Reese Witherspoon’s Best Movie Roles: Legally Blonde, Wild and More

From Elle Woods to Melanie Smooter to Annette Hargrove, Reese Witherspoon has enough iconic film roles to make for one movie epic marathon.

After appearing in a handful of TV and film projects throughout the early 1990s, the Tennessee native scored her first major movie role alongside Tobey Maguire in 1998’s Pleasantville. She quickly became a household name for her performances in Cruel Intentions, Legally Blonde and Sweet Home Alabama. She even scored a Best Actress Oscar in 2006 for her role as June Carter Cash in the Johnny Cash biopic Walk the Line.

“I never thought I’d be here in my whole life, growin’ up in Tennessee,” Witherspoon said at the start of her her Oscars acceptance speech. “I want to say that Johnny Cash and June Carter had a wonderful tradition of honoring other artists and musicians and singers. And I really feel that tradition tonight. It is very important and I really feel it. So, I want to thank the Academy for this incredible honor.”

She concluded her speech by stating: “[June] used to say, ‘I’m just tryin’ to matter.’ And, I know what she means, you know. I’m just trying to matter and live a good life and make work that means something to somebody.”

Scroll down to revisit Witherspoon’s biggest movie roles over the years:

‘Pleasantville’ (1998)

The comedy-drama starred Witherspoon and Maguire as siblings who find themselves trapped over the titular 1950s TV show. The pair’s stay in Pleasantville influences the town and its residents, including changing their black-and-white world to color.

‘Cruel Intentions’ (1999)

Witherspoon starred alongside her ex-husband Ryan Phillippe in the teen drama. The film follows Phillippe’s character, Sebastian, as he attempts to seduce Witherspoon’s good girl Annette Hargrove in a bet with his stepsister, Kathryn (Sarah Michelle Gellar), in exchange for sex. However, things take a turn when Sebastian begins to develop real feelings for Annette.

‘Election’ (1999)

The black comedy stars Witherspoon as Tracy Flick, an overachieving high school student whose campaign for student government president gets sabotaged by Matthew Broderick’s Jim McAllister.

‘Legally Blonde’ (2001)

In one of her most iconic film roles, Witherspoon donned several pink outfits to portray sorority girl-turned-Harvard Law student in Legally Blonde and its 2003 sequel, Legally Blonde 2: Red, White & Blonde.

‘Sweet Home Alabama’ (2002)

Witherspoon established herself as a rom-com queen with her role as Melanie Carmichael (née Smooter) in Sweet Home Alabama. The movie follows Melanie as she travels back home to Alabama to finalize her divorce with ex Jake (Josh Lucas). However, her trip home leaves her questioning her big city life and feelings for Jake and her new fiancé, Andrew (Patrick Dempsey).

‘Walk the Line’ (2005)

Both Witherspoon and her costar Joaquin Phoenix scored Oscar nominations for their portrayals of June Carter Cash and Johnny Cash, respectively, in the music biopic. While Witherspoon won in her category, Phoenix ultimately lost to Philip Seymour Hoffman for Capote.

‘Four Christmases’ (2008)

In another memorable rom-com role, Witherspoon and Vince Vaughn starred as a couple who are forced to attend four of their families Christmas celebrations after their planned holiday trip gets cancelled.

‘Wild’ (2014)

Witherspoon scored her second Best Actress Oscar nomination for her portrayal of Cheryl Strayed in Wild. Inspired by real-life events, the biographical film follows Strayed as she looks to overcome person struggles by hiking solo across the Pacific Crest Trail.

‘Home Again’ (2017)

One of Witherspoon’s more recent rom-coms follows a single mother who invites a trio of young aspiring filmmakers to come live in her Los Angeles home, eventually sparking up a romance with one of them (played by Pico Alexander).

‘A Wrinkle in Time’ (2018)

In the Ava DuVernay-directed book adaptation, Witherspoon portrayed Mrs. Whatsit, one of three otherworldly beings who help a young girl named Meg (Storm Reid) on her journey to find her missing father (played by Chris Pine).

‘You’re Cordially Invited’ (2025)

Witherspoon teamed up with the hilarious Will Ferrell in the Prime Video rom-com. Witherspoon and Ferrell star as a sister and a dad whose weddings for their respective loved ones are double-booked at the same venue. The two face hilarious hijinks while ensuring both of their special days go off without a hitch.