Reese Witherspoon has worked her way to Hollywood stardom, transitioning from lighthearted comedies to more challenging dramas. With Witherspoon starring in ‘Wild’ this winter, here’s a look some of her most memorable films.

Fear (1996)

Witherspoon has an early starring role opposite Mark Wahlberg in this thriller about a rebellious teen who falls for a boy with borderline personality disorder. Many a VHS copy of this film became a sleepover staple for years.

Pleasantville (1998)

A pre-Spider-Man Tobey Maguire shared the screen with Witherspoon in this hit comedy-fantasy drama about two siblings who find themselves transported to the idyllic, black-and-white world of their favorite '50s sitcom. 

Cruel Intentions (1999)

Sarah Michelle Gellar joins Witherspoon in this contemporary update of the racy French novel, “Les Liasons Dangereuses.” Witherspoon’s straitlaced schoolgirl character was the target of seduction by her husband-to-be (Ryan Phillipe).

Election (1999)

Witherspoon went head-to-head with Ferris Bueller himself, Matthew Broderick, in this comedy about a high school election that satirized modern politics. She was nominated for a Golden Globe for the role of Tracy Flick.

American Psycho (2000)

In a small but memorable role, the actor plays the fiancee to Christian Bale's Patrick Bateman in this black comedy, based on the popular novel of the same name. Her vapid, self-obsessed character was completely unaware of Bateman's growing insanity and proclivity for murder, despite his use of chainsaws!

Legally Blonde (2001)

‘Blonde’ served as a big boost to the actor’s profile, featuring her in a star-making role as a ditzy sorority girl determined to prove herself as a competent lawyer. Her performance was a hit with audiences and critics; she even earned a Golden Globe nomination for her work.

Sweet Home Alabama (2002)

This charming romantic comedy broke then-box office records and put Witherspoon on the A-List. Here, she plays a successful fashion designer torn between her equally successful fiancé (Patrick Dempsey) and her childhood best friend (Josh Lucas). Lots of sparks, and laughs, ensue.

Walk the Line (2005)

In one of her most impressive roles to date, Witherspoon plays country singer June Carter opposite Joaquin Phoenix's Johnny Cash in this biopic. Her singing voice and stage presence were both spot-on, earning Witherspoon her first Academy Award for Best Actress.

Rendition (2007)

Following the success of ‘Walk the Line,’ Witherspoon ventured into more dramatic territory with this ensemble drama based on true events, centering on the CIA's controversial practice of “extraordinary rendition.” Despite the film’s compelling subject matter, audiences stayed away – but critics were quick to praise Witherspoon’s engaging performance.

Monsters vs. Aliens (2009)

This animated film revolves around a group of monsters and mutated creatures tasked with defending earth from an alien invasion. Witherspoon voices Ginormica, an ordinary woman unwittingly transformed into a 50-foot-tall powerhouse. One of Dreamworks’ more underrated efforts.

This Means War (2012)

Neither a major hit nor a commercial flop, this action comedy stars Chris Pine and Tom Hardy as two CIA agents fighting over the same woman – Reese Witherspoon. Don’t feel bad if you missed this one in theaters; a lot of people did.

Mud (2012)

While ‘Mud’ is best remembered for being the unofficial start of Matthew McConaughey's career renaissance, it also served as a return to form of sorts for Witherspoon. She plays Juniper, the troubled object of the fugitive Mud’s affections, and the source of his many woes. Her understated performance is just one of this film’s many great attributes.

Wild (2014)

In this upcoming biopic, Witherspoon plays the troubled Cheryl Strayed, who embarked on a solo journey to hike the Pacific Crest Trail as a way of putting her past behind her. The role just might put another golden statue in the Oscar-winner’s future.