely franchise.

6 Pleasantville (1998)

Reese Witherspoon as Jennifer / Mary Sue Parker

While the domestic bliss portrayed in 1950s sitcoms like Leave It To Beaver and I Love Lucy look aspirational, the truth behind these portrayals was explored in the 1990s teen fantasy Pleasantville. 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, Pleasantville was 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 and refusing to conform to Pleasantville’s stifled 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.

5 Inherent Vice (2014)

Reese Witherspoon as Deputy District Attorney Penny Kimball

Reese Witherspoon reunited with her Walk the Line co-star Joaquin Phoenix for Paul Thomas Anderson’s outrageous neo-noir mystery Inherent Vice. Based on the book by the notoriously dense and cryptic writer Thomas Pynchon, Inherent Vice saw 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 itted that Inherent Vice made 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 Vice once showcased his ability to capture the 1970s as he had done previously in Boogie Nights and would later achieve with Licorice Pizza. Inherent Vice was truly weird, uniquely funny, and one of the most underrated movies of the 2010s.

4 Wild (2014)

Reese Witherspoon as Cheryl Strayed

The biographical drama Wild was 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. Wild showcased 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 on Wild, which was the first film made with her production company Pacific Standard, now known as Hello Sunshine. Witherspoon described Wild as “the hardest movie I've ever made in my life” (via Vulture) 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 gave Wild a realistic and believable feeling, which, mixed with the emotional intensity of Witherspoon’s performance, made for a truly effective story.

3 Election (1999)

Reese Witherspoon as Tracy Flick

With a combination of dark humor and some truly intelligent writing, Election was 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, Election was 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 (via Huff Post) that President Barack Obama told him Election was his favorite political film. With so many accolades and recommendations to consider, it’s clear that Election was a must-watch entry in Witherspoon’s impressive filmography.

2 Walk The Line (2005)

Reese Witherspoon as June Carter

The life story of country music legend Johnny Cash was told in the unmatched biopic Walk 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 Line was 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 Line was 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.

1 Legally Blonde (2001)

Reese Witherspoon as Elle Woods

Reese Witherspoon was perfectly cast as Elle Wood in Legally 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 of Legally Blonde rested firmly on Witherspoon’s performance, which exuded sunny energy and made her character impossible not to like. With a clever and engaging script, Reese Whitherspoon elevated this material through a cheerful performance and impeccable comedic timing. A sequel titled Legally Blonde 2: Red, White & Blonde was released in 2003 and an prequel series titled Elle is set for release in 2025, proving interest in Legally Blonde has not waned in the more than 20 years since it was released.

Sources: Vulture, Huff Post