1. “Legally Blonde” (2001)

IMDb Rating: 6.3/10
Rotten Tomatoes: 70%

Storyline:
“Legally Blonde” follows Elle Woods, a sorority girl who attempts to win back her ex-boyfriend by getting a law degree. Elle’s journey takes her to the hallowed halls of Harvard Law School. Surrounded by students who ridicule her, Elle becomes determined not only to get her man back but also to prove herself in the process.

Why it’s a Major Performance:
This was Reese’s first leading role in a film, and she immediately steals the room with her larger-than-life portrayal of the effervescent Elle Woods. Her performance not only solidified the public image of Witherspoon as a commanding, humorous leading lady but also served as a testament to her ability to inject depth and emotion into a character that could have been easily dismissed as superficial and one-dimensional.

In “Legally Blonde,” Witherspoon does an exceptional job of balancing humor and heart. Her character undergoes a transformation, and Witherspoon shines in showing that journey, injecting Elle with real emotion and determination beneath her seemingly ditzy exterior. Witherspoon makes us root for Elle, ensuring that the movie’s well-worn message about not judging a book by its cover lands with the audience.

2. “Walk the Line” (2005)

IMDb Rating: 7.8/10
Rotten Tomatoes: 83%

Storyline:
“Walk the Line” explores the early years of Johnny Cash, including his rise to fame, his struggle with drug addiction, and his turbulent relationship with June Carter. Witherspoon plays Carter, a country music singer-songwriter and the future wife of Cash, sharing a volatile yet passionate relationship with him.

Why it’s a Major Performance:
Witherspoon’s portrayal of June Carter garnered her a Best Actress Academy Award. She managed to not only embody the spirit, strength, and vulnerability of Carter, but she also did all her singing, demonstrating her ability to wholly commit to a role and deliver a performance that is both true to life and compellingly watchable.

Reese Witherspoon’s performance in “Walk the Line” demonstrated her versatility as an actress. Her impeccable acting, singing, and her believable Southern accent solidified the portrayal of June Carter Cash as one of her most acclaimed roles. Her character evolves from a strong-willed, independent woman to someone who is deeply in love and conflicted, which, coupled with her exceptional singing, present the depth of Witherspoon’s talent.

3. “Election” (1999)

IMDb Rating: 7.3/10
Rotten Tomatoes: 92%

Storyline:
In “Election,” Witherspoon plays Tracy Flick, a hard-working, fiercely ambitious, and somewhat unlikable high school student running for student body president. The movie is a black comedy that satirizes both the political process and the intense ambition seen in high school.

Why it’s a Major Performance:
Roles like Tracy Flick don’t come often, and Witherspoon delivers a memorable performance by fully embracing Tracy’s ambition and cunning without trying to court sympathy. She manages to keep Tracy’s ruthlessly ambitious character engaging and charismatic, in spite of her being quite unlikable.

Witherspoon’s performance in “Election” marked her breakthrough into more mature roles and established her as a versatile actress capable of balancing drama with biting satire. As Tracy, she brings energy, intensity, and depth to the character, making her one of the most memorable characters in the satire genre. This film remains an essential piece in Witherspoon’s dynamic filmography.

4. “Wild” (2014)

IMDb Rating: 7.1/10
Rotten Tomatoes: 89%

Storyline:
“Wild” is a biographical adventure drama based on Cheryl Strayed’s memoir. Strayed, played by Witherspoon, embarks on a thousand-mile hike on the Pacific Crest Trail as a way to recover from a recent catastrophe. Throughout her journey, she reflects on her past mistakes and learns to self-forgive and grow.

Why it’s a Major Performance:
Witherspoon carries the movie on her shoulders. Strayed’s journey is physically and emotionally exhausting, and Witherspoon’s intimate, raw portrayal makes audiences feel each step with her. “Wild” showcases a vulnerability and grit not often seen in Witherspoon’s roles, providing a compelling examination of self-discovery and healing.

Her acting in “Wild” strips away the charm and the humor that are often associated with Witherspoon, displaying a raw, exposed portrayal of a woman attempting to deal with loss and self-destruction. This performance is unlike anything else in Witherspoon’s filmography, showcasing her remarkable range as an actress and earning her a second Academy Award nomination for Best Actress.

5. “Sweet Home Alabama” (2002)

IMDb Rating: 6.2/10
Rotten Tomatoes: 38%

Storyline:
“Sweet Home Alabama” follows Melanie Carmichael, a successful fashion designer who has reinvented herself as a New York socialite. But when her politician boyfriend proposes, she must return to Alabama to divorce her childhood sweetheart, whom she married young and then abandoned.

Why it’s a Major Performance:
Witherspoon’s charm truly shines in this role, and despite the clichéd storyline, she manages to conjure a warmth and sincerity that makes her character both relatable and engaging. Her portrayal of a woman torn between two worlds and two loves showcases her comedic capabilities alongside her dramatic skills, bringing depth to what could have been a shallow character.

Her capacity to portray both the sophistication of a New York socialite and the authenticity of a Southern girl marks her versatility as an actress. Though “Sweet Home Alabama” is a lighthearted romantic comedy, Witherspoon ensures that her character’s emotional confusion and heartache are palpable. This ability to bring depth to a seemingly frivolous role is a testament to Witherspoon’s acting talent.

6. “Cruel Intentions” (1999)

IMDb Rating: 6.8/10
Rotten Tomatoes: 54%

Storyline:
“Cruel Intentions” is a modern-day adaptation of the classic novel “Dangerous Liaisons,” set among New York City’s teenage elite. Witherspoon plays Annette Hargrove, the new headmaster’s daughter and the embodiment of sexual innocence and sincerity in a world full of cynicism and manipulation.

Why it’s a Major Performance:
Stepping into a role that requires a perfect balance between naivety and strength, Witherspoon gives a superb performance. Her portrayal of Annette besides the manipulative step-siblings played by Ryan Phillippe and Sarah Michelle Gellar gives the film its moral center.

“Cruel Intentions” shows a different side of Witherspoon’s acting skills – her ability to portray a character that radiates kindness and innocence amidst pervasive negativity. Her strong and convincing performance as the virtuous Annette is a testament to her versatile acting talent and her capability to hold her own in a character-driven drama.

7. “Big Little Lies” (2017-2019)

IMDb Rating: 8.5/10
Rotten Tomatoes: 89%

Storyline:
“Big Little Lies” is not a movie but an acclaimed HBO miniseries. It follows a group of wealthy mothers in Monterey, California, whose seemingly perfect lives unravel to the point of murder. Witherspoon plays Madeline Mackenzie, a seemingly perfect mother with a fierce personality and a tendency to get involved in other people’s business.

Why it’s a Major Performance:
As the comically frantic and overbearing Madeline, Witherspoon delivers a stunning and compelling performance that foregrounds her versatility and depth as an actress. She convincingly portrays a character that is grappling with the pressures of maintaining the ideal lifestyle and the perfect marriage.

Her portrayal of Madeline provides an incisive critique of the expectations placed on women and the pressures of maintaining appearances in a highly judgmental society. Witherspoon’s performance pulls no punches in displaying Madeline’s flaws and complexity, resulting in one of the most nuanced and compelling characters in recent TV history.

8. “The Man in the Moon” (1991)

IMDb Rating: 7.4/10
Rotten Tomatoes: 89%

Storyline:
In her debut film, Witherspoon stars as Dani Trant, a 14-year-old girl in 1950s Louisiana, experiencing her first love and the inevitable heartbreak that follows. As she navigates adolescence, Dani learns about love, loss and the nuances of human relationships.

Why it’s a Major Performance:
Her debut role in “The Man in the Moon” demonstrated from the very outset that Witherspoon was a burgeoning talent. Even from a young age, she showcases her ability to portray a range of emotions with nuance and maturity. Her role as Dani was widely praised as a sensitive and poignant portrayal of adolescence.

Reese manages to carry the emotional weight of the film, and her impressive performance demonstrated an innate ability to genuinely convey a character’s emotional journey. Her performance stands as a significant and captivating introduction to an actress who would later become one of Hollywood’s most respected and popular.

9. “Little Fires Everywhere” (2020)

IMDb Rating: 7.8/10
Rotten Tomatoes: 78%

Storyline:
Like “Big Little Lies,” this is not a film but a miniseries that takes place in the 1990s and explores motherhood, race, belonging, and privilege. Reese plays Elena Richardson, a wealthy mother of four who lives by the rules until a nomadic single mother disrupts her ordered life.

Why it’s a Major Performance:
Challenged by the contrast of Elena’s apparently perfect life and her internal dissatisfaction, Reese demonstrates her excellent range as an actress. Through Elena, Reese explores a more flawed, often unsympathetic character, different from the roles she usually picks, underlining her versatility as an actress once again.

Reese’s confrontation of issues of race, identity, and privilege in “Little Fires Everywhere” present a transformation in her career trajectory. She uses her platform to bring thought-provoking content to the audience, invoking conversations on important societal issues.

10. “Pleasantville” (1998)

IMDb Rating: 7.5/10
Rotten Tomatoes: 85%

Storyline:
“Pleasantville” follows the story of two ’90s American teenagers who are transported back into the world of a black-and-white ’50s sitcom. Witherspoon plays Jennifer, a quintessential ’90s high school girl who, along with her brother, disturbs the idyllic world of Pleasantville with ideas of individualism and rebellion.

Why it’s a Major Performance:
Reese Witherspoon stood out in her role as Jennifer, a character that develops from a superficial teenager to a young woman who appreciates books and knowledge. The evolution of Jennifer’s character and Witherspoon’s stellar performance added several layers to this fantasy comedy-drama.

“Pleasantville” was a turning point in Witherspoon’s career as it gave her a chance to showcase her talent in a unique and unconventional narrative. Her acting was praised for its depth and intelligence, firmly establishing her early on as a force to be reckoned with in Hollywood.