Actress Reese Witherspoon is the woman of the hour in Hollywood. She is an Oscar winner who has been delivering incredible performances onscreen since audiences can remember. Witherspoon has had plenty of memorable roles so far, which have ranged from villainous to heroic.

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In recent years, the actress has also ventured into television and online streaming. In fact, Witherspoon currently produces and stars in Apple TV+’s The Morning Show, which is reportedly among the most expensive TV shows ever made.

Inherent Vice, 74%

Penny Kimball sitting on a bench next to Don in Inherent Vice.

Inherent Vice boasts a cast that includes Witherspoon, Josh Brolin, Owen Wilson, Benicio del Toro, and Joaquin Phoenix. The film’s story revolves around a stoned private detective portrayed by Phoenix who is contacted by a former lover after learning that her current beau may end up in a mental hospital.

The actors’ performances in the film were praised. However, some critics have said that it stayed too faithful to the novel it was based on. Nonetheless, there is also some consensus that Inherent Vice is one of the most underrated movies of the decade.

Freeway, 76%

Bob holds a frightened Vanessa in Freeway

The film is a modern take on the tale of Little Red Riding Hood, in which Witherspoon’s Vanessa Lutz seeks out her estranged grandmother after the arrest of her mother. In doing so, Vanessa accepts a ride from a school counselor, who turns out to be the I-5 killer.

The film features Kiefer Sutherland as the I-5 killer (or the Big Bad Wolf). The cast also includes Brooke Shields, Bokeem Woodbine, and the late Brittany Murphy. The film is directed by Matthew Bright, who told Punk Globe that Witherspoon was a “revelation” when he started shooting with her.

Walk The Line, 82%

June and Johnny look at each other on stage in Walk the Line

It’s always tricky when you have to portray a real-life person on the big screen. In Walk the Line, Witherspoon transforms into June Carter Cash to play opposite Joaquin Phoenix’s Johnny Cash. In the beginning, she didn’t know the role would have some singing involved.

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“First of all, I didn’t know I was singing,” the actress told LiveAbout.com. “I signed up to do the acting bit. That would have been in a completely different contract.” Meanwhile, one of the things you didn't know from behind the scenes of Walk The Line is that Witherspoon also had to learn to play the autoharp, which was “really difficult.”

Pleasantville, 85%

A scene from Pleasantville with Tobey Maguire and Reese Witherspoon.

The 1998 film is a comedy-drama wherein two siblings get transported into a black-and-white TV show with the help of a device. Once they found themselves on the show, the siblings assume the roles of two characters in the series. Little did they know that this also had some effect on their own town.

Aside from Witherspoon, the cast also includes Tobey Maguire and the late Paul Walker. Meanwhile, William H. Macy, Joan Allen, and Jeff Daniels portray some of the other picture-perfect characters in Pleasantville. Back in 2018, Witherspoon took to Instagram to celebrate the film’s 20th anniversary.

This Changes Everything, 87%

Unlike the other films on this list, This Changes Everything happens to be a documentary in which several prominent women in Hollywood come together and confront the issue of gender disparity.

Aside from Witherspoon, actresses such as Meryl Streep, Cate Blanchett, Natalie Portman, and Jessica Chastain also appear in the film. Meanwhile, serving as executive producer is veteran actress Geena Davis, who told NPR that she was “very upset and angry at that [gender disparity] happening to me.”

Wild, 88%

Reese Witherspoon with a backpack in Wild

This 2014 film is based on the true story of Cheryl Strayed, who once decided to hike the Pacific Crest Trail all by herself. As it turns out, Witherspoon knew of Strayed’s experience, even before her memoir was published.

While speaking with Collider, the actress revealed, “I first read the manuscript when Cheryl sent it to me, right before it was published.” Witherspoon noted it was a “fascinating read” and once she was done, she knew she had to turn the manuscript into a film. Aside from Witherspoon, the film also stars Oscar winner Laura Dern as Cheryl’s mother.

The Good Lie, 88%

In this 2014 film, Witherspoon portrays an employment agency counselor who assists a group of Sudanese refugees with their resettlement in the U.S. Aside from Witherspoon, the film also stars Ger Duany, who is a Sudanese refugee himself.

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While speaking with Collider, Guany recalled, “There was too much gambling with my life. I don’t know why I’m here.” The film may feature Witherspoon prominently in its promotion, but according to reports, she only appears in the film for a total of 35 minutes. Nonetheless, she delivers a powerful performance.

The Man In The Moon, 90%

This 1991 film marks Witherspoon’s big-screen debut and even today, it still ranks as one of Witherspoon’s best films, according to IMDb.

The Man in the Moon is a coming of age story about two close siblings whose relationship is put to the test after they both get involved with the same young boy. Working on the film resulted in a “magical summer” for Witherspoon. However, she also told Entertainment Weekly, “I had to kiss a boy onscreen for the first time, and I was 14 years old and I was so embarrassed.”

Election, 92%

Election is another critically acclaimed film that Witherspoon worked on when she was younger. The film is set in a high school in which overachiever Tracy Flick (played by Witherspoon) is determined to win the school's election, no matter the cost.

Once she finds herself up against the high school jock, it's no holds barred for Tracy. The film also includes a great performance by Matthew Broderick and it's well worth a watch for any fan of Reese Witherspoon.

Mud, 97%

Reese Witherspoon on the phone in her bed in Mud

The 2012 film continues to be Witherspoon’s highest-rated film on Rotten Tomatoes today. Mud is the story of a fugitive, played by Matthew McConaughey, whose only concern is reuniting with the love of his life, played by Witherspoon.

While making the film, it was also revealed that McConaughey and Witherspoon had stark different living arrangements. Witherspoon ended up staying at a motel, where she thrived on a daily McDonald’s diet. Meanwhile, McConaughey stayed in his trailer and feasted on some barbecue. The actor even sent Witherspoon a photo as proof, according to Yahoo Entertainment.

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