Reese Witherspoon at a movie premiere in 2022

Reese Witherspoon at a movie premiere in 2022 (Photo by lev radin on Shutterstock)

From rom-com darling to Oscar winner, Reese Witherspoon has captivated audiences for decades with her infectious charm and undeniable talent. Whether she's Elle Woods outsmarting Harvard Law or Cheryl Strayed finding her way on the Pacific Crest Trail, Witherspoon brings a powerful presence to every role. But with a filmography packed with unforgettable characters, choosing the best Reese Witherspoon movies can feel like a daunting task. Worry not, movie lovers! We've sifted through her impressive career to present you with the must-see films that showcase the full range of her brilliance. Get ready for a journey filled with laughter, tears, girl power, and unforgettable performances! Which titles in the esteemed actress's repertoire stand out above the rest? Luckily, we at EdNews have researched across 10 expert sources to bring you the top five best Reese Witherspoon movies of all time! Don't agree with our list? We would love to hear from you in the comments below!

The List: Best Reese Witherspoon Movies, According to Her Fans

1. “Election” (1999)

While Witherspoon has played her fair share of “Type A” characters throughout her career, none are as iconic as her role in “Election.” Remember when Reese Witherspoon ruled the high school halls with an iron fist (and a perfectly manicured planner)? Yep, we're talking about her iconic role as Tracy Flick in Alexander Payne's hilarious dark comedy.

ScreenRant gushes about this flick, calling it a must-watch for anyone who ever felt the pressures of high school (or the sheer joy of a good underdog story). Witherspoon steals the show as Tracy, the overachiever we all knew and maybe even secretly loved to hate. Her ambition is as sharp as her perfectly lined pencils, and her win-at-all-costs attitude is both hilarious and a little terrifying (think “Legally Blonde” meets “House of Cards”).

One minute you're laughing out loud at Tracy's uptight antics, the next you're wondering if she's secretly plotting world domination (with color-coded charts, of course). This role not only launched Witherspoon's comedic career but also scored her a well-deserved Golden Globe nomination (Parade).

GoldDerby even goes so far as to say Tracy Flick is a cultural phenomenon. Her name has become synonymous with cutthroat ambition, and her dedication to the cause (in this case, high school student body president) is as relentless as it is entertaining. But “Election” is more than just a one-woman show. The film cleverly weaves in themes of real-world politics and the lengths people will go to in the name of power. So grab some popcorn, settle in, and prepare to be equal parts amused and horrified by the one and only Tracy Flick.

2. “Walk the Line” (2005)

While Johnny Cash's famous ditty “Walk the Line” may not have been written for June Carter, we certainly would “walk the line” for Reese Witherspoon's portrayal of the iconic rockabilly singer any day. In 2005 Reese Witherspoon took a dramatic turn and absolutely slayed it! Cosmopolitan spills the tea on her powerful performance as June Carter Cash in this biopic: June was a firecracker on stage, and Witherspoon perfectly captured that energy, but the film also dives deep into the struggles behind the music.

MovieWeb agrees, raving about Witherspoon's Oscar-winning portrayal. They call “Walk the Line” an incredible journey, following Johnny Cash from his cotton-farming roots to superstardom, with all the messiness in between (including his addiction issues). But the true magic lies in the chemistry between Witherspoon and Joaquin Phoenix, who plays Johnny Cash. Their on-screen spark is undeniable, making this a must-watch for music lovers and movie buffs alike.

Parade magazine takes it a step further, calling Witherspoon's performance a masterclass in acting. She flawlessly embodies June's contrasting personalities - the bubbly performer and the complex woman with hidden depths. And let's not forget the singing! Both Witherspoon and Phoenix belted out their own tunes, adding another layer of authenticity to this powerhouse film. Witherspoon wasn't even 30 yet when she snagged the Best Actress Oscar for this role, proving she's a force to be reckoned with on and off the stage.

3. “Legally Blonde” (2001)

I mean, what's your first thought when you hear the name Reese Witherspoon? Because for us, it's Elle Woods, of course. Dust off your bend and snap skills, because we're celebrating the iconic film that launched Reese Witherspoon into superstardom! This hilarious 2001 classic, as RadioTimes points out, is more than just a fun rewatch – it's a girl power anthem that continues to inspire generations.

Who can forget Elle Woods, the sorority girl with a heart of gold and a wardrobe full of pink? Dumped by her boyfriend Warner for not being “serious” enough, Elle decides to prove him wrong by following him to Harvard Law. The Pioneer Woman describes Elle's journey from underestimated underdog to legal powerhouse. Armed with her signature style, unwavering wit, and surprising intellect, Elle dismantles the “dumb blonde” stereotype one courtroom victory at a time.

This is more than just a rom-com. With Witherspoon's powerhouse performance leading the charge, Elle becomes the unlikely heroine we all root for. She proves that intelligence and femininity can go hand-in-hand, and that sometimes, the most underestimated people can achieve extraordinary things. So grab your best friend, whip up a batch of courthouse-worthy margaritas, and get ready to cheer Elle on as she conquers Harvard Law (and maybe even Warner's heart) in this timeless classic (Wide Open Country).

4. “Pleasantville” (1998)

While on the outside, this movie may just look like another dramatic comedy, deep down, “Pleasantville” is a film that explores the power of self-expression and challenging societal norms. Imagine flipping the channel and getting sucked right into your favorite TV show! That's the wild premise of “Pleasantville,” a movie that blends fantasy, drama, and teen angst into one quirky masterpiece, according to SnipDaily. Reese Witherspoon teams up with Tobey Maguire as siblings who get magically transported into a squeaky-clean 1950s sitcom.

Parade describes the film's journey as both hilarious and thought-provoking. While the initial black-and-white world might seem like a fun throwback, things get interesting when Jennifer (Witherspoon) starts shaking things up. Her modern-day ideas and experiences bring a splash of color to the town, both literally and metaphorically. It's a wild ride of self-discovery, with a surprising amount of depth hidden beneath the sitcom facade.

GoldDerby throws a bit of shade, calling the film a “gimmicky novelty act” that somehow manages to work. Witherspoon's Jennifer is the outgoing rebel, and her clash with the picture-perfect Pleasantville world is what sparks the transformation. While some reviewers might scoff at the premise, they can't deny Witherspoon's signature charm that shines through even in a poodle skirt! So next time you're binge-watching a series, remember – that perfect world on TV might not be all it's cracked up to be.

5. “Wild” (2014)

“Wild” shows Witherspoon once again doing what she does best: playing strong, independent women. And much like the role that garnered her first Oscar nomination and win, she is once again telling a real person's story.

This movie will leave you equal parts awestruck and inspired. Based on Cheryl Strayed's powerful memoir, “Wild” follows her solo trek along the Pacific Crest Trail, a mammoth 1,100-mile journey. Wide Open Country tells us this wasn't just a hike; it was a chance for Cheryl (played by Witherspoon) to heal after a series of personal losses.

The film shines brightest when Witherspoon is alone on the trail, ScreenRant explains. With just her thoughts and the wilderness for company, she delivers a raw and deeply personal performance. We see the physical and emotional toll of the hike etched on her face, but also a quiet determination to overcome her grief. This vulnerability earned Witherspoon well-deserved Oscar buzz, proving she can handle serious drama just as effortlessly as rom-coms.

CinemaBlend calls “Wild” one of Witherspoon's boldest performances. She doesn't shy away from portraying Cheryl's flaws and struggles, making her journey all the more relatable. The film doesn't sugarcoat the challenges Cheryl faces, but it also captures the profound beauty of self-discovery that comes from pushing yourself to the limit. With Witherspoon at the helm, this is a captivating character study that will stay with you long after the credits roll. So grab some tissues, lace up your metaphorical hiking boots, and get ready to be swept away by Cheryl's powerful story.

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Note: This article was not paid for nor sponsored. EdNews is not connected to nor partnered with any of the brands mentioned and receives no compensation for its recommendations. This article may contain affiliate links in which we receive a commission if you make a purchase.

About Jilly Hite

Janelle is a freelance writer from New York. Her writing focuses on parenting, tech, business, interior design, education, and telling people’s inspiring stories. Janelle has written for Mustela and Newton Baby and has bylines in Pregnant Chicken, Syracuse Woman Magazine, the Baldwinsville Messenger, and Family Times Magazine. She holds a master’s degree in literacy from the State University of New York at Oswego.

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